WO2023028708A1 - Water-soluble cannabinoid compositions, methods of making and use - Google Patents

Water-soluble cannabinoid compositions, methods of making and use Download PDF

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Publication number
WO2023028708A1
WO2023028708A1 PCT/CA2022/051320 CA2022051320W WO2023028708A1 WO 2023028708 A1 WO2023028708 A1 WO 2023028708A1 CA 2022051320 W CA2022051320 W CA 2022051320W WO 2023028708 A1 WO2023028708 A1 WO 2023028708A1
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Prior art keywords
peg
polyglyceryl
oil
composition
surfactant
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PCT/CA2022/051320
Other languages
French (fr)
Inventor
Ben GEILING
Mark Hetherington
Anusha Geethangani Perera SAMARANAYAKA
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Canopy Growth Corporation
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Publication of WO2023028708A1 publication Critical patent/WO2023028708A1/en

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/38—Other non-alcoholic beverages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates

Definitions

  • the present disclosure generally relates to water-soluble cannabinoid and/or terpene compositions, and more particularly to compositions comprising cannabinoids and/or terpenes that may be used in the preparation of beverages, topicals, foodstuffs, and other products.
  • Cigarette smoking has been linked to devastating health risks thought to result from the formation of harmful combustion products.
  • legislation exists which prohibits smoking in various locations and cannabis smoking itself is the target of regulation due to so-called “second hand smoke” risks, as well as what is said to be unpleasant smells for some people.
  • Methods for consuming cannabis, and more particularly cannabinoids, which do not involve smoking or other vaporous means of ingestion may therefore be advantageous as such methods do not involve these and other unwanted effects.
  • Oral consumption comprises a significant percentage of total cannabis use in federally legal jurisdictions as well as on a state, province, or the like, basis globally.
  • Many orally consumable products may contain unhealthy amounts of substances other than cannabinoids.
  • many known oral products use expensive additives, which are cost prohibitive and may also have unpredictable supply.
  • cannabinoids present challenges for preparing desirable consumer products, such as beverages and other foodstuffs.
  • Cannabinoids including many cannabinoid extracts and oils, are insoluble in water thereby making many food products and beverages difficult to produce, including difficulties in obtaining desirable concentrations, dispersibility, and stability of cannabinoids in these products.
  • Emulsions of cannabinoids have been used, but challenges arise in obtaining compositions capable of providing desirable particle size distribution characteristics. These factors are particularly relevant in preparing consumer products having high ionic strengths (e.g. sports drinks).
  • the present disclosure provides a convenient water-soluble composition of cannabinoids and/or terpenes that may be used in beverages, foodstuffs and other recreational and/or medicinal products. More particularly, in select embodiments, the present disclosure provides a composition of cannabinoids and/or terpenes for use in liquid or powder forms that is soluble in water, and capable of improving the dispersibility and stability of cannabinoids to provide for acceptable shelf-life and consumer appeal (e.g. lack of sediment, homogeneous appearance, etc.) of the products produced therefrom, such as for example beverages. Most suitably, and in select embodiments, the water-soluble compositions are physically and chemically stable.
  • the present disclosure is directed to such cannabinoid and/or terpene compositions for use in beverages, foods and other products, and to methods of preparing the compositions.
  • the present disclosure is also directed to foodstuffs and beverages comprising said compositions (e.g. produced using the compositions of the present disclosure).
  • the present disclosure relates to a composition comprising: at least one cannabinoid and/or terpene; at least one saccharide; at least one surfactant; and at least one carrier oil.
  • the present disclosure is also directed to methods of preparing the compositions that are commercially-viable, efficient, and capable of producing shelf-stable products, such as beverages and foodstuffs.
  • the present disclosure is also directed to a beverage or foodstuff comprising the composition of the present disclosure.
  • compositions of the present disclosure may improve the ability to formulate cannabinoids and/or terpenes into aqueous mediums (e.g. beverages and foodstuffs), and in particular sports drink beverages.
  • aqueous mediums e.g. beverages and foodstuffs
  • sports drink beverages e.g. sports drink beverages
  • FIG. 1 depicts a particle size distribution graph of an exemplary composition (Composition 1).
  • FIG. 2 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 2).
  • FIG. 3 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 3).
  • FIG. 4 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 4).
  • FIG. 5 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 5).
  • FIG. 6 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 6).
  • FIG. 7 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 7).
  • FIG. 8 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 8).
  • FIG. 9 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 9).
  • FIG. 10 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 10).
  • FIG. 11 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 11).
  • FIG. 12 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 12).
  • FIG. 13 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 13).
  • FIG. 14 depicts a particle size distribution graph of an exemplary composition (Composition 14).
  • the present disclosure is generally directed to water-soluble cannabinoid and/or terpene compositions, methods for their preparation, and use thereof.
  • the compositions are suitably in a nontoxic consumable liquid form or a dispersible powder form.
  • the compositions may also be absorbed, sprayed or otherwise applied into or onto a solid material (e.g. a tea bag).
  • a solid material e.g. a tea bag.
  • embodiments of the compositions disclosed herein provide stability, solubility in water, have minimal flavour and odor, and are natural in origin.
  • compositions of the present disclosure include a cannabinoid and/or a terpene, and in particular, may include a cannabinoid distillate and/or a cannabinoid isolate.
  • Cannabis has been used in beverage preparations for years. Most of the historical cannabis beverages were prepared by boiling or grinding cannabis leaves, combining with water, milk, alcohol, or another biocompatible matrix or beverage liquid and, optionally, mixing with herbal or other plant-based compositions to form the final consumable.
  • the present disclosure provides improved compositions for cannabinoids.
  • the compositions of the present disclosure comprising at least one cannabinoid, at least one saccharide, at least one surfactant, and at least one carrier oil are highly soluble/dispersible in aqueous mediums (e.g. Example 1 ).
  • Sports drink beverages may present unique formulation challenges for cannabinoids due to the presence of salts (e.g. electrolytes), flavours or other components that may impact solubility, dispersibility, and/or stability.
  • salts e.g. electrolytes
  • flavours or other components that may impact solubility, dispersibility, and/or stability.
  • the water soluble compositions of the present disclosure were yet capable of preparing cannabinoid-infused sports drink beverages with desirable physical and chemical stability properties (e.g. Example 1 ).
  • the present disclosure provides convenient water- soluble compositions of cannabinoids that may be readily used in the preparation of beverages and foodstuffs.
  • compositions of the present disclosure comprise at least one cannabinoid and/or terpene, at least one saccharide, at least one surfactant, and at least one carrier oil.
  • cannabinoid e.g. a ratio of cannabinoid:surfactant
  • terpene(s) e.g. a ratio of cannabinoid:surfactant
  • composition is meant to refer broadly to any product or material comprised of two or more components (e.g. a cannabinoid and/or terpene, a saccharide, a surfactant and a carrier oil).
  • a “formulation” is meant to define the composition according to a particular physical state (e.g. powder or liquid) or the act, process or result of formulating according to a particular formula.
  • any features described for compositions of the present disclosure may also apply to formulations, and vice versa.
  • compositions herein serve as a convenient water-soluble dosage form of cannabinoids and/or terpenes for use in beverages, topicals and foodstuffs.
  • the compositions are suitably in a nontoxic consumable liquid or solid form.
  • water-soluble has its ordinary meaning in referring to the ability of a composition or component thereof to dissolve when the object is placed in water. For example, when the object is mixed with water at room temperature or slightly above (e.g. about 25°C to about 50°C).
  • the components of the compositions disclosed herein are at particular ratios to one another.
  • the particular ratio of components present in the compositions of the present disclosure may improve the ability to formulate cannabinoids into aqueous mediums (e.g. beverages and foodstuffs) to provide a desirable product.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of cannabinoid:surfactant of between 50:1 and 1 :50, between 25:1 and 1 :25, between 10:1 and 1 :10, between 9:1 and 1 :9, between 8:1 and 1 :8, between 7:1 and 1:7, between 6:1 and 1 :6, between 5:1 and 1 :5, between 4:1 and 1 :4, between 3:1 and 1 :3, or between 2:1 and 1 :2 by weight.
  • cannabinoid:surfactant of between 50:1 and 1 :50, between 25:1 and 1 :25, between 10:1 and 1 :10, between 9:1 and 1 :9, between 8:1 and 1 :8, between 7:1 and 1:7, between 6:1 and 1 :6, between 5:1 and 1 :5, between 4:1 and 1 :4, between 3:1 and 1 :3, or between 2:1 and 1 :2 by weight.
  • the ratio of cannabinoid:surfactant may be between 10:1 and 1 :5, between 5:1 and 1 :2.5, or between 2.5:1 and 1 :2.5 by weight. In an embodiment, the ratio of cannabinoid:surfactant may be about 10:1 , about 9:1 , about 8:1, about 7:1 , about 6:1 , about 5:1 , about 4:1 , about 3:1 , about 2:1 , about 1 :1 , about 1 :1.5, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of cannabinoid:carrier oil of between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight.
  • the ratio of cannabinoid:carrier oil may be between 1:1 and 1:2 by weight.
  • the ratio of cannabinoid:carrier oil may be about 10:1, about 9:1, about 8:1, about 7:1 , about 6:1, about 5:1 , about 4:1, about 3:1 , about 2:1, about 1:1, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of cannabinoid:saccharide of between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1 :2 by weight.
  • the ratio of cannabinoid:saccharide may be between 1:1 and 1:25, between 1:2 and 1:15, or between 1:5 and 1:10 by weight.
  • the ratio of cannabinoid:saccharide may be about 10:1, about 9:1, about 8:1, about 7:1, about 6:1 , about 5:1, about 4:1 , about 3:1, about 2:1 , about 1:1, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, about 1:10, about 1:11, about 1:12, about 1:13, about 1:14, about 1:15, about 1:16, about 1:17, about 1:18, about 1:19, about 1 :20, about 1 :21 , about 1 :22, about 1 :23, about 1 :24, or about 1 :25 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide:surfactant of between 100:1 and 1:100, between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1 :3, or between 2:1 and 1 :2 by weight.
  • the ratio of saccharide:surfactant may be between 50:1 and 1:1, between 45:1 and 1:1, between 40:1 and 1:1, between 35:1 and 1:1, between 35:1 and 2:1, or between 35:1 and 3:1 by weight. In an embodiment, the ratio of saccharide:surfactant may be between 40:1 and 1:2 by weight.
  • the ratio of saccharide:surfactant may be about 100:1, about 75:1, about 50:1 , about 45:1, about 40: 1 , about 35: 1 , about 30: 1 , about 25: 1 , about 20: 1 , about 15:1, about 14:1, about 13:1, about 12:1, about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1, about 5:1 , about 4.5:1, about 4:1 , about 3.5:1, about 3:1, about 2.5:1, about 2:1, about 1.5:1, about 1:1, about 1:2, about 1:3, about 1:4, or about 1:5 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide:carrier oil of between 50:1 and 1:50, between 25:1 and 1:25, between 15:1 and 1:1, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight.
  • the ratio of saccharide:carrier oil may be between 15:1 and 1:1, between 14:1 and 1:1, between 13:1 and 1:1, between 12:1 and 1:1, between 11:1 and 1:1, between 10:1 and 1:1, between 9:1 and 1:1, between 8:1 and 7:1, between 6:1 and 1:1, between 5:1 and 1:1, between 4:1 and 1:1, between 3:1 and 1:1, or between 2:1 and 1:1 by weight.
  • the ratio of saccharide:carrier oil may be about 25:1, about 20:1, about 15:1 , about 14:1, about 13:1, about 12:1, about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1, about 5:1, about 4.5:1 , about 4:1, about 3.5:1, about 3:1, about 2.5:1, about 2:1, about 1.5:1, about 1:1, about 1:2, about 1:3, about 1 :4, or about 1 :5 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of carrier oiksurfactant of between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight.
  • the ratio of carrier oiksurfactant may be between 10:1 and 1:5, between 5:1 and 1:2.5, or between 2.5:1 and 1:2.5 by weight.
  • the ratio of carrier oiksurfactant may be between 15:1 and 1:5, and more particularly between 12:1 and 1 :2 by weight. In an embodiment, the ratio of carrier oiksurfactant may be about 15:1 , about 14:1, about 13:1, about 12:1 , about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1 , about 5:1, about 4:1 , about 3:1, about 2:1 , about 1:1, about 1:1.5, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight. [0048] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5-2 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight.
  • compositions of the present disclosure and/or products produced therefrom may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, THCVA, CBD, CBD
  • glyceryl monostearate glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CO, PeceolTM), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of cannabinoid:saccharide of between 50:1 and 1 :50, and/or a ratio of saccharide:surfactant of between 100:1 and 1 :100, and/or a ratio of saccharide:carrier oil of between 50:1 and 1 :50 by weight.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, THCVA, CBD, CBD
  • glyceryl monostearate glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CO, PeceolTM), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight.
  • the composition has a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5- 2 : 1 by weight.
  • the ratio of saccharide : carrier oil : surfactant may be any ratio within the disclosed ranges.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, THCVA, CBD, CBD
  • glyceryl monostearate glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, PeceolTM), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight.
  • the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight.
  • the ratio of saccharide : cannabinoid : carrier oil : surfactant may be any ratio within the disclosed ranges.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from THC (A9-TH
  • composition has a ratio of cannabinoid:saccharide of between 50:1 and 1 :50, and/or a ratio of saccharide:surfactant of between 100:1 and 1 :100, and/or a ratio of saccharide:carrier oil of between 50:1 and 1 :50.
  • the ratio of cannabinoid:saccharide, saccharide:surfactant and saccharide:carrier oil may be any ratio within the disclosed ranges, and in some embodiments may be the ratios disclosed elsewhere herein.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from THC (A9-TH
  • the composition has a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight.
  • the composition has a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight.
  • the composition has a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight.
  • the composition has a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5- 2 : 1 by weight.
  • the ratio of saccharide : carrier oil : surfactant may be any ratio within the disclosed ranges.
  • the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from THC (A9-TH
  • composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight.
  • the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight.
  • the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight.
  • the ratio of saccharide : cannabinoid : carrier oil : surfactant may be any ratio within the disclosed ranges.
  • the water-soluble compositions, dosage forms, beverages or foodstuffs of the present disclosure may provide fast onset of biological effects of the cannabinoids in human or animal consumers or subjects.
  • the compositions of the present disclosure may provide advantageous properties for formulating products (e.g. beverages and foodstuffs) which are capable of by-passing first pass metabolism and thereby improving bioavailability of cannabinoids.
  • compositions of the present disclosure comprise at least one cannabinoid.
  • the compositions may comprise a single cannabinoid (e.g. THC, CBD or another cannabinoid) or may comprise any combination of two or more cannabinoids (e.g. CBD and THC).
  • the compositions may also comprise at least one terpene in combination with the at least one cannabinoid.
  • cannabinoid refers to a compound belonging to a class of secondary compounds commonly found in plants of genus cannabis, but also encompasses synthetic and semi-synthetic cannabinoids.
  • a cannabinoid is one of a class of diverse chemical compounds that acts on cannabinoid receptors such as CB1 and CB2 in cells that alter neurotransmitter release in the brain.
  • cannabinoids of the phytocannabinoids is tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis.
  • Cannabidiol (CBD) is another cannabinoid that is a major constituent of the plant. There are at least 113 different cannabinoids isolated from cannabis, exhibiting varied effects.
  • the cannabinoid is a compound found in a plant, e.g., a plant of genus cannabis, and is sometimes referred to as a phytocannabinoid.
  • the cannabinoid is a compound found in a mammal, sometimes called an endocannabinoid.
  • the cannabinoid is made in a laboratory setting, sometimes called a synthetic cannabinoid.
  • the cannabinoid is derived or obtained from a natural source (e.g. plant) but is subsequently modified or derivatized in one or more different ways in a laboratory setting, sometimes called a semi-synthetic cannabinoid.
  • Synthetic cannabinoids and semisynthetic cannabinoids encompass a variety of distinct chemical classes, for example and without limitation: the classical cannabinoids structurally related to THC, the non-classical cannabinoids (cannabimimetics) including the aminoalkylindoles, 1 ,5-diarylpyrazoles, quinolines, and arylsulfonamides as well as eicosanoids related to endocannabinoids.
  • a cannabinoid can be identified because its chemical name will include the text string “*cannabi*”.
  • cannabinoids that do not use this nomenclature, such as for example those described herein.
  • each of the acid and/or decarboxylated forms are contemplated as both single molecules and mixtures.
  • salts of cannabinoids are also encompassed, such as salts of cannabinoid carboxylic acids.
  • any and all isomeric, enantiomeric, or optically active derivatives are also encompassed.
  • reference to a particular cannabinoid incudes both the “A Form” and the “B Form”.
  • THCA has two isomers, THCA-A in which the carboxylic acid group is in the 1 position between the hydroxyl group and the carbon chain (A Form) and THCA-B in which the carboxylic acid group is in the 3 position following the carbon chain (B Form).
  • cannabinoids include, but are not limited to, Cannabigerolic Acid (CBGA), Cannabigerolic Acid monomethylether (CBGAM), Cannabigerol (CBG), Cannabigerol monomethylether (CBGM), Cannabigerovarinic Acid (CBGVA), Cannabigerovarin (CBGV), Cannabichromenic Acid (CBCA), Cannabichromene (CBC), Cannabichromevarinic Acid (CBCVA), Cannabichromevarin (CBCV), Cannabidiolic Acid (CBDA), Cannabidiol (CBD), A6-Cannabidiol (A6-CBD), Cannabidiol monomethylether (CBDM), Cannabidiol-C4 (CBD-C4), Cannabidivarinic Acid (CBDVA), Cannabidivarin (CBDV), Cannabidiorcol (CBD-C1), Tetrahydrocannabinolic Acid (CBGA
  • the cannabinoid is a cannabinoid dimer.
  • the cannabinoid may be a dimer of the same cannabinoid (e.g. THC — THC) or different cannabinoids.
  • the cannabinoid may be a dimer of THC, including for example cannabisol.
  • THC refers to tetrahydrocannabinol. “THC” refers to and is used interchangeably herein with “A9-THC”.
  • the at least one cannabinoid is THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, cannabicitran, or any acid form thereof, or any combination of any of the foregoing.
  • Structural formulae of cannabinoids of the present disclosure may include the following: cannabicitran
  • the at least one cannabinoid is THC, CBD, CBN, CBG, CBGA, or any combination thereof.
  • the at least one cannabinoid is THC (A9-THC), A8-THC, trans-M 0-THC, c/s-A10-THC, THCV, A8-THCV, A9-THCV, CBD, CBDV, CBC, CBG, CBL, CBN, CBT, or any acid form thereof, or any combination of any of the foregoing.
  • the at least one cannabinoid is THC, CBD, or a combination thereof.
  • the at least one cannabinoid is THC.
  • the at least one cannabinoid is CBD.
  • the at least one cannabinoid comprises more than one cannabinoid, and in particular, a combination of THC and CBD.
  • the at least one cannabinoid may be introduced in the form of a pure or purified cannabinoid.
  • purified or “pure” means extracted, isolated, and/or separated from other compounds, formulations, compositions, matter, and/or mass resulting in a greater than 60% purity.
  • a non-limiting example of a purified cannabinoid is a cannabinoid isolate.
  • a “purified” cannabinoid is greater than about 70% pure, greater than about 75% pure, greater than about 80% pure, greater than about 85% pure, greater than about 90% pure, greater than about 91% pure, greater than about 92% pure, greater than about 93% pure, greater than about 94% pure, greater than about 95% pure, greater than about 96% pure, greater than about 97% pure, greater than about 98% pure, or greater than about 99% pure.
  • the term “purified” includes enantiomerically pure compositions and also mixtures of enantiomers or isomers.
  • purified compounds may be purposely formulated with other compounds at various levels of purity. Provided that the ingredients used for purposeful formulation are purified prior to the said purposeful formulation, the act of subsequently formulating them does render them not “purified” within the context of an ingredient list.
  • the term “purified” may refer to a cannabinoid that is separated from plant matter from which it was derived.
  • the pure or purified cannabinoid may be contained in solution in a diluent or other medium, or may be a liquid or solid form of the pure cannabinoid absent any diluent.
  • the at least one cannabinoid may be a synthetic or semi-synthetic cannabinoid.
  • the at least one cannabinoid may be introduced in the form of a cannabis concentrate.
  • “cannabis concentrate” is meant to refer a concentrated composition of cannabinoids, such as a cannabinoid extract from a plant.
  • Non-limiting exemplary embodiments of a cannabis concentrate include a full spectrum extract, a broad spectrum extract, a cannabis distillate, a cannabis oil, or any other type of extract containing one or more cannabinoids.
  • the cannabis concentrate is a cannabis distillate.
  • the compositions may include up to about 35% by weight cannabinoid, more particularly up to about 25% by weight cannabinoid, and more particularly still up to about 15% by weight cannabinoid. In select embodiments, the compositions may include between about 0.1% and about 25% by weight cannabinoid. In an embodiment, the compositions may include between about 5% and about 15% by weight, and more particularly between about 10% and about 15% by weight cannabinoid.
  • the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight of cannabinoid.
  • compositions of the present disclosure comprise at least one terpene.
  • the compositions may comprise a single cannabinoid (e.g. beta-caryophyllene or another terpene) or may comprise any combination of two or more cannabinoids (e.g. beta-caryophyllene and linalool).
  • the compositions may also comprise at least one cannabinoid in combination with the at least one cannabinoid.
  • the term “terpene” includes cannabis derived terpenes and non-cannabis derived terpenes. Within the context of this disclosure, the term “terpene” also includes terpeoinds. Thus, the reference to “at least one terpene” encompasses and means “at least one terpene and/or terpenoid”. In an embodiment, the compositions herein may comprise at least one terpene and/or terpenoid. In an embodiment, the product containing the compositions herein may comprise at least one terpene and/or terpenoid.
  • Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, and by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeteria. Terpenes are also major constituents of Cannabis sativa plants. They often have a strong odor and may protect the plants that produce them by deterring herbivores and by attracting predators and parasites of herbivores. The difference between terpenes and terpenoids is that terpenes are hydrocarbons, whereas terpenoids contain additional functional groups.
  • terpenes are major biosynthetic building blocks within nearly every living creature. Steroids, for example, are derivatives of the triterpene squalene.
  • terpenoids When terpenes are modified chemically, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Some authors will use the term terpene to include all terpenoids. Terpenoids are also known as isoprenoids.
  • terpene includes hemiterpenes, monoterpenols, terpene esters, diterpenes, monoterpenes, polyterpenes, tetraterpenes, terpenoid oxides, sesterterpenes, sesquiterpenes, norisoprenoids, or their derivatives, as well as isomeric, enantiomeric, or optically active derivatives.
  • terpenes include terpenoids, hemiterpenoids, monoterpenoids, sesquiterpenoids, sesterterpenoid, sesquarterpenoids, tetraterpenoids, triterpenoids, tetraterpenoids, polyterpenoids, isoprenoids, and steroids. These derivatives are encompassed herein by the term “terpene”, unless specifically stated otherwise.
  • terpene includes the a- (alpha), p- (beta), y- (gamma), oxo-, isomers, or any combinations thereof.
  • Terpenes are the primary constituents of the essential oils of many types of plants and flowers.
  • Essential oils are used widely as fragrances in perfumery, and in medicine and alternative medicines such as aromatherapy.
  • Synthetic variations and derivatives of natural terpenes also greatly expand the variety of aromas used in perfumery and flavours used in food additives.
  • compositions of the present disclosure may include hop-derived terpenes such as hop-derived terpene blends available as Aramis, Brewer's Gold, Bravo and the like, and combinations thereof.
  • Plant terpenes are used extensively for their aromatic qualities and play a role in traditional herbal remedies. Terpenes contribute to the scent of eucalyptus, the flavours of cinnamon, cloves, and ginger, the yellow colour in sunflowers, and the red colour in tomatoes.
  • Non-limiting examples of terpenes within the context of this disclosure include: 7,8-dihydro-alpha-ionone, 7,8-dihydro-beta-ionone, Acetanisole, Acetic Acid, Acetyl Cedrene, Anethole, Anisole, Benzaldehyde, Bergamotene (Alpha-cis-Bergamotene) (Alpha- trans-Bergamotene), Bisabolol (Beta-Bisabolol), Alpha Bisabolol, Borneol, Bornyl Acetate, Butanoic/ Butyric Acid, Cadinene (Alpha-Cadinene) (Gamma-Cadinene), cafestol, Caffeic acid, Camphene, Camphor, Capsaicin, Carene (Delta-3-Carene), Carotene, Carvacrol, Dextro-Carvone, Laevo-Carvone, Alpha-
  • compositions disclosed herein comprise a terpene selected from p-caryophyllene, caryophyllene oxide, borneol, 1 ,8-cineole, camphene, humulene (e.g., a-humulene), limonene (e.g., D-limonene, L-limonene), linalool, hexyl acetate, myrcene (e.g., 3-myrcene), nerolidol, pulegone, isopulegol, a-pinene, 3-pinene, para-cymene, eugenol, farnesol, geraniol, phytol, terpinene (e.g., gammaterpinene), terpineol (e.g., a-terpineol) and terpinolene, or any combination thereof.
  • humulene e.g., a-hum
  • compositions disclosed herein comprise p-caryophyllene as at least one of the terpenes.
  • each of the at least one terpenes have a particle size diluted in water of between about 100 nm and about 110 nm, with a polydispersity of 0.1 or less.
  • the compositions include terpenes and/or terpenoids having antimicrobial properties.
  • exemplary antimicrobial terpenes include, for example, Ocimum basilicum (basil), Laurus nobilis (bay), Cinnamomum verum (Ceylon cinnamon), Capsicum annuum (paprika), Syzygium aromaticum (clove), Mentha piperita (peppermint), Tanacetum vulgare (tansy), Artemisia dracunculus (Tarragon), and the like as known in the art.
  • the at least one terpene may be introduced in the form of a pure or purified terpene.
  • purified or “pure” means extracted, isolated, and/or separated from other compounds, formulations, compositions, matter, and/or mass resulting in a greater than 60% purity.
  • a non-limiting example of a purified terpene is a terpene isolate.
  • a “purified” terpene is greater than about 70% pure, greater than about 75% pure, greater than about 80% pure, greater than about 85% pure, greater than about 90% pure, greater than about 91% pure, greater than about 92% pure, greater than about 93% pure, greater than about 94% pure, greater than about 95% pure, greater than about 96% pure, greater than about 97% pure, greater than about 98% pure, or greater than about 99% pure.
  • the term “purified” includes enantiomerically pure compositions and also mixtures of enantiomers or isomers.
  • the term “purified” may refer to a terpene that is separated from plant matter from which it was derived.
  • the pure or purified terpene may be contained in solution in a diluent or other medium, or may be a liquid or solid form of the pure terpene absent any diluent.
  • the at least one terpene may be a synthetic or semi-synthetic terpene.
  • the at least one terpene may be introduced in the form of a terpene concentrate.
  • terpene concentrate is meant to refer a concentrated composition of terpenes, such as a terpene extract from a plant.
  • Non-limiting exemplary embodiments of a terpene concentrate include a terpene distillate, a terpene oil, or any other type of extract containing one or more terpenes.
  • the terpene concentrate is a terpene distillate.
  • the compositions may include up to about 35% by weight , more particularly up to about 25% by weight terpene, and more particularly still up to about 15% by weight terpene. In select embodiments, the compositions may include between about 0.1% and about 25% by weight terpene. In an embodiment, the compositions may include between about 5% and about 15% by weight, and more particularly between about 10% and about 15% by weight terpene.
  • the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight of terpene.
  • the compositions may include a total terpene concentration (relative to the concentration of cannabinoids) beyond what would normally be found in the cannabis flower, allowing for the potential of entourage effects.
  • the “entourage-effect” refers to the residual effect of one or more compounds (e.g., cannabinoids, terpenes) of the compositions in the ultimately administered end products.
  • compositions of the present disclosure may also include additives, such as for example flavonoids, encapsulation materials, and the like and combinations thereof.
  • additives e.g. flavonoids and/or encapsulation materials
  • the additives are independently or in combination derived from natural sources and are selected to be stable in the selected compositions, dosage forms, beverages or foodstuffs herein.
  • compositions disclosed herein comprise at least one saccharide.
  • the at least one saccharide may be a naturally occurring saccharide, a synthetic saccharide, or a combination thereof.
  • the saccharide is a carbohydrate.
  • carbohydrate refers to a compound consisting of carbon, hydrogen, and oxygen atoms.
  • the carbohydrate has the formula C n H2nO n , wherein n is an integer.
  • the saccharide may be a modified carbohydrate that includes one or more atoms other than carbon, hydrogen, and oxygen.
  • the saccharide may be a monosaccharide, a disaccharide, oligosaccharide, a polysaccharide, or any combination thereof. While a disaccharide contains two monosaccharide units, there is overlap between an oligosaccharide and a polysaccharide.
  • An oligosaccharide is typically considered to contain a small number of monosaccharide units (e.g. 2-20 units, and more particularly 3-10 units), whereas a polysaccharide is typically considered to contain a large number of monosaccharide units, for example more than twenty and often hundreds.
  • the saccharide is a monosaccharide.
  • Monosaccharides are classified by the number of carbon atoms they contain (e.g. triose (3), tetrose (4), pentose (5), hexose (6), and so on).
  • Non-limiting examples of monosaccharides include glucose (dextrose), fructose, galactose, xylose, ribose, and inositol (e.g. myo-inositol).
  • the monosaccharide is inositol.
  • the monosaccharide is myo-inositol.
  • Myo-inositol, or (1R,2S,3R,4R,5S,6s)-cyclohexane- 1 ,2,3,4,5,6-hexol is a sugar alcohol that can also be made naturally in humans from glucose.
  • the saccharide is a disaccharide.
  • disaccharides include sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, and chitobiose.
  • the saccharide is an oligosaccharide.
  • oligosaccharides include raffinose, stachyose, and verbascose.
  • Various classes of oligosaccharides exist, including without limitation, fructooligosaccharides and galactoooligosaccharides.
  • the saccharide is a polysaccharide.
  • polysaccharides include inulin, pectin, amylopectin, beta-glucan, glycogen, and maltodextrin.
  • the at least one saccharide is glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta glucan, glycogen, maltodextrin, or any combination thereof.
  • the at least one saccharide is inulin.
  • Inulin (C6nHi0n+2O5n+i) is a heterogeneous mixture of fructose polymers typically extracted from chicory.
  • Other exemplary natural sources of inulin include asparagus, garlic, artichoke, jicama, onions, and yacon root.
  • Inulin consists of a chain-terminating glucose moiety and repetitive fructosyl moieties, which are linked by p-(2 ⁇ >1 ) bonds.
  • the degree of polymerization for inulin ranges from 2-60. Inulin may be obtained from any number of plant sources, and may also be modified or manufactured.
  • Oligofructose is a subgroup of inulin made by removing the longer molecules.
  • oiligofructose comprises fructose molecules of between two to ten units.
  • High-performance (HP) inulin is a subgroup of inulin made by removing the shorter molecules.
  • HP inulin comprises fructose molecules of between 11 to 60 units, with an average degree of polymerization typically around 25.
  • Fructooligosaccharides are a subgroup of inulin consisting of short inulin molecules synthesized from table sugar.
  • the at least one saccharide is inositol.
  • the at least one saccharide is myo-inositol. [00128] In another embodiment, the at least one saccharide is a combination of inositol and inulin. In another embodiment, the at least one saccharide is a combination of myo-inositol and inulin.
  • saccharide may also refer to a number of naturally occurring or synthetic compounds that are saccharide derivatives, such as saccharide substitutes.
  • saccharide substitutes may include sorbitol, stevia, mannitol, aspartame, sucralose, isomalt, and xylitol.
  • a combination of saccharides may be used in the compositions disclosed herein. When more than one saccharide is used, they may be used at any amount relative to the other.
  • the first saccharide and the second saccharide may be used at a ratio between 20:1 and 1 :20, between 15:1 and 1 :15, between 10:1 and 1 :10, or between 5:1 and 1 :5 by weight to each other.
  • the two saccharides may be used at about a 4:1 , 3:1 , 2:1 , 1 :1 , 1 :2, 1 :3 or 1 :4 by weight ratio to each other.
  • the two saccharides may be used at about a 1 :1 by weight ratio to each other.
  • the compositions may include up to about 85% by weight saccharide, more particularly up to about 75% by weight saccharide, and more particularly still up to about 60% by weight saccharide. In select embodiments, the compositions may include between about 25% and about 85% by weight saccharide. In an embodiment, the compositions may include between about 35% and about 75% by weight, more particularly between about 50% and about 70% by weight, and more particularly still between about 55% and about 65% by weight saccharide. In select embodiments, the compositions may include about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, or about 70% by weight saccharide.
  • compositions herein comprise at least one surfactant.
  • the surfactant is a non-ionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, or any combination thereof.
  • the surfactant may be a natural surfactant.
  • the term “natural surfactant” is intended to refer to a surfactant obtained from a natural source.
  • non-ionic surfactant typically refers to a surfactant without an electrical charge.
  • Non-limiting examples of non-ionic surfactants include partial fatty acid esters, fatty alcohols, sterols, polyethylene glycols, such as ethoxylated fatty acids, ethoxylated fatty alcohols, and ethoxylated sorbitan esters, sugar emulsifiers, polyglycerol emulsifiers, and silicon emulsifiers.
  • anionic surfactant typically refers to a surfactant having a negative charge at the hydrophilic end.
  • anionic surfactants include soaps, such as sodium stearate, fatty alcohol sulfates, mono, di- and tri-alkyl phosphoric acid esters and the ethoxylates thereof, fatty acid lactate esters, fatty acid citrate esters, and fatty acid citroglycerin esters.
  • cationic surfactant typically refers to a surfactant having a positive charge.
  • Non-limiting examples of cationic surfactants include quaternary ammonium compounds having a long-chain aliphatic group, such as distearyldimonium chloride.
  • amphoteric surfactant typically refers to a surfactant having both an anionic and a cationic hydrophilic group (i.e. both a negative and a positive charge).
  • amphoteric surfactants include alkylamininoalkane carboxylic acids, betaines, sulfobetaines, and imidazoline derivatives.
  • the non-ionic surfactant may be a partial fatty acid ester, a fatty acid ester of glycerol (e.g. glycerol monostearate, glycerol monolaurate), a fatty alcohol, a sterol, a polyethylene glycol, an ethoxylated fatty acid (e.g. oleic acid ethoxylate, stearic acid ethoxylate, coconut fatty acid ethoxylate, lauric acid ethoxylate, and myristic/palmitic acid ethoxylate), an ethoxylated fatty alcohol (e.g.
  • octaethylene glycol monododecyl ether pentaethylene glycol monododecyl ether
  • a sorbitan ester an ethoxylated sorbitan ester, an ethoxylated amines or fatty acid amide (e.g. polyethoxylated tallow amine, cocamide monoethanolamine, and cocamide diethanolamine), a polyglycerol, a polglyceryl ester (monoester and multi-ester), or any combination thereof.
  • Non-limiting examples of sorbitan esters include Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, or any combination thereof.
  • the surfactant may be an ethoxylated sorbitan ester, such as for example Tween 20, Tween 40, Tween 45, Tween 60, Tween 65, Tween 80, Tween 81 , Tween 85, or any combination thereof.
  • Non-limiting examples of polyglyceryl esters include Polyglyceryl-4 Caprate, Polyglyceryl-4 Caprylate, Polyglyceryl-4 Isostearate, Polyglyceryl-4 Laurate, Polyglyceryl-4, Oleate, Polyglyceryl-5 Dioleate, Polyglyceryl-5 Isostearate, Polyglyceryl-5 Laurate, Polyglyceryl-5 Myristate, Polyglyceryl-5 Oleate, Polyglyceryl-5 Stearate, Polyglyceryl-5 Triisostearate, Polyglyceryl-5 Trioleate, Polyglyceryl-6 Dioleate, Polyglyceryl-6 Distearate, Polyglyceryl-6 Isostearate, Polyglyceryl-6 Octastearate, Polyglyceryl-6 Oleate, Polyglyceryl- 6 Pentastearate, Polyglyceryl-6 Stearate, Polyglyceryl-6 Tricaprylate, Polyglyceryl-8 Decaeru
  • the anionic surfactant may be sodium stearate, an alkyl sulfate (e.g. ammonium lauryl sulfate, sodium lauryl sulfate, sodium dodecyl sulfate), an alkyl-ether sulfate (e.g. sodium lauryl ether sulfate, Sodium myreth sulfate), a fatty alcohol sulfate, a mono, di- and tri-alkyl phosphoric acid ester or an ethoxylate thereof, a fatty acid lactate ester, a fatty acid citrate ester, a fatty acid citro-glycerin ester, or any combination thereof.
  • an alkyl sulfate e.g. ammonium lauryl sulfate, sodium lauryl sulfate, sodium dodecyl sulfate
  • an alkyl-ether sulfate e.g. sodium lauryl ether
  • the cationic surfactant may be a quaternary ammonium compound having a long-chain aliphatic group (e.g. cetrimonium bromide, cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, dimethyldioctadecylammonium chloride, dioctadecyldimethylammonium bromide, or any combination thereof.
  • cetrimonium bromide cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, dimethyldioctadecylammonium chloride, dioctadecyldimethylammonium bromide, or any combination thereof.
  • the amphoteric surfactant may be an alkylamininoalkane carboxylic acid, a betaine (e.g. cocamidopropyl betaine), a sulfobetaine, or an imidazoline derivative.
  • the at least one surfactant comprises a natural surfactant.
  • natural surfactants include, without limitation, surfactants comprising saponins, a lecithin, gum arabic, or a sterol.
  • Saponins are naturally occurring compounds that are found in a wide variety of plants (e.g. legumes), and are also produced by some lower marine animals and some bacteria.
  • the surfactant may comprise saponins from any suitable source.
  • the saponins may be from Quillaja, Soapwort (Saponaria), Quinoa (Chenopodium), Soap nut (Sapindus), Soapweed (Yucca), Soapbush (Alphitonia), Soaproot (Chlorogallum), Buffaloberry (Shepherdia), or any combination thereof.
  • the surfactant comprises Quillaja saponins.
  • the surfactant comprising Quillaja saponins may be from any suitable source.
  • Quillaja saponins may be derived from a Quillaja tree, such as for example a Quillaja saponaria tree or a Quillaja brasiliensis tree.
  • the surfactant comprising Quillaja saponins is derived from a Quillaja saponaria tree.
  • the surfactant comprising Quillaja saponins is a Q-NATURALE® surfactant (Ingredion Incorporated, USA), a Saponin from Quallaja Bark (such as for example supplied by Sigma Aldrich, USA), Saponin Quillaja sp. (Sigma Aldrich, USA), a Quillaja extract (such as for example Quillaja extract E 999;), purified Quillaja saponins (e.g. from Sigma Aldrich, USA), a modified Quillaja extract, or combinations thereof.
  • Q-NATURALE® surfactant Ingredion Incorporated, USA
  • a Saponin from Quallaja Bark such as for example supplied by Sigma Aldrich, USA
  • Saponin Quillaja sp. Sigma Aldrich, USA
  • a Quillaja extract such as for example Quillaja extract E 999;
  • purified Quillaja saponins e.g. from Sigma Aldrich, USA
  • the surfactant comprising Quillaja saponins is a Q-NATURALE® surfactant.
  • the Q-NATURALE® surfactant comprises Q-NATURALE® 200, Q-NATURALE® 200V, or a combination thereof.
  • the Q-NATURALE® surfactant is Q-NATURALE® 200.
  • Q-NATURALE® 200 is described as a natural emulsifier extracted from Quillaja trees and comprising about 65-75% saponin (dry basis) (Ingredion Incorporated, USA). However, modifications and alterations to Q-NATURALE® 200 are also encompassed herein.
  • the Q-NATURALE® surfactant is Q-NATURALE® 200V.
  • Q-NATURALE® 200V is described as a naturally-derived liquid emulsifier derived from the Quillaja Saponaria Molina tree comprising about 13-16% Saponin (wet basis) (Ingredion Incorporated, USA). However, modifications and alterations to Q-NATURALE® 200V are also encompassed herein.
  • Lecithin is a term commonly used to describe a group of fatty acid substances found in plant and animal tissues.
  • exemplary sources of lecithin include, without limitation, lecithin which is found in egg-yolks and milk, as well as being extracted from soy beans (i.e. soy lecithin), sunflower (i.e. sunflower lecithin), canola (i.e. canola lecithin), rapeseed (i.e. rapeseed lecithin), cottonseed (i.e. cottonseed lecithin), marine sources, and animal fats. Lysolecithins may also be used as a surfactant in the compositions disclosed herein.
  • lecithin Any type of lecithin may be used in the practice of the present disclosure.
  • the lecithin is a soy lecithin, sunflower lecithin, canola lecithin, rapeseed lecithin, cottonseed lecithin, or any combination thereof.
  • the lecithin is a soy lecithin.
  • the lecithin is a sunflower lecithin.
  • the lecithin is a purified lecithin such as, for example, Lipoid S 40, Lipoid H 50, Lipoid PHOSAL® 50 SA, Lipoid PHOSAL® 53 MCT, Lipoid P 75, Lipoid S 75, Lipoid S 80, Lipoid E 80, PHOSPHOLIPON® 85 G, Lipoid PHOSPHOLIPON® 90 G, Lipoid PHOSPHOLIPON® 90 H, Lipoid H 100, or any combination thereof.
  • a purified lecithin such as, for example, Lipoid S 40, Lipoid H 50, Lipoid PHOSAL® 50 SA, Lipoid PHOSAL® 53 MCT, Lipoid P 75, Lipoid S 75, Lipoid S 80, Lipoid E 80, PHOSPHOLIPON® 85 G, Lipoid PHOSPHOLIPON® 90 G, Lipoid
  • the lecithin is of the ALCOLEC® family of lecithins (e.g. ALCOLEC® F-100, ALCOLEC® EM, ALCOLEC® S, ALCOLEC® BS, ALCOLEC® HL, ALCOLEC® H 20, ALCOLEC® EXTRA-A, ALCOLEC® E 35, ALCOLEC® E 60 or ALCOLEC® HR), including deoiled soy lecithin.
  • ALCOLEC® family of lecithins e.g. ALCOLEC® F-100, ALCOLEC® EM, ALCOLEC® S, ALCOLEC® BS, ALCOLEC® HL, ALCOLEC® H 20, ALCOLEC® EXTRA-A, ALCOLEC® E 35, ALCOLEC® E 60 or ALCOLEC® HR
  • Sterol is an organic compound of the formula C17H28O. It contains the gonane structure with replacement of a hydrogen atom in position 3 with a hydroxyl group. Thus, it is an alcohol of gonane. Sterol occurs naturally in most eukaryotes, including plants, animals, and fungi. Sterol surfactant include, without limitation, sterol ethoxylates and sterol glucosides.
  • the surfactant may be a polyglyceryl surfactant, and/or a long chain PEG surfactant.
  • the surfactant may be glyceryl laurate, glyceryl stearate citrate, or derivatives thereof.
  • the surfactant may comprise polyglycol ized glycerides, polyoxyethylene glycerides, polyethylene glycol-fatty acid esters, polyethylene glycol glycerol fatty acid esters, transesterfication products of oils and alcohols, polyglycerized fatty acids, glycerol fatty acid esters, polyglycerol fatty acid esters, propylene glycol fatty acid esters, mono- and di-glycerides, polyethylene glycol sorbitan fatty acid esters, polyoxyethylene- polyoxypropylene block copolymers, sorbitan fatty acid esters, d-a-tocopheryl polyethylene glycol 1000 succinate, polyoxyethyleneglycol 660 12-hydroxystearate, polysorbates, or any combination thereof.
  • the surfactant may comprise almond oil PEG-6 esters, almond oil PEG-60 esters, apricot kernel oil PEG-6 esters, caprylic/capric triglycerides PEG-4 esters, caprylic/capric glycerides PEG-6 esters, caprylic/capric glycerides PEG-8 esters, castor oil PEG-50 esters, hydrogenated castor oil PEG-5 esters, hydrogenated castor oil PEG-7 esters, hydrogenated castor oil PEG-9 esters, corn oil PEG-6 esters, corn oil PEG-8 esters, corn glycerides PEG-60 esters, olive oil PEG-6 esters, hydrogenated palm/palm kernel oil PEG-6 esters, hydrogenated palm/palm kernel oil PEG-6 esters with palm kernel oil and PEG-6 and palm oil, palm kernel oil PEG-40 esters, peanut oil PEG-6 esters, glycerol esters of saturated C8-C18 fatty acids, glyceryl esters of
  • the at least one surfactant may be a Vitamin E TPGS (e.g. Vitamin E TPGS 200, Vitamin E TPGS 300, Vitamin E TPGS 400, Vitamin E TPGS 1000, Vitamin E TPGS 1500, Vitamin E TPGS 2000 and Vitamin E TPGS 4000), Gum Arabic, PURITY GUM® ULTRA, and other like compounds.
  • Vitamin E TPGS e.g. Vitamin E TPGS 200, Vitamin E TPGS 300, Vitamin E TPGS 400, Vitamin E TPGS 1000, Vitamin E TPGS 1500, Vitamin E TPGS 2000 and Vitamin E TPGS 4000
  • Gum Arabic e.g. Vitamin E TPGS 200, Vitamin E TPGS 300, Vitamin E TPGS 400, Vitamin E TPGS 1000, Vitamin E TPGS 1500, Vitamin E TPGS 2000 and Vitamin E TPGS 4000
  • Gum Arabic e.g. Vitamin E TPGS 200, Vitamin E TPGS 300, Vitamin E TPGS 400, Vitamin E TPGS 1000, Vitamin E TPGS 1500
  • the surfactant may be a surfactant sold under the trademark BrijTM or ECO BrijTM (Croda, UK).
  • the surfactant is Polyoxyethylene (10) cetyl ether (Ceteth-10; e.g. BrijTM C10), Polyoxyethylene (20) cetyl ether (Ceteth-20; e.g. BrijTM C20), Polyoxyethylene (20) Cetyl Stearyl Ether (Ceteareth-20; e.g. BrijTM CS20), Alkoxylated ether (lsoceteth-20; e.g. BrijTM IC20); Alkoxylated ether and Aqua (lsocetech-20; e.g.
  • BrijTM IC20-70 Ethoxylated Fatty Alcohol (Laureth-4; e.g. BrijTM L4), Polyoxyethylene (23) lauryl ether (Laureth-23; e.g. BrijTM L23), Polyoxyethylene (23) lauryl ether and Aqua (Laureth-23; e.g. BrijTM L23-69), Polyoxyethylene (10) oleyl ether (Oleth-10; e.g., BrijTM O10), Polyoxyethylene (20) oleyl ether (Oleth-20; e.g. BrijTM 020), Polyoxyethylene (10) stearyl ether (Steareth-10; e.g.
  • BrijTM S10 Polyoxyethylene (20) stearyl ether (Steareth-20; e.g. BrijTM S20), Polyoxyethylene (100) stearyl ether (Steareth- 100; e.g. BrijTM S100), ethoxylated fatty alcohols (Steareth-21 ; e.g. BrijTM S721 ), or any combination thereof.
  • ECO BrijTM Cosmetic BrijTM
  • DEG Polyoxyethylene
  • the compositions of the present disclosure may comprise a sucrose monoester as a surfactant, alone or in combination with other surfactants.
  • the sucrose monoester may be sucrose monopalmitate, sucrose monolaurate, sucrose monostearate, or any combination thereof.
  • the sucrose monoester may comprise a small quantity of diester.
  • a combination of surfactants may be used in the compositions disclosed herein. When more than one surfactant is used, they may be used at any amount relative to the other.
  • the first surfactant and the second surfactant may be used at a ratio between 20:1 and 1 :20, between 15:1 and 1 :15, between 10:1 and 1 :10, or between 5:1 and 1 :5 by weight to each other.
  • the two surfactants may be used at about a 4:1 , 3:1 , 2:1 , 1 :1 , 1 :2, 1 :3 or 1 :4 by weight ratio to each other.
  • the two surfactants may be used at about a 1 :1 by weight ratio to each other.
  • the compositions may include up to about 30% by weight surfactant, more particularly up to about 20% by weight surfactant, and more particularly still up to about 15% by weight surfactant. In select embodiments, the compositions may include between about 0.5% and about 15% by weight surfactant. In an embodiment, the compositions may include between about 2.0% and about 15% by weight, more particularly between about 3.0% and about 15% by weight surfactant. In select embodiments, the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, or about 15% by weight surfactant.
  • compositions herein comprise at least one carrier oil.
  • the carrier oil is an “oily medium”.
  • “oily medium” it is meant to refer to a medium capable of dissolving lipophilic or hydrophobic compounds, such as cannabinoids.
  • Particularly suitable carrier oils include natural oils as known in the art, for example, edible vegetable oils.
  • the carrier oils can include synthetic edible oils, for example, hydrogenated vegetable oils, medium chain triglyceride (MCT) oils, and the like and combinations thereof.
  • a non-limiting list of exemplary carrier oils includes a medium-chain triglyceride (MCT), a long-chain triglyceride (LOT), glycerine/glycerol, a monoglyceride (e.g.
  • glyceryl monostearate glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, PeceolTM), Labrasol, Labrafac Lipophile WL 1349, Labrafil M1944, Plural Oliqiue CC 497, Transcutol HP, Tween 20, Tween 40, Tween 45, Tween 60, Tween 65, Tween 80, Tween 81 , Tween 85, Gelucire 48/16, Vitamin E TPGS, and combinations thereof.
  • the at least one carrier oil is an MCT oil.
  • triglycerides in the MCT oil are esters derived from glycerol and three medium-chain fatty acids such as for example caproic acid, caprylic acid, capric acid, lauric acid, or any combination thereof.
  • the at least one carrier oil is an LCT oil.
  • triglycerides in the LCT oil are esters derived from glycerol and three long-chain fatty acids such as for example myristic acid, palmitic acid, stearic acid, arachidic acid, linoleic acid, or any combination thereof.
  • the at least one carrier oil is a coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, sesame oil.
  • the at least one carrier oil is comprised of monoglycerides.
  • the monoglycerides may be of a single type (e.g. glyceryl monolinoleate) or may be a mixture of different types.
  • the monoglycerides may include only the monoglyceride ester, or may include one or both of di- and triglycerides.
  • the monoglyceride fraction is predominant over the di- and triglyceride components.
  • the di- or triglyceride fractions may be predominant over the monoglycerides, such as for example in Maisine® CC.
  • the carrier oil is Maisine® CC.
  • the compositions may include up to about 25% by weight carrier oil, more particularly up to about 20% by weight carrier oil, and more particularly still up to about 15% by weight carrier oil. In select embodiments, the compositions may include between about 0.5% and about 25% by weight carrier oil. In an embodiment, the compositions may include between about 5% and about 20% by weight, and more particularly between about 10% and about 15% by weight carrier oil.
  • the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight carrier oil.
  • compositions or products may further include additives, such as for example and without limitation flavonoids, encapsulation materials, other additives (described below), or any combination thereof.
  • additives may be used to enhance flavour, viscosity, aroma and the like.
  • Terpenes, as described elsewhere herein, may also be included in the compositions or products of the present disclosure as an additive.
  • the additives may be derived from cannabis plants.
  • the additives may be derived from natural sources other than a cannabis plant, such as a plant of a different species.
  • the additives may be synthetic or semi-synthetic compounds.
  • compositions or products e.g. beverages, foodstuffs, etc.
  • the compositions or products may further include additives such as one or more flavonoids.
  • flavonoids refers to any compound of a large class of plant pigments having a structure based on or similar to that of flavone. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings and a heterocyclic ring.
  • flavonoids includes bioflavonoids, isoflavonoids and neoflavonoids.
  • Isoflavones use the 3-phenylchromen-4- one skeleton (with no hydroxyl group substitution on carbon at position 2). Examples include: Genistein, Daidzein, Glycitein, Isoflavanes, Isoflavandiols, Isoflavenes, Coumestans, and Pterocarpans.
  • flavonoids also includes anthocyanidins, anthoxanthins, flavanones, flavanonols and flavens. [00179] Flavonoids are widely distributed in plants, fulfilling many functions.
  • Flavonoids are the most important plant pigments for flower colouration, producing yellow or red/blue pigmentation in petals designed to attract pollinator animals. In higher plants, flavonoids are involved in UV filtration, symbiotic nitrogen fixation and floral pigmentation. They may also act as chemical messengers, physiological regulators, and cell cycle inhibitors. Some flavonoids have inhibitory activity against organisms that cause plant diseases, e.g. Fusarium oxysporum.
  • Sources of flavonoids include, without limitation, cannabis, parsley, blueberries, black tea, citrus, wine, cocoa and peanut.
  • Additional exemplary flavonoids for use in the compositions include Apigenin, beta-sitosterol, cannaflavin A, kaempferol, luteolin, orientin, quercetin and combinations thereof.
  • the flavonoid is cannaflavin.
  • compositions or products may include one or more encapsulation materials.
  • encapsulation materials A multitude of substances may be used to entrap, coat, or encapsulate materials.
  • the encapsulation material is one that has been certified for food applications as “generally recognized as safe” (GRAS).
  • the encapsulation material is of plant, marine, animal, or microbial origin.
  • the encapsulation material is a carbohydrate polymer, a protein, a lipid, or any combination thereof.
  • Exemplary and non-limiting carbohydrate polymers include starch, cellulose, plant exudates, plant extracts, polysaccharide, carrageenan, alginate, xanthan, gellan, dextran, chitosan, or any combination thereof.
  • Exemplary and non-limiting proteins includes hemp protein, gluten (e.g. corn), pea isolate, soy isolate, caseins, whey proteins, gelatin, or any combination thereof.
  • Exemplary and non-limiting lipids include fatty acids, fatty alcohols, glycerides, waxes, phospholipids, or any combination thereof.
  • the encapsulation materials form structure such as liposomes, micelles, or the like.
  • the encapsulation material is hemp protein.
  • compositions or products may include any number of other additives, including without limitation a solvent, a bulking agent, an antioxidant, or a nutritional supplement.
  • additives including without limitation a solvent, a bulking agent, an antioxidant, or a nutritional supplement.
  • these components may be used either alone or in combination to improve, for example, the chemical and/or physical properties, stability, nutritional profile, taste, colour and/or viscosity, of the compositions disclosed herein or a beverage or foodstuff produced therefrom.
  • the antioxidant may be ascorbyl palmitate or a-tocopherol.
  • modifiers and additives that may be used in the compositions or products (e.g. beverages, foodstuffs, etc.) disclosed herein include viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners (e.g. liquid sweeteners), and the like and combinations thereof, as known in the beverage and food arts, to provide improved solubility, stability, bioavailability, colour and taste.
  • Nutritional supplements comprise substances useful to the consumer of the compositions disclosed herein, or beverages or foodstuffs prepared therewith, for maintenance of normal body health.
  • Non-limiting examples of nutritional supplements may include essential nutrients including vitamins, dietary minerals, amino acids and fatty acids.
  • Exemplary nutritional supplements may include vitamin A, vitamin B1 , vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, vitamin C, vitamin D, vitamin E, vitamin K calcium, phosphorus, potassium, sulfur, sodium, chlorine, magnesium, iron, cobalt, copper, zinc, molybdenum, iodine, selenium, manganese, nickel, chromium, fluorine, boron, strontium histidine, isoleucine, leucine, lysine, methionine, cysteine, phenylalanine, tyrosine, threonine, tryptophan, valine, alpha-linoleic acid, and linoleic acid.
  • Viscosity modifiers include any compound or agent capable of altering the viscosity of the compositions disclosed herein, or a beverage or foodstuff produced therewith.
  • Exemplary embodiments of viscosity modifiers include anticaking agents, antifoaming agents, bulking agents, coagulation agents, gelling agents, glazing agents, humectants, leavening agents, tenderizers, and thickeners.
  • Sweeteners include any compound or agent that is capable of sweetening the taste of the compositions disclosed herein, or a beverage or foodstuff produced therewith.
  • the sweetener may be a natural sweetener or an artificial sweetener.
  • the sweetener may be a solid, liquid or semi-liquid.
  • Exemplary embodiments of sweeteners include sugars and sugar alcohols, and more particularly stevia, erythritol, and xylitol.
  • the sweetener may be a liquid sugar solution, such as without limitation those having a Brix value of about 67.5 °Bx.
  • the sweetener may be an Isocane 67.5 °Bx liquid sugar solution.
  • compositions of the present disclosure at least one cannabinoid and/or terpene, at least one surfactant, at least one saccharide, and at least one carrier oil are mixed, in any order.
  • methods for preparing the compositions disclosed herein comprise: combining at least one cannabinoid and/or terpene with at least one carrier oil to dissolve the cannabinoid in the carrier oil; separately preparing an aqueous solution comprising at least one saccharide; adding to the aqueous saccharide solution the cannabinoid and/or terpene/carrier oil solution and at least one surfactant; homogenizing and optionally subjecting the mixture to one or more passes through a microfluidizer; and spray drying the mixture to provide a solid powder.
  • heat may be applied.
  • the combining is performed under heated conditions of between about 40°C and about 75°C.
  • the cannabinoid and/or terpene and carrier oil may be combined with mixing or stirring, for example with a stir bar.
  • heating may also be applied to assist in dissolving the saccharide.
  • the heated conditions are between about 25°C and about 75°C.
  • the solution may be mixed to aid in complete solubilization of the saccharide, for example with a stir bar.
  • the components may be added in any order.
  • the at least one surfactant is added and mixed into the aqueous saccharide solution before adding the cannabinoid and/or terpene/carrier oil solution.
  • the solutions may be kept warm (e.g. between about 25°C and about 75°C) during this step.
  • mixing/stirring may be performed throughout this step to obtain a homogenous and uniform emulsion.
  • a minimal amount of ethanol may be used to dissolve and transfer any residual cannabinoid/carrier oil solution left behind in the beaker or container in which it was prepared.
  • the mixture can optionally be passed one or more times through a microfluidizer, for example to create an emulsion system with small particles.
  • any additives as described above are to be included in the composition, it may be suitable to mix the additives at any stage in any order.
  • the additives may be added into either the aqueous saccharide solution or the cannabinoid and/or terpene/carrier oil prior to combining these solutions.
  • a product may be prepared by mixing the powder composition with an aqueous solution or a foodstuff.
  • the product is a beverage.
  • the product is a sports drink beverage.
  • a product may also be prepared by first forming a liquid emulsion using the powder composition, and then adding the liquid emulsion to the beverage liquid or other foodstuff.
  • the product may comprise one or more of: terpenes, terpenoids, flavonoids, viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners, and combinations thereof.
  • PRODUCTS INCLUDING THE COMPOSITIONS
  • compositions disclosed herein are further directed to using the compositions disclosed herein to form end use products such as ingestibles and topical solids and liquids.
  • ingestibles can include, for example, beverages, liquids and foodstuffs.
  • compositions of the present disclosure may be used in the preparation of foodstuffs and beverages.
  • a beverage is any drink that may be consumed by a subject.
  • a foodstuff is any substance suitable for consumption as a food.
  • compositions may be combined with any beverage-compatible or food-compatible ingredient.
  • compositions of the present disclosure may be used directly in the preparation of foodstuffs and beverages, e.g. as an additive or ingredient.
  • Powder compositions may be used either directly, e.g. as an additive or ingredient, or indirectly e.g. by first dissolving the powder in a solvent (e.g. water) to form a liquid composition prior to use.
  • the powder compositions may be added to beverage or foodstuff directly.
  • the powder compositions are diluted with a bulking agent.
  • the pre-bulked and/or bulked powder compositions can be packaged for individual servings (e.g. sachets/packets), packages in bulk within a single container, or a combination thereof.
  • beverage liquids are liquids meeting the common meaning of the term "biocompatible", which include materials that are not harmful to living tissue.
  • beverage liquids comprise water, oil, alcohol; with or without additives or modifiers or both.
  • beverage liquids can be divided into various groups such as plain/stil I water, carbonated water, alcohol, non-alcoholic drink, soft drinks, electrolyte drinks (e.g. sports drink beverages), fruit juice, vegetable juice, tea, coffee, milk, or other hot, room temperature or cold liquids used in drinks.
  • Beverages can be caffeinated or non-caffeinated and may contain calories or not.
  • Such beverages may be produced in ready to use form or be produced in a form suitable for preparation in final consumable form at or proximate to the time of ingestion.
  • beverage liquids will make up between about 50% and 99.99% by weight or by volume of the beverage.
  • beverage liquids will make up between about 60% and about 99.99% by weight or by volume of the beverage, more particularly between about 70% and about 99.99% by weight or by volume of the beverage, more particularly still between about 80% to about 99.99% by weight or by volume of the beverage, and even more particularly still between about 80% to about 99.99% by weight or by volume of the beverage.
  • the beverage liquid will make up between about 80% and about 99.99% by weight of the beverage.
  • the beverage liquid will make up between about 80% and about 99.9% by weight of the beverage, between about 80% and about 99%, or between about 80% and about 90% by weight of the beverage.
  • the beverage liquid will make up between about 95% and about 99.9% by weight of the beverage. In an embodiment, the beverage liquid will make up about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99%, or more by weight of the beverage. In an embodiment, the beverage liquid will make up about 99.0%, about 99.1%, about 99.2%, about 99.3%, about 99.4%, about 99.5%, about 99.6%, about 99.7%, about 99.8%, or about 99.9% by weight of the beverage. In an embodiment, the beverage liquid is water. In an embodiment, additives may be present in addition to the quantity of beverage liquid. In an embodiment, a liquid additive (e.g. sweetener) may be present in addition to the quantity of beverage liquid.
  • a liquid additive e.g. sweeten
  • the beverage liquid will make up between about 80% and about 95% by weight of the beverage, and a liquid additive (e.g. sweetener) will make up between about 4.9% and about 14.9% by weight of the beverage.
  • a liquid additive e.g. sweetener
  • the beverage liquid will make up about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95% by weight of the beverage.
  • a liquid additive e.g.
  • the beverage liquid is water and the liquid additive is a liquid sweetener, such as for example a 67.5 °Bx (Brix) sugar solution.
  • Non-limiting examples of beverages that may be prepared with the compositions of the present disclosure include but are not limited to: hot and cold beverages including water, fruit juice, vegetable juice, tea, coffee, softs drinks, sports drinks, energy drinks, alcohol, flavoured water, or single-serve beverage cartridges.
  • Non-limiting examples of foodstuffs include baked goods (e.g. cookies, brownies, cake, pie, biscuits and pastries), candies (e.g. hard candy, soft candy, gummies, etc.), chocolates, lozenges, gum, mints, dried fruits, nuts, granola, truffles, caramels, chews, taffy, prepared meals, cooking ingredients (e.g. food additives, dry spices, honey, sugar, sweeteners, etc.), ground coffee, instant coffee and tea leaves.
  • baked goods e.g. cookies, brownies, cake, pie, biscuits and pastries
  • candies e.g. hard candy, soft candy, gummies, etc.
  • chocolates lozenges, gum, mints, dried fruits
  • the amount of the compositions of the present disclosure added to beverages or foodstuffs will vary depending on the desired dosage of cannabinoids.
  • each serving, unit or item of foodstuff or beverage will contain between about 0.5 mg and about 100 mg of cannabinoids.
  • the foodstuff or beverage will contain between about 1.0 mg and about 50 mg of cannabinoids, more particularly between about 1.0 mg and about 25 mg of cannabinoids, between about 2.0 mg and about 20 mg, or between about 2.0 mg and about 10 mg of cannabinoids.
  • the foodstuff or beverage will contain about 0.5 mg, about 1.0 mg, about 1.5 mg, about 2.0 mg, about 2.5 mg, about 3.0 mg, about 3.5 mg, about 4.0 mg, about 4.5 mg, about 5.0 mg, about 5.5 mg, about 6.0 mg, about 6.5 mg, about 7.0 mg, about 7.5 mg, about 8.0 mg, about 8.5 mg, about 9.0 mg, about 9.5 mg, about 10.0 mg, about 10.5 mg, about 11.0 mg, about 11.5 mg, about 12.0 mg, about 12.5 mg, about 13.0 mg, about 13.5 mg, about 14.0 mg, about 14.5 mg, about 15.0 mg, about
  • the foodstuff or beverage may contain a cannabinoid concentration of between about 0.01 mg/mL and about 2.5 mg/mL, more particularly between about 0.025 mg/mL and about 1.25 mg/mL, between about 0.025 mg/mL and about 1.0 mg/mL, or between about 0.05 mg/mL and about 0.1 mg/mL.
  • the foodstuff or beverage may contain a cannabinoid concentration of about 0.01 mg/mL, about 0.02 mg/mL, about 0.03 mg/mL, about 0.04 mg/mL, about 0.05 mg/mL, about 0.06 mg/mL, about 0.07 mg/mL, about 0.08 mg/mL, about 0.09 mg/mL, about 0.1 mg/mL, about 0.2 mg/mL, about 0.3 mg/mL, about 0.4 mg/mL, about 0.5 mg/mL, about 0.6 mg/mL, about 0.7 mg/mL, about 0.8 mg/mL, about 0.9 mg/mL, about 1.0 mg/mL, about 1.25 mg/mL, about
  • the cannabinoid may be one type of cannabinoid (e.g. CBD or THC) or any combination of cannabinoids.
  • the cannabinoid is THC.
  • the cannabinoid is CBD.
  • the product e.g. beverage or foodstuff
  • the product may comprise between about 0.1% and about 25% by weight, particularly about 0.5% and about 25% by weight of the composition as disclosed herein, more particularly between about 1% and about 10% by weight of the composition, and more particularly still between about 1% and about 5% by weight of the composition.
  • the product may comprise between about 0.5% and about 3% by weight of the composition.
  • low quantities by weight of the composition may be used due to advantageous properties of the compositions of the present disclosure in stably formulating cannabinoids and/or terpenes.
  • the compositions may be mixed with an aqueous solution to prepare an end use product (e.g. beverage).
  • the aqueous solution can include pure water alone, or an aqueous solution including water and additives such as the additives described above to improve end use product stability, bioavailability, colour, aroma and taste.
  • additives may include terpenes, terpenoids, flavonoids, viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners (liquid and/or solid), and the like and combinations thereof, as known in the beverage and food arts.
  • Beverages may be packaged as individual packages, suitably single use packages, and multiple packages.
  • the packaging can be in air tight containers.
  • Packaging may be comprised of paper, plastic, metal, and glass.
  • the packaging may be Tetra PakTM packaging.
  • Beverages may include bubble containing or producing liquids with dissolved gas or liquids capable of producing gas proximately in time of consumption.
  • the beverages optionally comprising additives, modifiers or both, are convenient to consumers, and are manufactured at modest expense.
  • Beverages with dissolved gas may be created by a method comprising addition of carbon dioxide, ozone, oxygen, and nitrogen.
  • dissolved gas may be added to the beverage by methods comprising application of pressure, and adding water with the dissolved gas. The dissolved gas is released from the beverage when pressure is reduced as effervescence.
  • compositions are absorbed into a solid material for use as an end use product.
  • the compositions may be absorbed onto one or more of blotter paper, tea leaves, coffee grounds, spices, beverage cap and the like to allow for a convenient beverage, edible or tea bag.
  • select embodiments of the products comprising or produced using the water-soluble compositions of the present disclosure are shelf-stable.
  • shelf-stable refers to the composition maintaining its water-soluble nature in an aqueous product at least in respect of the cannabinoid (e.g., no precipitation) for a period of at least 30 days, more suitably, at least 40 days, even more suitably, at least 45 days, and more suitably, at least 50 days, and even more suitably, at least 55 days or longer.
  • the product may have a reduced oxygen content, such as by removing the oxygen by means of equipment designed to perform this function or by chemical removal (e.g. N2 purge and/or potassium disulfite).
  • the oxygen content of the product is between about 0 ppm and about 500 ppm.
  • the product is sealed until use in order to maintain the reduced oxygen content.
  • Exemplary powder compositions according to the present disclosure, and as described in Table 1 were prepared generally as follows. [00223] A cannabinoid was dissolved in carrier oil with the application of heat. Separately, an aqueous saccharide solution was prepared and to the solution was added the carrier oil (comprising the cannabinoid) and a surfactant, forming a mixture. The beaker that had contained the cannabinoid and carrier oil was rinsed with small volumes of ethanol, and the ethanol washings were also added to the mixture.
  • the mixture was homogenized and subjected to one or more passes through a microfluidizer (with the exception of the mixtures used to prepare Compositions 3, 4, 6 and 9 which were not passed through a microfluidizer).
  • the mixture was then spray dried with nitrogen and the resulting solid powder was isolated for analysis and characterization.
  • compositions were tested for solubility/dispersibility in either water or a sports drink beverage.
  • compositions 1-7 were tested in water and all displayed solubility and dispersability within 5 minutes with stirring, with the exception of compositions 1 , 2 and 3 which were only partially dispersed after 5 minutes and required slightly more time to become totally dispersed. After being left standing for 30 minutes there was no change and the compositions remained solubilized/dispersed in the water (no precipitate).
  • compositions 8-10 were tested in two different sports drink beverages and all displayed solubility and dispersability within 2 minutes with stirring. Composition 10 displayed foaming after initial stirring, which resolved shortly thereafter. After being left standing for 60 minutes there was no change and the compositions remained solubilized/dispersed in the water (no precipitate).
  • Example 1 An exemplary powder composition according to the present disclosure was prepared according to Example 1.
  • the composition comprised the following components:
  • Example 1 An exemplary powder composition according to the present disclosure was prepared according to Example 1.
  • the composition comprised the following components:
  • Example 1 An exemplary powder composition according to the present disclosure was prepared according to Example 1.
  • the composition comprised the following components:
  • Particle size distribution (in water) for the above composition was found to be an average particle size of 107 nm, with a polydispersity of 0.1.
  • all terms referred to in singular form are meant to encompass plural forms of the same. Likewise, all terms referred to in plural form are meant to encompass singular forms of the same. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains.
  • compositions and methods are described in terms of “comprising,” “containing,” or “including” various components or steps, the compositions and methods can also “consist essentially of or “consist of the various components and steps.
  • indefinite articles “a” or “an,” as used in the claims, are defined herein to mean one or more than one of the element that it introduces.
  • ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • any numerical range with a lower limit and an upper limit is disclosed, any number and any included range falling within the range are specifically disclosed.
  • every range of values (of the form, "from about a to about b,” or, equivalently, “from approximately a to b,” or, equivalently, “from approximately a-b") disclosed herein is to be understood to set forth every number and range encompassed within the broader range of values even if not explicitly recited.
  • every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.

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Abstract

Water-soluble compositions including cannabinoids for use in beverages and foods, methods of preparing the compositions, and methods of preparing beverages and foods including the compositions are disclosed herein. The compositions comprise at least one cannabinoid, at least one saccharide, at least one surfactant, and at least one carrier oil.

Description

WATER-SOLUBLE CANNABINOID COMPOSITIONS, METHODS OF MAKING AND USE
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application claims priority to and benefit of United States Patent Application Serial No. 63/240,365 filed on September 2, 2021 , which is hereby incorporated by reference in its entirety.
TECHNICAL FIELD
[0002] The present disclosure generally relates to water-soluble cannabinoid and/or terpene compositions, and more particularly to compositions comprising cannabinoids and/or terpenes that may be used in the preparation of beverages, topicals, foodstuffs, and other products.
BACKGROUND
[0003] In the cannabis industry, an important aspect of preparing a commercial product is the ability to formulate cannabinoids and terpenes in a desirable form for human consumption.
[0004] Smoking is not typically acceptable to non-smokers, as it can be aesthetically unpleasant and can involve health risks such as irritation to at least the mouth, esophagus and lungs. Cigarette smoking has been linked to devastating health risks thought to result from the formation of harmful combustion products. In some jurisdictions, legislation exists which prohibits smoking in various locations and cannabis smoking itself is the target of regulation due to so-called “second hand smoke” risks, as well as what is said to be unpleasant smells for some people. Methods for consuming cannabis, and more particularly cannabinoids, which do not involve smoking or other vaporous means of ingestion may therefore be advantageous as such methods do not involve these and other unwanted effects.
[0005] Oral consumption comprises a significant percentage of total cannabis use in federally legal jurisdictions as well as on a state, province, or the like, basis globally. Many orally consumable products, however, may contain unhealthy amounts of substances other than cannabinoids. Further, many known oral products use expensive additives, which are cost prohibitive and may also have unpredictable supply.
[0006] As hydrophobic compounds, cannabinoids present challenges for preparing desirable consumer products, such as beverages and other foodstuffs. Cannabinoids, including many cannabinoid extracts and oils, are insoluble in water thereby making many food products and beverages difficult to produce, including difficulties in obtaining desirable concentrations, dispersibility, and stability of cannabinoids in these products. Emulsions of cannabinoids have been used, but challenges arise in obtaining compositions capable of providing desirable particle size distribution characteristics. These factors are particularly relevant in preparing consumer products having high ionic strengths (e.g. sports drinks).
[0007] A need therefore exists for improved water-soluble compositions of cannabinoids and/or terpenes that may be used in the preparation of consumer products, and in particular aqueous-based products such as beverages, including sports drink beverages. There further exists a need that these compositions have wide-range applicability in preparing consumer products.
SUMMARY
[0008] The present disclosure provides a convenient water-soluble composition of cannabinoids and/or terpenes that may be used in beverages, foodstuffs and other recreational and/or medicinal products. More particularly, in select embodiments, the present disclosure provides a composition of cannabinoids and/or terpenes for use in liquid or powder forms that is soluble in water, and capable of improving the dispersibility and stability of cannabinoids to provide for acceptable shelf-life and consumer appeal (e.g. lack of sediment, homogeneous appearance, etc.) of the products produced therefrom, such as for example beverages. Most suitably, and in select embodiments, the water-soluble compositions are physically and chemically stable.
[0009] The present disclosure is directed to such cannabinoid and/or terpene compositions for use in beverages, foods and other products, and to methods of preparing the compositions. The present disclosure is also directed to foodstuffs and beverages comprising said compositions (e.g. produced using the compositions of the present disclosure). [0010] In an embodiment, the present disclosure relates to a composition comprising: at least one cannabinoid and/or terpene; at least one saccharide; at least one surfactant; and at least one carrier oil.
[0011] The present disclosure is also directed to methods of preparing the compositions that are commercially-viable, efficient, and capable of producing shelf-stable products, such as beverages and foodstuffs.
[0012] The present disclosure is also directed to a beverage or foodstuff comprising the composition of the present disclosure.
[0013] Without being bound by any particular theory, the compositions of the present disclosure may improve the ability to formulate cannabinoids and/or terpenes into aqueous mediums (e.g. beverages and foodstuffs), and in particular sports drink beverages.
[0014] Other aspects and features of the water-soluble compositions, methods and products (e.g. beverages, foodstuffs, and dosage forms) of the present disclosure will become apparent to those ordinarily skilled in the art upon review of the following description of specific embodiments.
BRIEF DESCRIPTON OF THE DRAWINGS
[0015] The appended drawings illustrate one or more embodiments of the present disclosure by way of example only and are not to be construed as limiting the scope of the present disclosure.
[0016] FIG. 1 depicts a particle size distribution graph of an exemplary composition (Composition 1).
[0017] FIG. 2 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 2).
[0018] FIG. 3 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 3). [0019] FIG. 4 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 4).
[0020] FIG. 5 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 5).
[0021] FIG. 6 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 6).
[0022] FIG. 7 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 7).
[0023] FIG. 8 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 8).
[0024] FIG. 9 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 9).
[0025] FIG. 10 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 10).
[0026] FIG. 11 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 11).
[0027] FIG. 12 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 12).
[0028] FIG. 13 depicts a particle size distribution graph of an exemplary composition of the present disclosure (Composition 13).
[0029] FIG. 14 depicts a particle size distribution graph of an exemplary composition (Composition 14).
DETAILED DESCRIPTION
[0030] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the disclosure belongs. Although any methods and materials similar to or equivalent to those described herein can be used in the practice or testing of the present disclosure, the suitable methods and materials are described below.
[0031] The present disclosure is generally directed to water-soluble cannabinoid and/or terpene compositions, methods for their preparation, and use thereof. The compositions are suitably in a nontoxic consumable liquid form or a dispersible powder form. The compositions may also be absorbed, sprayed or otherwise applied into or onto a solid material (e.g. a tea bag). Suitably, embodiments of the compositions disclosed herein provide stability, solubility in water, have minimal flavour and odor, and are natural in origin.
[0032] The compositions of the present disclosure include a cannabinoid and/or a terpene, and in particular, may include a cannabinoid distillate and/or a cannabinoid isolate. Cannabis has been used in beverage preparations for years. Most of the historical cannabis beverages were prepared by boiling or grinding cannabis leaves, combining with water, milk, alcohol, or another biocompatible matrix or beverage liquid and, optionally, mixing with herbal or other plant-based compositions to form the final consumable.
[0033] In an embodiment, the present disclosure provides improved compositions for cannabinoids. As shown herein, the compositions of the present disclosure comprising at least one cannabinoid, at least one saccharide, at least one surfactant, and at least one carrier oil are highly soluble/dispersible in aqueous mediums (e.g. Example 1 ).
[0034] Sports drink beverages may present unique formulation challenges for cannabinoids due to the presence of salts (e.g. electrolytes), flavours or other components that may impact solubility, dispersibility, and/or stability. The water soluble compositions of the present disclosure were yet capable of preparing cannabinoid-infused sports drink beverages with desirable physical and chemical stability properties (e.g. Example 1 ).
[0035] Thus, in an embodiment, the present disclosure provides convenient water- soluble compositions of cannabinoids that may be readily used in the preparation of beverages and foodstuffs.
[0036] COMPOSITIONS
[0037] The compositions of the present disclosure comprise at least one cannabinoid and/or terpene, at least one saccharide, at least one surfactant, and at least one carrier oil. For ease of reference, ratios and amounts are often described throughout the present disclosure by reference to “cannabinoid” (e.g. a ratio of cannabinoid:surfactant). It should be understand that such ratios and amounts are equally applicable to terpene(s) in embodiments where one or more terpenes are included (e.g. a ratio of terpene:surfactant).
[0038] As used herein, the term “composition” is meant to refer broadly to any product or material comprised of two or more components (e.g. a cannabinoid and/or terpene, a saccharide, a surfactant and a carrier oil). A “formulation” is meant to define the composition according to a particular physical state (e.g. powder or liquid) or the act, process or result of formulating according to a particular formula. In the context of the present disclosure, any features described for compositions of the present disclosure may also apply to formulations, and vice versa.
[0039] The compositions herein serve as a convenient water-soluble dosage form of cannabinoids and/or terpenes for use in beverages, topicals and foodstuffs. The compositions are suitably in a nontoxic consumable liquid or solid form.
[0040] As used herein, “water-soluble” has its ordinary meaning in referring to the ability of a composition or component thereof to dissolve when the object is placed in water. For example, when the object is mixed with water at room temperature or slightly above (e.g. about 25°C to about 50°C).
[0041] In select embodiments, the components of the compositions disclosed herein are at particular ratios to one another. Without being bound by any particular theory, the particular ratio of components present in the compositions of the present disclosure may improve the ability to formulate cannabinoids into aqueous mediums (e.g. beverages and foodstuffs) to provide a desirable product.
[0042] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of cannabinoid:surfactant of between 50:1 and 1 :50, between 25:1 and 1 :25, between 10:1 and 1 :10, between 9:1 and 1 :9, between 8:1 and 1 :8, between 7:1 and 1:7, between 6:1 and 1 :6, between 5:1 and 1 :5, between 4:1 and 1 :4, between 3:1 and 1 :3, or between 2:1 and 1 :2 by weight. In an embodiment, the ratio of cannabinoid:surfactant may be between 10:1 and 1 :5, between 5:1 and 1 :2.5, or between 2.5:1 and 1 :2.5 by weight. In an embodiment, the ratio of cannabinoid:surfactant may be about 10:1 , about 9:1 , about 8:1, about 7:1 , about 6:1 , about 5:1 , about 4:1 , about 3:1 , about 2:1 , about 1 :1 , about 1 :1.5, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight.
[0043] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of cannabinoid:carrier oil of between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight. In an embodiment, the ratio of cannabinoid:carrier oil may be between 1:1 and 1:2 by weight. In an embodiment, the ratio of cannabinoid:carrier oil may be about 10:1, about 9:1, about 8:1, about 7:1 , about 6:1, about 5:1 , about 4:1, about 3:1 , about 2:1, about 1:1, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight.
[0044] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of cannabinoid:saccharide of between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1 :2 by weight. In an embodiment, the ratio of cannabinoid:saccharide may be between 1:1 and 1:25, between 1:2 and 1:15, or between 1:5 and 1:10 by weight. In an embodiment, the ratio of cannabinoid:saccharide may be about 10:1, about 9:1, about 8:1, about 7:1, about 6:1 , about 5:1, about 4:1 , about 3:1, about 2:1 , about 1:1, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, about 1:10, about 1:11, about 1:12, about 1:13, about 1:14, about 1:15, about 1:16, about 1:17, about 1:18, about 1:19, about 1 :20, about 1 :21 , about 1 :22, about 1 :23, about 1 :24, or about 1 :25 by weight.
[0045] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide:surfactant of between 100:1 and 1:100, between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1 :3, or between 2:1 and 1 :2 by weight. In an embodiment, the ratio of saccharide:surfactant may be between 50:1 and 1:1, between 45:1 and 1:1, between 40:1 and 1:1, between 35:1 and 1:1, between 35:1 and 2:1, or between 35:1 and 3:1 by weight. In an embodiment, the ratio of saccharide:surfactant may be between 40:1 and 1:2 by weight. In an embodiment, the ratio of saccharide:surfactant may be about 100:1, about 75:1, about 50:1 , about 45:1, about 40: 1 , about 35: 1 , about 30: 1 , about 25: 1 , about 20: 1 , about 15:1, about 14:1, about 13:1, about 12:1, about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1, about 5:1 , about 4.5:1, about 4:1 , about 3.5:1, about 3:1, about 2.5:1, about 2:1, about 1.5:1, about 1:1, about 1:2, about 1:3, about 1:4, or about 1:5 by weight.
[0046] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide:carrier oil of between 50:1 and 1:50, between 25:1 and 1:25, between 15:1 and 1:1, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight. In an embodiment, the ratio of saccharide:carrier oil may be between 15:1 and 1:1, between 14:1 and 1:1, between 13:1 and 1:1, between 12:1 and 1:1, between 11:1 and 1:1, between 10:1 and 1:1, between 9:1 and 1:1, between 8:1 and 7:1, between 6:1 and 1:1, between 5:1 and 1:1, between 4:1 and 1:1, between 3:1 and 1:1, or between 2:1 and 1:1 by weight. In an embodiment, the ratio of saccharide:carrier oil may be about 25:1, about 20:1, about 15:1 , about 14:1, about 13:1, about 12:1, about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1, about 5:1, about 4.5:1 , about 4:1, about 3.5:1, about 3:1, about 2.5:1, about 2:1, about 1.5:1, about 1:1, about 1:2, about 1:3, about 1 :4, or about 1 :5 by weight.
[0047] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of carrier oiksurfactant of between 50:1 and 1:50, between 25:1 and 1:25, between 10:1 and 1:10, between 9:1 and 1:9, between 8:1 and 1:8, between 7:1 and 1:7, between 6:1 and 1:6, between 5:1 and 1:5, between 4:1 and 1:4, between 3:1 and 1:3, or between 2:1 and 1:2 by weight. In an embodiment, the ratio of carrier oiksurfactant may be between 10:1 and 1:5, between 5:1 and 1:2.5, or between 2.5:1 and 1:2.5 by weight. In an embodiment, the ratio of carrier oiksurfactant may be between 15:1 and 1:5, and more particularly between 12:1 and 1 :2 by weight. In an embodiment, the ratio of carrier oiksurfactant may be about 15:1 , about 14:1, about 13:1, about 12:1 , about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1 , about 5:1, about 4:1 , about 3:1, about 2:1 , about 1:1, about 1:1.5, about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, or about 1:10 by weight. [0048] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight.
[0049] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight.
[0050] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight.
[0051] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5-2 : 1 by weight.
[0052] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight.
[0053] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight.
[0054] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight.
[0055] In an embodiment, the compositions of the present disclosure and/or products produced therefrom (e.g. beverages or foodstuffs) may include a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight.
[0056] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta glucan, glycogen, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a polyglyceryl ester, a Vitamin E TPGS, saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, glycerine/glycerol, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CO, Peceol™), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of cannabinoid:saccharide of between 50:1 and 1 :50, and/or a ratio of saccharide:surfactant of between 100:1 and 1 :100, and/or a ratio of saccharide:carrier oil of between 50:1 and 1 :50 by weight. The ratio of cannabinoid:saccharide, saccharide:surfactant and saccharide:carrier oil may be any ratio within the disclosed ranges, and in some embodiments may be the ratios as disclosed elsewhere herein.
[0057] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta glucan, glycogen, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a polyglyceryl ester, a Vitamin E TPGS, saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, glycerine/glycerol, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CO, Peceol™), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5- 2 : 1 by weight. The ratio of saccharide : carrier oil : surfactant may be any ratio within the disclosed ranges.
[0058] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta glucan, glycogen, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a polyglyceryl ester, a Vitamin E TPGS, saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, glycerine/glycerol, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, Peceol™), a Vitamin E TPGS, coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, or sesame oil, wherein the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight. The ratio of saccharide : cannabinoid : carrier oil : surfactant may be any ratio within the disclosed ranges.
[0059] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a Vitamin E TPGS, or saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, Peceol™), or a Vitamin E TPGS, wherein the composition has a ratio of cannabinoid:saccharide of between 50:1 and 1 :50, and/or a ratio of saccharide:surfactant of between 100:1 and 1 :100, and/or a ratio of saccharide:carrier oil of between 50:1 and 1 :50. The ratio of cannabinoid:saccharide, saccharide:surfactant and saccharide:carrier oil may be any ratio within the disclosed ranges, and in some embodiments may be the ratios disclosed elsewhere herein.
[0060] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a Vitamin E TPGS, saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, Peceol™), or a Vitamin E TPGS, wherein the composition has a ratio of saccharide : carrier oil : surfactant of 0.5-40 : 0.2-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 3-40 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 15-40 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : carrier oil : surfactant of 3-7 : 0.5- 2 : 1 by weight. The ratio of saccharide : carrier oil : surfactant may be any ratio within the disclosed ranges.
[0061] In an embodiment, the composition of the present disclosure comprises: at least one cannabinoid from THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, or cannabicitran; at least one saccharide from inositol, myo-inositol, inulin, pectin, or maltodextrin; at least one surfactant from an ethoxylated sorbitan ester, a Vitamin E TPGS, saponins, or gum arabic; and at least one carrier oil from medium-chain triglycerides, long-chain triglycerides, monoglycerides (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CO, Peceol™), or a Vitamin E TPGS, wherein the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 0.5-40 : 0.2-8 : 0.2-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-40 : 0.25-8 : 0.5-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 15-40 : 3-8 : 3-12 : 1 by weight. In some embodiments, the composition has a ratio of saccharide : cannabinoid : carrier oil : surfactant of 3-7 : 0.25-2 : 0.5-2 : 1 by weight. The ratio of saccharide : cannabinoid : carrier oil : surfactant may be any ratio within the disclosed ranges.
[0062] In select embodiments, the water-soluble compositions, dosage forms, beverages or foodstuffs of the present disclosure may provide fast onset of biological effects of the cannabinoids in human or animal consumers or subjects. The compositions of the present disclosure may provide advantageous properties for formulating products (e.g. beverages and foodstuffs) which are capable of by-passing first pass metabolism and thereby improving bioavailability of cannabinoids.
[0063] Cannabinoids
[0064] In an embodiment, the compositions of the present disclosure comprise at least one cannabinoid. In such embodiments, the compositions may comprise a single cannabinoid (e.g. THC, CBD or another cannabinoid) or may comprise any combination of two or more cannabinoids (e.g. CBD and THC). The compositions may also comprise at least one terpene in combination with the at least one cannabinoid.
[0065] As used herein, the term “cannabinoid” refers to a compound belonging to a class of secondary compounds commonly found in plants of genus cannabis, but also encompasses synthetic and semi-synthetic cannabinoids. [0066] In an embodiment, a cannabinoid is one of a class of diverse chemical compounds that acts on cannabinoid receptors such as CB1 and CB2 in cells that alter neurotransmitter release in the brain. One of the most notable cannabinoids of the phytocannabinoids is tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is another cannabinoid that is a major constituent of the plant. There are at least 113 different cannabinoids isolated from cannabis, exhibiting varied effects.
[0067] In an embodiment, the cannabinoid is a compound found in a plant, e.g., a plant of genus cannabis, and is sometimes referred to as a phytocannabinoid. In an embodiment, the cannabinoid is a compound found in a mammal, sometimes called an endocannabinoid. In an embodiment, the cannabinoid is made in a laboratory setting, sometimes called a synthetic cannabinoid. In one embodiment, the cannabinoid is derived or obtained from a natural source (e.g. plant) but is subsequently modified or derivatized in one or more different ways in a laboratory setting, sometimes called a semi-synthetic cannabinoid.
[0068] Synthetic cannabinoids and semisynthetic cannabinoids encompass a variety of distinct chemical classes, for example and without limitation: the classical cannabinoids structurally related to THC, the non-classical cannabinoids (cannabimimetics) including the aminoalkylindoles, 1 ,5-diarylpyrazoles, quinolines, and arylsulfonamides as well as eicosanoids related to endocannabinoids.
[0069] In many cases, a cannabinoid can be identified because its chemical name will include the text string “*cannabi*”. However, there are a number of cannabinoids that do not use this nomenclature, such as for example those described herein.
[0070] Within the context of this disclosure, where reference is made to a particular cannabinoid, each of the acid and/or decarboxylated forms are contemplated as both single molecules and mixtures. In addition, salts of cannabinoids are also encompassed, such as salts of cannabinoid carboxylic acids.
[0071] As well, any and all isomeric, enantiomeric, or optically active derivatives are also encompassed. In particular, where appropriate, reference to a particular cannabinoid incudes both the “A Form” and the “B Form”. For example, it is known that THCA has two isomers, THCA-A in which the carboxylic acid group is in the 1 position between the hydroxyl group and the carbon chain (A Form) and THCA-B in which the carboxylic acid group is in the 3 position following the carbon chain (B Form).
[0072] Examples of cannabinoids include, but are not limited to, Cannabigerolic Acid (CBGA), Cannabigerolic Acid monomethylether (CBGAM), Cannabigerol (CBG), Cannabigerol monomethylether (CBGM), Cannabigerovarinic Acid (CBGVA), Cannabigerovarin (CBGV), Cannabichromenic Acid (CBCA), Cannabichromene (CBC), Cannabichromevarinic Acid (CBCVA), Cannabichromevarin (CBCV), Cannabidiolic Acid (CBDA), Cannabidiol (CBD), A6-Cannabidiol (A6-CBD), Cannabidiol monomethylether (CBDM), Cannabidiol-C4 (CBD-C4), Cannabidivarinic Acid (CBDVA), Cannabidivarin (CBDV), Cannabidiorcol (CBD-C1), Tetrahydrocannabinolic acid A (THCA-A), Tetrahydrocannabinolic acid B (THCA-B), Tetrahydrocannabinol (THC or A9-THC), A8-tetrahydrocannabinol (A8-THC), trans-A10-tetrahydrocannabinol (trans-A10-THC), c/s-A10-tetrahydrocannabinol (c/s-A10-THC), Tetrahydrocannabinolic acid C4 (THCA-C4), Tetrahydrocannbinol C4 (THC C4), Tetrahydrocannabivarinic acid (THCVA), Tetrahydrocannabivarin (THCV), A8-Tetrahydrocannabivarin (A8-THCV), A9-Tetrahydrocannabivarin (A9-THCV), Tetrahydrocannabiorcolic acid (THCA-C1), Tetrahydrocannabiorcol (THC-C1 ), A7-c/s-iso-tetrahydrocannabivarin, A8-tetrahydrocannabinolic acid (A8-THCA), A9-tetrahydrocannabinolic acid (A9-THCA), Cannabicyclolic acid (CBLA), Cannabicyclol (CBL), Cannabicyclovarin (CBLV), Cannabielsoic acid A (CBEA-A), Cannabielsoic acid B (CBEA-B), Cannabielsoin (CBE), Cannabinolic acid (CBNA), Cannabinol (CBN), Cannabinol methylether (CBNM), Cannabinol-C4 (CBN-C4), Cannabivarin (CBV), Cannabino-C2 (CBN-C2), Cannabiorcol (CBN-C1), Cannabinodiol (CBND), Cannabinodivarin (CBDV), Cannabitriol (CBT), 11-hydroxy-A9-tetrahydrocannabinol (11-OH-THC), 11-nor-9-carboxy-A9- tetrahydrocannabinol, Ethoxy-cannabitriolvarin (CBTVE), 10-Ethoxy-9-hydroxy-A6a- tetrahydrocannabinol, Cannabitriolvarin (CBTV), 8,9-Dihydroxy-A6a(10a)- tetrahydrocannabinol (8,9-Di-OH-CBT-C5), Dehydrocannabifuran (DCBF), Cannbifuran (CBF), Cannabichromanon (CBCN), Cannabicitran, 10-Gxo-A6a(10a)-tetrahydrocannabinol (OTHC), A9-cis-tetrahydrocannabinol (cis-THC), Cannabiripsol (CBR), 3,4,5,6-tetrahydro-7- hydroxy-alpha-alpha-2-trimethyl-9-n-propyl-2,6-methano-2H-1-benzoxocin-5-methanol (OH- iso-HHCV), Trihydroxy-delta-9-tetrahydrocannabinol (triOH-THC), Yangonin, Epigallocatechin gallate, Dodeca-2E, 4E, 8Z, 10Z-tetraenoic acid isobutylamide, hexahydrocannibinol, and Dodeca-2E,4E-dienoic acid isobutylamide. [0073] In an embodiment, the cannabinoid is a cannabinoid dimer. The cannabinoid may be a dimer of the same cannabinoid (e.g. THC — THC) or different cannabinoids. In an embodiment, the cannabinoid may be a dimer of THC, including for example cannabisol.
[0074] As used herein, the term “THC” refers to tetrahydrocannabinol. “THC” refers to and is used interchangeably herein with “A9-THC”.
[0075] In an embodiment, the at least one cannabinoid is THC (A9-THC), A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, CBT, cannabicitran, or any acid form thereof, or any combination of any of the foregoing.
[0076] Structural formulae of cannabinoids of the present disclosure may include the following:
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
cannabicitran
(cannabitriol)
[0077] In an embodiment, the at least one cannabinoid is THC, CBD, CBN, CBG, CBGA, or any combination thereof.
[0078] In an embodiment, the at least one cannabinoid is THC (A9-THC), A8-THC, trans-M 0-THC, c/s-A10-THC, THCV, A8-THCV, A9-THCV, CBD, CBDV, CBC, CBG, CBL, CBN, CBT, or any acid form thereof, or any combination of any of the foregoing.
[0079] In an embodiment, the at least one cannabinoid is THC, CBD, or a combination thereof.
[0080] In an embodiment, the at least one cannabinoid is THC.
[0081] In an embodiment, the at least one cannabinoid is CBD.
[0082] In an embodiment, the at least one cannabinoid comprises more than one cannabinoid, and in particular, a combination of THC and CBD.
[0083] In select embodiments of the compositions disclosed herein, the at least one cannabinoid may be introduced in the form of a pure or purified cannabinoid. As used herein, the term “purified” or “pure” means extracted, isolated, and/or separated from other compounds, formulations, compositions, matter, and/or mass resulting in a greater than 60% purity. A non-limiting example of a purified cannabinoid is a cannabinoid isolate.
[0084] In some embodiments a “purified” cannabinoid is greater than about 70% pure, greater than about 75% pure, greater than about 80% pure, greater than about 85% pure, greater than about 90% pure, greater than about 91% pure, greater than about 92% pure, greater than about 93% pure, greater than about 94% pure, greater than about 95% pure, greater than about 96% pure, greater than about 97% pure, greater than about 98% pure, or greater than about 99% pure. Within the context of the present disclosure, where a compound comprises stereogenic centers, the term “purified” includes enantiomerically pure compositions and also mixtures of enantiomers or isomers.
[0085] Also within the context of the present disclosure, purified compounds (cannabinoids, terpenes, etc.) may be purposely formulated with other compounds at various levels of purity. Provided that the ingredients used for purposeful formulation are purified prior to the said purposeful formulation, the act of subsequently formulating them does render them not “purified” within the context of an ingredient list.
[0086] In an embodiment, the term “purified” may refer to a cannabinoid that is separated from plant matter from which it was derived. The pure or purified cannabinoid may be contained in solution in a diluent or other medium, or may be a liquid or solid form of the pure cannabinoid absent any diluent.
[0087] In select embodiments of the compositions disclosed herein, the at least one cannabinoid may be a synthetic or semi-synthetic cannabinoid.
[0088] In select embodiments of the compositions disclosed herein, the at least one cannabinoid may be introduced in the form of a cannabis concentrate. As used herein, “cannabis concentrate” is meant to refer a concentrated composition of cannabinoids, such as a cannabinoid extract from a plant. Non-limiting exemplary embodiments of a cannabis concentrate include a full spectrum extract, a broad spectrum extract, a cannabis distillate, a cannabis oil, or any other type of extract containing one or more cannabinoids. In an embodiment, the cannabis concentrate is a cannabis distillate.
[0089] In select embodiments, the compositions may include up to about 35% by weight cannabinoid, more particularly up to about 25% by weight cannabinoid, and more particularly still up to about 15% by weight cannabinoid. In select embodiments, the compositions may include between about 0.1% and about 25% by weight cannabinoid. In an embodiment, the compositions may include between about 5% and about 15% by weight, and more particularly between about 10% and about 15% by weight cannabinoid. In select embodiments, the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight of cannabinoid. [0090] Terpenes
[0091] In an embodiment, the compositions of the present disclosure comprise at least one terpene. In such embodiments, the compositions may comprise a single cannabinoid (e.g. beta-caryophyllene or another terpene) or may comprise any combination of two or more cannabinoids (e.g. beta-caryophyllene and linalool). The compositions may also comprise at least one cannabinoid in combination with the at least one cannabinoid.
[0092] Within the context of this disclosure, the term “terpene” includes cannabis derived terpenes and non-cannabis derived terpenes. Within the context of this disclosure, the term “terpene” also includes terpeoinds. Thus, the reference to “at least one terpene” encompasses and means “at least one terpene and/or terpenoid”. In an embodiment, the compositions herein may comprise at least one terpene and/or terpenoid. In an embodiment, the product containing the compositions herein may comprise at least one terpene and/or terpenoid.
[0093] Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, and by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeteria. Terpenes are also major constituents of Cannabis sativa plants. They often have a strong odor and may protect the plants that produce them by deterring herbivores and by attracting predators and parasites of herbivores. The difference between terpenes and terpenoids is that terpenes are hydrocarbons, whereas terpenoids contain additional functional groups.
[0094] They are the major components of resin, and of turpentine produced from resin. The name "terpene" is derived from the word "turpentine". In addition to their roles as end-products in many organisms, terpenes are major biosynthetic building blocks within nearly every living creature. Steroids, for example, are derivatives of the triterpene squalene.
[0095] When terpenes are modified chemically, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Some authors will use the term terpene to include all terpenoids. Terpenoids are also known as isoprenoids. [0096] Within the context of this disclosure, the term “terpene” includes hemiterpenes, monoterpenols, terpene esters, diterpenes, monoterpenes, polyterpenes, tetraterpenes, terpenoid oxides, sesterterpenes, sesquiterpenes, norisoprenoids, or their derivatives, as well as isomeric, enantiomeric, or optically active derivatives.
[0097] Derivatives of terpenes include terpenoids, hemiterpenoids, monoterpenoids, sesquiterpenoids, sesterterpenoid, sesquarterpenoids, tetraterpenoids, triterpenoids, tetraterpenoids, polyterpenoids, isoprenoids, and steroids. These derivatives are encompassed herein by the term “terpene”, unless specifically stated otherwise.
[0098] Within the context of this disclosure, the term terpene includes the a- (alpha), p- (beta), y- (gamma), oxo-, isomers, or any combinations thereof.
[0099] Terpenes are the primary constituents of the essential oils of many types of plants and flowers. Essential oils are used widely as fragrances in perfumery, and in medicine and alternative medicines such as aromatherapy. Synthetic variations and derivatives of natural terpenes also greatly expand the variety of aromas used in perfumery and flavours used in food additives.
[00100] Higher amounts of terpenes are released by trees in warmer weather, acting as a natural form of cloud seeding. The clouds reflect sunlight, allowing the forest to regulate its temperature. The aroma and flavour of hops comes, in part, from sesquiterpenes (mainly alpha-humulene and beta-caryophyllene), which affect beer quality. Accordingly, in some embodiments, the compositions of the present disclosure may include hop-derived terpenes such as hop-derived terpene blends available as Aramis, Brewer's Gold, Bravo and the like, and combinations thereof.
[00101] Plant terpenes are used extensively for their aromatic qualities and play a role in traditional herbal remedies. Terpenes contribute to the scent of eucalyptus, the flavours of cinnamon, cloves, and ginger, the yellow colour in sunflowers, and the red colour in tomatoes.
[00102] Non-limiting examples of terpenes within the context of this disclosure include: 7,8-dihydro-alpha-ionone, 7,8-dihydro-beta-ionone, Acetanisole, Acetic Acid, Acetyl Cedrene, Anethole, Anisole, Benzaldehyde, Bergamotene (Alpha-cis-Bergamotene) (Alpha- trans-Bergamotene), Bisabolol (Beta-Bisabolol), Alpha Bisabolol, Borneol, Bornyl Acetate, Butanoic/ Butyric Acid, Cadinene (Alpha-Cadinene) (Gamma-Cadinene), Cafestol, Caffeic acid, Camphene, Camphor, Capsaicin, Carene (Delta-3-Carene), Carotene, Carvacrol, Dextro-Carvone, Laevo-Carvone, Alpha-Caryophyllene, Beta-Caryophyllene, Caryophyllene oxide, Cedrene (Alpha-Cedrene) (Beta-Cedrene), Cedrene Epoxide (Alpha-Cedrene Epoxide), Cedrol, Cembrene, Chlorogenic Acid, Cinnamaldehyde, Alpha-amyl- Cinnamaldehyde, Alpha-hexyl-Cinnamaldehyde, Cinnamic Acid, Cinnamyl Alcohol, Citronellal, Citronellol, Cryptone, Curcumene (Alpha-Curcumene) (Gamma-Curcumene), Decanal, Dehydrovomifoliol, Diallyl Disulfide, Dihydroactinidiolide, Dimethyl Disulfide, Eicosane/lcosane, Elemene (Beta-Elemene), Estragole, Ethyl acetate, Ethyl Cinnamate, Ethyl maltol, Eucalyptol/1 ,8-Cineole, Eudesmol (Alpha-Eudesmol) (Beta-Eudesmol) (Gamma-Eudesmol), Eugenol, Euphol, Farnesene, Farnesol, Fenchol (Beta-Fenchol), Fenchone, Geraniol, Geranyl acetate, Germacrenes, Germacrene B, Guaia-1 (10),11-diene, Guaiacol, Guaiene (Alpha-Guaiene), Gurjunene (Alpha-Gurjunene), Herniarin, Hexanaldehyde, Hexanoic Acid, Humulene (Alpha-Humulene) (Beta-Humulene), Ionol (3- oxo-alpha-ionol) (Beta-Ionol), Ionone (Alpha-Ionone) (Beta-Ionone), Ipsdienol, Isoamyl Acetate, Isoamyl Alcohol, Isoamyl Formate, Isoborneol, Isomyrcenol, Isopulegol, Isovaleric Acid, Isoprene, Kahweol, Lavandulol, Limonene, Gamma-Linolenic Acid, Linalool, Longifolene, Alpha-Longipinene, Lycopene, Menthol, Methyl butyrate, 3-Mercapto-2- Methylpentanal, Mercaptan/Thiols, Beta-Mercaptoethanol, Mercaptoacetic Acid, Allyl Mercaptan, Benzyl Mercaptan, Butyl Mercaptan, Ethyl Mercaptan, Methyl Mercaptan, Furfuryl Mercaptan, Ethylene Mercaptan, Propyl Mercaptan, Thenyl Mercaptan, Methyl Salicylate, Methylbutenol, Methyl-2-Methylvalerate, Methyl Thiobutyrate, Myrcene (Beta- Myrcene), Gamma-Muurolene, Nepetalactone, Nerol, Nerolidol, Neryl acetate, Nonanaldehyde, Nonanoic Acid, Ocimene, Octanal, Octanoic Acid, P-Cymene, Pentyl butyrate, Phellandrene, Phenylacetaldehyde, Phenylethanethiol, Phenylacetic Acid, Phytol, Pinene, Beta-Pinene, Propanethiol, Pristimerin, Pulegone, Quercetin, Retinol, Rutin, Sabinene, Sabinene Hydrate, cis-Sabinene Hydrate, trans-Sabinene Hydrate, Safranal, Alpha-Selinene, Alpha-Sinensal, Beta-Sinensal, Beta-Sitosterol, Squalene, Taxadiene, Terpin hydrate, Terpineol, Terpine-4-ol, Alpha-Terpinene, Gamma-Terpinene, Terpinolene, Thiophenol, Thujone, Thymol, Alpha-Tocopherol, Tonka Undecanone, Undecanal, Valeraldehyde/Pentanal, Verdoxan, Alpha-Ylangene, Umbelliferone, or Vanillin.
[00103] In select embodiments, the compositions disclosed herein comprise a terpene selected from p-caryophyllene, caryophyllene oxide, borneol, 1 ,8-cineole, camphene, humulene (e.g., a-humulene), limonene (e.g., D-limonene, L-limonene), linalool, hexyl acetate, myrcene (e.g., 3-myrcene), nerolidol, pulegone, isopulegol, a-pinene, 3-pinene, para-cymene, eugenol, farnesol, geraniol, phytol, terpinene (e.g., gammaterpinene), terpineol (e.g., a-terpineol) and terpinolene, or any combination thereof.
[00104] In select embodiments, the compositions disclosed herein comprise p-caryophyllene as at least one of the terpenes.
[00105] In an embodiment, in the compositions and/or products herein, each of the at least one terpenes have a particle size diluted in water of between about 100 nm and about 110 nm, with a polydispersity of 0.1 or less.
[00106] In particularly suitable embodiments, the compositions include terpenes and/or terpenoids having antimicrobial properties. Exemplary antimicrobial terpenes include, for example, Ocimum basilicum (basil), Laurus nobilis (bay), Cinnamomum verum (Ceylon cinnamon), Capsicum annuum (paprika), Syzygium aromaticum (clove), Mentha piperita (peppermint), Tanacetum vulgare (tansy), Artemisia dracunculus (Tarragon), and the like as known in the art.
[00107] In select embodiments of the compositions disclosed herein, the at least one terpene may be introduced in the form of a pure or purified terpene. As used herein, the term “purified” or “pure” means extracted, isolated, and/or separated from other compounds, formulations, compositions, matter, and/or mass resulting in a greater than 60% purity. A non-limiting example of a purified terpene is a terpene isolate.
[00108] In some embodiments a “purified” terpene is greater than about 70% pure, greater than about 75% pure, greater than about 80% pure, greater than about 85% pure, greater than about 90% pure, greater than about 91% pure, greater than about 92% pure, greater than about 93% pure, greater than about 94% pure, greater than about 95% pure, greater than about 96% pure, greater than about 97% pure, greater than about 98% pure, or greater than about 99% pure. Within the context of the present disclosure, where a compound comprises stereogenic centers, the term “purified” includes enantiomerically pure compositions and also mixtures of enantiomers or isomers.
[00109] In an embodiment, the term “purified” may refer to a terpene that is separated from plant matter from which it was derived. The pure or purified terpene may be contained in solution in a diluent or other medium, or may be a liquid or solid form of the pure terpene absent any diluent.
[00110] In select embodiments of the compositions disclosed herein, the at least one terpene may be a synthetic or semi-synthetic terpene.
[00111] In select embodiments of the compositions disclosed herein, the at least one terpene may be introduced in the form of a terpene concentrate. As used herein, “terpene concentrate” is meant to refer a concentrated composition of terpenes, such as a terpene extract from a plant. Non-limiting exemplary embodiments of a terpene concentrate include a terpene distillate, a terpene oil, or any other type of extract containing one or more terpenes. In an embodiment, the terpene concentrate is a terpene distillate.
[00112] In select embodiments, the compositions may include up to about 35% by weight , more particularly up to about 25% by weight terpene, and more particularly still up to about 15% by weight terpene. In select embodiments, the compositions may include between about 0.1% and about 25% by weight terpene. In an embodiment, the compositions may include between about 5% and about 15% by weight, and more particularly between about 10% and about 15% by weight terpene. In select embodiments, the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight of terpene.
[00113] Furthermore, in some embodiments, the compositions may include a total terpene concentration (relative to the concentration of cannabinoids) beyond what would normally be found in the cannabis flower, allowing for the potential of entourage effects. As used herein, the “entourage-effect” refers to the residual effect of one or more compounds (e.g., cannabinoids, terpenes) of the compositions in the ultimately administered end products.
[00114] As described in greater detail elsewhere herein, in addition to the cannabinoids and/or terpenes, the compositions of the present disclosure may also include additives, such as for example flavonoids, encapsulation materials, and the like and combinations thereof. [00115] In an embodiment, the additives (e.g. flavonoids and/or encapsulation materials) are independently or in combination derived from natural sources and are selected to be stable in the selected compositions, dosage forms, beverages or foodstuffs herein.
[00116] Saccharides
[00117] The compositions disclosed herein comprise at least one saccharide. The at least one saccharide may be a naturally occurring saccharide, a synthetic saccharide, or a combination thereof.
[00118] In an embodiment, the saccharide is a carbohydrate. As used herein, the term “carbohydrate” refers to a compound consisting of carbon, hydrogen, and oxygen atoms. In an embodiment, the carbohydrate has the formula CnH2nOn, wherein n is an integer. In an embodiment, the saccharide may be a modified carbohydrate that includes one or more atoms other than carbon, hydrogen, and oxygen.
[00119] The saccharide may be a monosaccharide, a disaccharide, oligosaccharide, a polysaccharide, or any combination thereof. While a disaccharide contains two monosaccharide units, there is overlap between an oligosaccharide and a polysaccharide. An oligosaccharide is typically considered to contain a small number of monosaccharide units (e.g. 2-20 units, and more particularly 3-10 units), whereas a polysaccharide is typically considered to contain a large number of monosaccharide units, for example more than twenty and often hundreds.
[00120] In an embodiment, the saccharide is a monosaccharide. Monosaccharides are classified by the number of carbon atoms they contain (e.g. triose (3), tetrose (4), pentose (5), hexose (6), and so on). Non-limiting examples of monosaccharides include glucose (dextrose), fructose, galactose, xylose, ribose, and inositol (e.g. myo-inositol). In a particular embodiment, the monosaccharide is inositol. In another particular embodiment, the monosaccharide is myo-inositol. Myo-inositol, or (1R,2S,3R,4R,5S,6s)-cyclohexane- 1 ,2,3,4,5,6-hexol, is a sugar alcohol that can also be made naturally in humans from glucose. [00121] In some embodiments, the saccharide is a disaccharide. Non-limiting examples of disaccharides include sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, and chitobiose.
[00122] In an embodiment, the saccharide is an oligosaccharide. Non-limiting examples of oligosaccharides include raffinose, stachyose, and verbascose. Various classes of oligosaccharides exist, including without limitation, fructooligosaccharides and galactoooligosaccharides.
[00123] In an embodiment, the saccharide is a polysaccharide. Non-limiting examples of polysaccharides include inulin, pectin, amylopectin, beta-glucan, glycogen, and maltodextrin.
[00124] In an embodiment, the at least one saccharide is glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta glucan, glycogen, maltodextrin, or any combination thereof.
[00125] In some embodiments, the at least one saccharide is inulin. Inulin (C6nHi0n+2O5n+i) is a heterogeneous mixture of fructose polymers typically extracted from chicory. Other exemplary natural sources of inulin include asparagus, garlic, artichoke, jicama, onions, and yacon root. Inulin consists of a chain-terminating glucose moiety and repetitive fructosyl moieties, which are linked by p-(2^>1 ) bonds. The degree of polymerization for inulin ranges from 2-60. Inulin may be obtained from any number of plant sources, and may also be modified or manufactured. Oligofructose is a subgroup of inulin made by removing the longer molecules. Typically, oiligofructose comprises fructose molecules of between two to ten units. High-performance (HP) inulin is a subgroup of inulin made by removing the shorter molecules. Typically, HP inulin comprises fructose molecules of between 11 to 60 units, with an average degree of polymerization typically around 25. Fructooligosaccharides are a subgroup of inulin consisting of short inulin molecules synthesized from table sugar.
[00126] In another embodiment, the at least one saccharide is inositol.
[00127] In another embodiment, the at least one saccharide is myo-inositol. [00128] In another embodiment, the at least one saccharide is a combination of inositol and inulin. In another embodiment, the at least one saccharide is a combination of myo-inositol and inulin.
[00129] Within the context of this disclosure, the term “saccharide” may also refer to a number of naturally occurring or synthetic compounds that are saccharide derivatives, such as saccharide substitutes. Non-limiting examples of saccharide substitutes may include sorbitol, stevia, mannitol, aspartame, sucralose, isomalt, and xylitol.
[00130] In an embodiment, a combination of saccharides may be used in the compositions disclosed herein. When more than one saccharide is used, they may be used at any amount relative to the other. In an embodiment, the first saccharide and the second saccharide may be used at a ratio between 20:1 and 1 :20, between 15:1 and 1 :15, between 10:1 and 1 :10, or between 5:1 and 1 :5 by weight to each other. In an embodiment, the two saccharides may be used at about a 4:1 , 3:1 , 2:1 , 1 :1 , 1 :2, 1 :3 or 1 :4 by weight ratio to each other. In an embodiment, the two saccharides may be used at about a 1 :1 by weight ratio to each other.
[00131] In select embodiments, the compositions may include up to about 85% by weight saccharide, more particularly up to about 75% by weight saccharide, and more particularly still up to about 60% by weight saccharide. In select embodiments, the compositions may include between about 25% and about 85% by weight saccharide. In an embodiment, the compositions may include between about 35% and about 75% by weight, more particularly between about 50% and about 70% by weight, and more particularly still between about 55% and about 65% by weight saccharide. In select embodiments, the compositions may include about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, or about 70% by weight saccharide.
[00132] Surfactants
[00133] The compositions herein comprise at least one surfactant. In some embodiments, the surfactant is a non-ionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, or any combination thereof. In some embodiments, the surfactant may be a natural surfactant. As used herein, the term “natural surfactant” is intended to refer to a surfactant obtained from a natural source. [00134] The term “non-ionic surfactant” typically refers to a surfactant without an electrical charge. Non-limiting examples of non-ionic surfactants include partial fatty acid esters, fatty alcohols, sterols, polyethylene glycols, such as ethoxylated fatty acids, ethoxylated fatty alcohols, and ethoxylated sorbitan esters, sugar emulsifiers, polyglycerol emulsifiers, and silicon emulsifiers.
[00135] The term “anionic surfactant” typically refers to a surfactant having a negative charge at the hydrophilic end. Non-limiting examples of anionic surfactants include soaps, such as sodium stearate, fatty alcohol sulfates, mono, di- and tri-alkyl phosphoric acid esters and the ethoxylates thereof, fatty acid lactate esters, fatty acid citrate esters, and fatty acid citroglycerin esters.
[00136] The term “cationic surfactant” typically refers to a surfactant having a positive charge. Non-limiting examples of cationic surfactants include quaternary ammonium compounds having a long-chain aliphatic group, such as distearyldimonium chloride.
[00137] The term “amphoteric surfactant” typically refers to a surfactant having both an anionic and a cationic hydrophilic group (i.e. both a negative and a positive charge). Non-limiting examples of amphoteric surfactants include alkylamininoalkane carboxylic acids, betaines, sulfobetaines, and imidazoline derivatives.
[00138] In some embodiments, the non-ionic surfactant may be a partial fatty acid ester, a fatty acid ester of glycerol (e.g. glycerol monostearate, glycerol monolaurate), a fatty alcohol, a sterol, a polyethylene glycol, an ethoxylated fatty acid (e.g. oleic acid ethoxylate, stearic acid ethoxylate, coconut fatty acid ethoxylate, lauric acid ethoxylate, and myristic/palmitic acid ethoxylate), an ethoxylated fatty alcohol (e.g. octaethylene glycol monododecyl ether, pentaethylene glycol monododecyl ether), a sorbitan ester, an ethoxylated sorbitan ester, an ethoxylated amines or fatty acid amide (e.g. polyethoxylated tallow amine, cocamide monoethanolamine, and cocamide diethanolamine), a polyglycerol, a polglyceryl ester (monoester and multi-ester), or any combination thereof.
[00139] Non-limiting examples of sorbitan esters include Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, or any combination thereof. In an embodiment, the surfactant may be an ethoxylated sorbitan ester, such as for example Tween 20, Tween 40, Tween 45, Tween 60, Tween 65, Tween 80, Tween 81 , Tween 85, or any combination thereof. [00140] Non-limiting examples of polyglyceryl esters include Polyglyceryl-4 Caprate, Polyglyceryl-4 Caprylate, Polyglyceryl-4 Isostearate, Polyglyceryl-4 Laurate, Polyglyceryl-4, Oleate, Polyglyceryl-5 Dioleate, Polyglyceryl-5 Isostearate, Polyglyceryl-5 Laurate, Polyglyceryl-5 Myristate, Polyglyceryl-5 Oleate, Polyglyceryl-5 Stearate, Polyglyceryl-5 Triisostearate, Polyglyceryl-5 Trioleate, Polyglyceryl-6 Dioleate, Polyglyceryl-6 Distearate, Polyglyceryl-6 Isostearate, Polyglyceryl-6 Octastearate, Polyglyceryl-6 Oleate, Polyglyceryl- 6 Pentastearate, Polyglyceryl-6 Stearate, Polyglyceryl-6 Tricaprylate, Polyglyceryl-8 Decaerucate/Decaisostearate/Decaricinoleate, Polyglyceryl-8 Oleate, Polyglyceryl-8 Stearate, Polyglyceryl-10 Behenate/Eicosadioate, Polyglyceryl-10 Caprylate/Caprate, Polyglyceryl-10 Decaisostearate, Polyglyceryl-10 Decaoleate, Polyglyceryl-10 Diisostearate, Polyglyceryl-10 Dioleate, Polyglyceryl-10 Dipalmitate, Polyglyceryl-10 Distearate, Polyglyceryl-10 Heptahydroxystearate, Polyglyceryl-10 Hydroxystearate/Stearate/Eicosadioate and Polyglyceryl-10 Fatty Ester (POLYALDO® 10-2-P), Polyglyceryl-10 Isostearate, Polyglyceryl-10 Laurate, Polyglyceryl-10 Linoleate, Polyglyceryl-10 Myristate, Polyglyceryl-10 Nonaisostearate, Polyglyceryl-10 Oleate, Polyglyceryl-10 Palmitate, Polyglyceryl-10 Pentahydroxystearate, Polyglyceryl-10 Pentaisostearate, Polyglyceryl-10 Pentaoleate, Polyglyceryl-10 Pentastearate, Polyglyceryl-10 Stearate, Polyglyceryl-10 Tristearate, or any combination thereof.
[00141] In some embodiments, the anionic surfactant may be sodium stearate, an alkyl sulfate (e.g. ammonium lauryl sulfate, sodium lauryl sulfate, sodium dodecyl sulfate), an alkyl-ether sulfate (e.g. sodium lauryl ether sulfate, Sodium myreth sulfate), a fatty alcohol sulfate, a mono, di- and tri-alkyl phosphoric acid ester or an ethoxylate thereof, a fatty acid lactate ester, a fatty acid citrate ester, a fatty acid citro-glycerin ester, or any combination thereof.
[00142] In some embodiments, the cationic surfactant may be a quaternary ammonium compound having a long-chain aliphatic group (e.g. cetrimonium bromide, cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, dimethyldioctadecylammonium chloride, dioctadecyldimethylammonium bromide, or any combination thereof.
[00143] In some embodiments, the amphoteric surfactant may be an alkylamininoalkane carboxylic acid, a betaine (e.g. cocamidopropyl betaine), a sulfobetaine, or an imidazoline derivative. [00144] In some embodiments, the at least one surfactant comprises a natural surfactant. Exemplary embodiments of natural surfactants include, without limitation, surfactants comprising saponins, a lecithin, gum arabic, or a sterol.
[00145] Saponins are naturally occurring compounds that are found in a wide variety of plants (e.g. legumes), and are also produced by some lower marine animals and some bacteria. In the context of the present disclosure, the surfactant may comprise saponins from any suitable source. For example, and without limitation, the saponins may be from Quillaja, Soapwort (Saponaria), Quinoa (Chenopodium), Soap nut (Sapindus), Soapweed (Yucca), Soapbush (Alphitonia), Soaproot (Chlorogallum), Buffaloberry (Shepherdia), or any combination thereof.
[00146] In an embodiment, the surfactant comprises Quillaja saponins. The surfactant comprising Quillaja saponins may be from any suitable source. As will be appreciated, Quillaja saponins may be derived from a Quillaja tree, such as for example a Quillaja saponaria tree or a Quillaja brasiliensis tree. In a particular embodiment, the surfactant comprising Quillaja saponins is derived from a Quillaja saponaria tree. In an embodiment, the surfactant comprising Quillaja saponins is a Q-NATURALE® surfactant (Ingredion Incorporated, USA), a Saponin from Quallaja Bark (such as for example supplied by Sigma Aldrich, USA), Saponin Quillaja sp. (Sigma Aldrich, USA), a Quillaja extract (such as for example Quillaja extract E 999;), purified Quillaja saponins (e.g. from Sigma Aldrich, USA), a modified Quillaja extract, or combinations thereof.
[00147] In an embodiment, the surfactant comprising Quillaja saponins is a Q-NATURALE® surfactant. In an embodiment, the Q-NATURALE® surfactant comprises Q-NATURALE® 200, Q-NATURALE® 200V, or a combination thereof.
[00148] In an embodiment, the Q-NATURALE® surfactant is Q-NATURALE® 200. Q-NATURALE® 200 is described as a natural emulsifier extracted from Quillaja trees and comprising about 65-75% saponin (dry basis) (Ingredion Incorporated, USA). However, modifications and alterations to Q-NATURALE® 200 are also encompassed herein.
[00149] In an embodiment, the Q-NATURALE® surfactant is Q-NATURALE® 200V. Q-NATURALE® 200V is described as a naturally-derived liquid emulsifier derived from the Quillaja Saponaria Molina tree comprising about 13-16% Saponin (wet basis) (Ingredion Incorporated, USA). However, modifications and alterations to Q-NATURALE® 200V are also encompassed herein.
[00150] Lecithin is a term commonly used to describe a group of fatty acid substances found in plant and animal tissues. Exemplary sources of lecithin include, without limitation, lecithin which is found in egg-yolks and milk, as well as being extracted from soy beans (i.e. soy lecithin), sunflower (i.e. sunflower lecithin), canola (i.e. canola lecithin), rapeseed (i.e. rapeseed lecithin), cottonseed (i.e. cottonseed lecithin), marine sources, and animal fats. Lysolecithins may also be used as a surfactant in the compositions disclosed herein.
[00151] Any type of lecithin may be used in the practice of the present disclosure. In an embodiment, the lecithin is a soy lecithin, sunflower lecithin, canola lecithin, rapeseed lecithin, cottonseed lecithin, or any combination thereof. In a particular embodiment, the lecithin is a soy lecithin. In an embodiment, the lecithin is a sunflower lecithin.
[00152] In an embodiment, the lecithin is a purified lecithin such as, for example, Lipoid S 40, Lipoid H 50, Lipoid PHOSAL® 50 SA, Lipoid PHOSAL® 53 MCT, Lipoid P 75, Lipoid S 75, Lipoid S 80, Lipoid E 80, PHOSPHOLIPON® 85 G, Lipoid PHOSPHOLIPON® 90 G, Lipoid PHOSPHOLIPON® 90 H, Lipoid H 100, or any combination thereof.
[00153] In an embodiment, the lecithin is of the ALCOLEC® family of lecithins (e.g. ALCOLEC® F-100, ALCOLEC® EM, ALCOLEC® S, ALCOLEC® BS, ALCOLEC® HL, ALCOLEC® H 20, ALCOLEC® EXTRA-A, ALCOLEC® E 35, ALCOLEC® E 60 or ALCOLEC® HR), including deoiled soy lecithin.
[00154] Sterol is an organic compound of the formula C17H28O. It contains the gonane structure with replacement of a hydrogen atom in position 3 with a hydroxyl group. Thus, it is an alcohol of gonane. Sterol occurs naturally in most eukaryotes, including plants, animals, and fungi. Sterol surfactant include, without limitation, sterol ethoxylates and sterol glucosides.
[00155] In some embodiments, the surfactant may be a polyglyceryl surfactant, and/or a long chain PEG surfactant. In some embodiments, the surfactant may be glyceryl laurate, glyceryl stearate citrate, or derivatives thereof. [00156] In some embodiments, the surfactant may comprise polyglycol ized glycerides, polyoxyethylene glycerides, polyethylene glycol-fatty acid esters, polyethylene glycol glycerol fatty acid esters, transesterfication products of oils and alcohols, polyglycerized fatty acids, glycerol fatty acid esters, polyglycerol fatty acid esters, propylene glycol fatty acid esters, mono- and di-glycerides, polyethylene glycol sorbitan fatty acid esters, polyoxyethylene- polyoxypropylene block copolymers, sorbitan fatty acid esters, d-a-tocopheryl polyethylene glycol 1000 succinate, polyoxyethyleneglycol 660 12-hydroxystearate, polysorbates, or any combination thereof.
[00157] In some embodiments, the surfactant may comprise almond oil PEG-6 esters, almond oil PEG-60 esters, apricot kernel oil PEG-6 esters, caprylic/capric triglycerides PEG-4 esters, caprylic/capric glycerides PEG-6 esters, caprylic/capric glycerides PEG-8 esters, castor oil PEG-50 esters, hydrogenated castor oil PEG-5 esters, hydrogenated castor oil PEG-7 esters, hydrogenated castor oil PEG-9 esters, corn oil PEG-6 esters, corn oil PEG-8 esters, corn glycerides PEG-60 esters, olive oil PEG-6 esters, hydrogenated palm/palm kernel oil PEG-6 esters, hydrogenated palm/palm kernel oil PEG-6 esters with palm kernel oil and PEG-6 and palm oil, palm kernel oil PEG-40 esters, peanut oil PEG-6 esters, glycerol esters of saturated C8-C18 fatty acids, glyceryl esters of saturated C12-C18 fatty acids, glyceryl laurate/PEG-32 laurate, glyceryl laurate glyceryl/PEG 20 laurate, glyceryl laurate glyceryl/PEG 32 laurate, glyceryl, laurate glyceryl/PEG 40 laurate, glyceryl oleate/PEG-20 glyceryl, glyceryl oleate/PEG-30 oleate, glyceryl palmitostearate/PEG-32 palmitostearate, glyceryl stearate/PEG stearate, glyceryl stearate/PEG-32 stearate, saturated polyglycolized glycerides, triisostearin PEG-6 esters, triolein PEG-6 esters, trioleate PEG-25 esters, polyoxyl 35 castor oil, polyoxyl 40 hydrogenated castor oil, polyoxyl 60 hydrogenated castor oil, PEG-8 caproate, PEG-8 caprylate, PEG-8 caprate PEG-8 laurate, PEG-8 oleate, PEG- 8 stearate, PEG-9 caproate, PEG-9 caprylate, PEG-9 caprate PEG-9 laurate, PEG-9 oleate, PEG- 9 stearate, PEG-10 caproate, PEG-10 caprylate, PEG-10 caprate PEG-10 laurate, PEG-10 oleate, PEG-10 stearate, PEG-10 laurate, PEG- 12 oleate, PEG- 15 oleate, PEG-20 laurate, PEG-20 oleate, caprylate/caprate diglycerides, glyceryl monooleate, glyceryl ricinoleate, glyceryl laurate, glyceryl dilaurate, glyceryl dioleate, glyceryl mono/dioleate, glyceryl caprylate/caprate, medium chain (C8/C10) mono- and diglycerides, mono-and diacetylated monoglycerides, polyglyceryl oleate, polyglyceryl-2 dioleate, poly glyceryl- 10 trioleate, poly glyceryl- 10 laurate, polyglyceryl-10 oleate, polyglyceryl- 10 mono dioleate, propylene glycol caprylate/caprate, propylene glycol dicaprylate/ dicaprate, propylene glycol monolaurate, propylene glycol ricinoleate, propylene glycol monooleate, propylene glycol dicaprylate/dicaprate, propylene glycol dioctanoate, PEG-20 sorbitan monolaurate, PEG-20 sorbitan monopalmitate, PEG-20 sorbitan monostearate, PEG-20 sorbitan monooleate, poloxamers (108, 124, 182, 183, 188, 212, 217, 238, 288, 331 , 338, 335, 407), sorbitan monolaurate, sorbitan monopalmitate, sorbitan monoleate, sorbitan monostearate, sorbitan tristearate, D-a-tocopheryl polyethylene glycol 1000 succinate, polysorbate 20, polysorbate, polyethyleneglycol 660 12-hydroxystearate, or any combination thereof.
[00158] In some embodiments, the at least one surfactant may be a Vitamin E TPGS (e.g. Vitamin E TPGS 200, Vitamin E TPGS 300, Vitamin E TPGS 400, Vitamin E TPGS 1000, Vitamin E TPGS 1500, Vitamin E TPGS 2000 and Vitamin E TPGS 4000), Gum Arabic, PURITY GUM® ULTRA, and other like compounds.
[00159] In some embodiments, the surfactant may be a surfactant sold under the trademark Brij™ or ECO Brij™ (Croda, UK). In an embodiment, the surfactant is Polyoxyethylene (10) cetyl ether (Ceteth-10; e.g. Brij™ C10), Polyoxyethylene (20) cetyl ether (Ceteth-20; e.g. Brij™ C20), Polyoxyethylene (20) Cetyl Stearyl Ether (Ceteareth-20; e.g. Brij™ CS20), Alkoxylated ether (lsoceteth-20; e.g. Brij™ IC20); Alkoxylated ether and Aqua (lsocetech-20; e.g. Brij™ IC20-70), Ethoxylated Fatty Alcohol (Laureth-4; e.g. Brij™ L4), Polyoxyethylene (23) lauryl ether (Laureth-23; e.g. Brij™ L23), Polyoxyethylene (23) lauryl ether and Aqua (Laureth-23; e.g. Brij™ L23-69), Polyoxyethylene (10) oleyl ether (Oleth-10; e.g., Brij™ O10), Polyoxyethylene (20) oleyl ether (Oleth-20; e.g. Brij™ 020), Polyoxyethylene (10) stearyl ether (Steareth-10; e.g. Brij™ S10), Polyoxyethylene (20) stearyl ether (Steareth-20; e.g. Brij™ S20), Polyoxyethylene (100) stearyl ether (Steareth- 100; e.g. Brij™ S100), ethoxylated fatty alcohols (Steareth-21 ; e.g. Brij™ S721 ), or any combination thereof. Many of these same or different surfactants are also available under the ECO Brij™ (Croda, UK) line of ‘eco-friendly’ surfactants.
[00160] In an embodiment, the compositions of the present disclosure may comprise a sucrose monoester as a surfactant, alone or in combination with other surfactants. The sucrose monoester may be sucrose monopalmitate, sucrose monolaurate, sucrose monostearate, or any combination thereof. For any one of these embodiments, the sucrose monoester may comprise a small quantity of diester. [00161] In an embodiment, a combination of surfactants may be used in the compositions disclosed herein. When more than one surfactant is used, they may be used at any amount relative to the other. In an embodiment, the first surfactant and the second surfactant may be used at a ratio between 20:1 and 1 :20, between 15:1 and 1 :15, between 10:1 and 1 :10, or between 5:1 and 1 :5 by weight to each other. In an embodiment, the two surfactants may be used at about a 4:1 , 3:1 , 2:1 , 1 :1 , 1 :2, 1 :3 or 1 :4 by weight ratio to each other. In an embodiment, the two surfactants may be used at about a 1 :1 by weight ratio to each other.
[00162] In select embodiments, the compositions may include up to about 30% by weight surfactant, more particularly up to about 20% by weight surfactant, and more particularly still up to about 15% by weight surfactant. In select embodiments, the compositions may include between about 0.5% and about 15% by weight surfactant. In an embodiment, the compositions may include between about 2.0% and about 15% by weight, more particularly between about 3.0% and about 15% by weight surfactant. In select embodiments, the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, or about 15% by weight surfactant.
[00163] Carrier Oils
[00164] The compositions herein comprise at least one carrier oil. In an embodiment, the carrier oil is an “oily medium”. By “oily medium” it is meant to refer to a medium capable of dissolving lipophilic or hydrophobic compounds, such as cannabinoids. Particularly suitable carrier oils include natural oils as known in the art, for example, edible vegetable oils. In some alternative embodiments, the carrier oils can include synthetic edible oils, for example, hydrogenated vegetable oils, medium chain triglyceride (MCT) oils, and the like and combinations thereof.
[00165] A non-limiting list of exemplary carrier oils includes a medium-chain triglyceride (MCT), a long-chain triglyceride (LOT), glycerine/glycerol, a monoglyceride (e.g. glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, Peceol™), Labrasol, Labrafac Lipophile WL 1349, Labrafil M1944, Plural Oliqiue CC 497, Transcutol HP, Tween 20, Tween 40, Tween 45, Tween 60, Tween 65, Tween 80, Tween 81 , Tween 85, Gelucire 48/16, Vitamin E TPGS, and combinations thereof.
[00166] In an embodiment, the at least one carrier oil is an MCT oil. In a non-limiting embodiment, triglycerides in the MCT oil are esters derived from glycerol and three medium-chain fatty acids such as for example caproic acid, caprylic acid, capric acid, lauric acid, or any combination thereof.
[00167] In an embodiment, the at least one carrier oil is an LCT oil. In a non-limiting embodiment, triglycerides in the LCT oil are esters derived from glycerol and three long-chain fatty acids such as for example myristic acid, palmitic acid, stearic acid, arachidic acid, linoleic acid, or any combination thereof.
[00168] In an embodiment, the at least one carrier oil is a coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, sesame oil.
[00169] In an embodiment, the at least one carrier oil is comprised of monoglycerides. The monoglycerides may be of a single type (e.g. glyceryl monolinoleate) or may be a mixture of different types. The monoglycerides may include only the monoglyceride ester, or may include one or both of di- and triglycerides. In some embodiments, the monoglyceride fraction is predominant over the di- and triglyceride components. In some embodiments, the di- or triglyceride fractions may be predominant over the monoglycerides, such as for example in Maisine® CC. In particular embodiment, the carrier oil is Maisine® CC.
[00170] In select embodiments, the compositions may include up to about 25% by weight carrier oil, more particularly up to about 20% by weight carrier oil, and more particularly still up to about 15% by weight carrier oil. In select embodiments, the compositions may include between about 0.5% and about 25% by weight carrier oil. In an embodiment, the compositions may include between about 5% and about 20% by weight, and more particularly between about 10% and about 15% by weight carrier oil. In select embodiments, the compositions may include about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight carrier oil.
[00171] Additives
[00172] In some embodiments, the compositions or products (e.g. beverages, foodstuffs, etc.) of the present disclosure may further include additives, such as for example and without limitation flavonoids, encapsulation materials, other additives (described below), or any combination thereof. Such additives may be used to enhance flavour, viscosity, aroma and the like. Terpenes, as described elsewhere herein, may also be included in the compositions or products of the present disclosure as an additive.
[00173] In an embodiment, the additives may be derived from cannabis plants. In an embodiment, the additives may be derived from natural sources other than a cannabis plant, such as a plant of a different species. Alternatively, in some embodiments, the additives may be synthetic or semi-synthetic compounds.
[00174] Flavonoids
[00175] In some embodiments, the compositions or products (e.g. beverages, foodstuffs, etc.) of the present disclosure may further include additives such as one or more flavonoids.
[00176] As used herein, the term “flavonoid” refers to any compound of a large class of plant pigments having a structure based on or similar to that of flavone. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings and a heterocyclic ring.
[00177] Within the context of this disclosure, the term “flavonoids” includes bioflavonoids, isoflavonoids and neoflavonoids. Isoflavones use the 3-phenylchromen-4- one skeleton (with no hydroxyl group substitution on carbon at position 2). Examples include: Genistein, Daidzein, Glycitein, Isoflavanes, Isoflavandiols, Isoflavenes, Coumestans, and Pterocarpans.
[00178] Within the context of this disclosure, the term “flavonoids” also includes anthocyanidins, anthoxanthins, flavanones, flavanonols and flavens. [00179] Flavonoids are widely distributed in plants, fulfilling many functions.
Flavonoids are the most important plant pigments for flower colouration, producing yellow or red/blue pigmentation in petals designed to attract pollinator animals. In higher plants, flavonoids are involved in UV filtration, symbiotic nitrogen fixation and floral pigmentation. They may also act as chemical messengers, physiological regulators, and cell cycle inhibitors. Some flavonoids have inhibitory activity against organisms that cause plant diseases, e.g. Fusarium oxysporum.
[00180] Sources of flavonoids include, without limitation, cannabis, parsley, blueberries, black tea, citrus, wine, cocoa and peanut.
[00181] Additional exemplary flavonoids for use in the compositions include Apigenin, beta-sitosterol, cannaflavin A, kaempferol, luteolin, orientin, quercetin and combinations thereof.
[00182] In an embodiment, the flavonoid is cannaflavin.
[00183] Encapsulation Materials
[00184] In some embodiments, the compositions or products (e.g. beverages, foodstuffs, etc.) of the present disclosure may include one or more encapsulation materials. A multitude of substances may be used to entrap, coat, or encapsulate materials. In some embodiments, the encapsulation material is one that has been certified for food applications as “generally recognized as safe” (GRAS).
[00185] In an embodiment, the encapsulation material is of plant, marine, animal, or microbial origin. In an embodiment, the encapsulation material is a carbohydrate polymer, a protein, a lipid, or any combination thereof. Exemplary and non-limiting carbohydrate polymers include starch, cellulose, plant exudates, plant extracts, polysaccharide, carrageenan, alginate, xanthan, gellan, dextran, chitosan, or any combination thereof.
Exemplary and non-limiting proteins includes hemp protein, gluten (e.g. corn), pea isolate, soy isolate, caseins, whey proteins, gelatin, or any combination thereof. Exemplary and non-limiting lipids include fatty acids, fatty alcohols, glycerides, waxes, phospholipids, or any combination thereof. In some embodiments, the encapsulation materials form structure such as liposomes, micelles, or the like.
[00186] In select embodiments, the encapsulation material is hemp protein. Reference is made, for example and without limitation, to United States patent application publication no. US 20190335800 in the name of POS Management Corp.
[00187] Other Additives
[00188] In some embodiments, the compositions or products (e.g. beverages, foodstuffs, etc.) of the present disclosure may include any number of other additives, including without limitation a solvent, a bulking agent, an antioxidant, or a nutritional supplement. These components may be used either alone or in combination to improve, for example, the chemical and/or physical properties, stability, nutritional profile, taste, colour and/or viscosity, of the compositions disclosed herein or a beverage or foodstuff produced therefrom. In an embodiment, the antioxidant may be ascorbyl palmitate or a-tocopherol.
[00189] Yet other suitable types of modifiers and additives that may be used in the compositions or products (e.g. beverages, foodstuffs, etc.) disclosed herein include viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners (e.g. liquid sweeteners), and the like and combinations thereof, as known in the beverage and food arts, to provide improved solubility, stability, bioavailability, colour and taste.
[00190] Nutritional supplements comprise substances useful to the consumer of the compositions disclosed herein, or beverages or foodstuffs prepared therewith, for maintenance of normal body health. Non-limiting examples of nutritional supplements may include essential nutrients including vitamins, dietary minerals, amino acids and fatty acids. Exemplary nutritional supplements may include vitamin A, vitamin B1 , vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, vitamin C, vitamin D, vitamin E, vitamin K calcium, phosphorus, potassium, sulfur, sodium, chlorine, magnesium, iron, cobalt, copper, zinc, molybdenum, iodine, selenium, manganese, nickel, chromium, fluorine, boron, strontium histidine, isoleucine, leucine, lysine, methionine, cysteine, phenylalanine, tyrosine, threonine, tryptophan, valine, alpha-linoleic acid, and linoleic acid. [00191] Viscosity modifiers include any compound or agent capable of altering the viscosity of the compositions disclosed herein, or a beverage or foodstuff produced therewith. Exemplary embodiments of viscosity modifiers include anticaking agents, antifoaming agents, bulking agents, coagulation agents, gelling agents, glazing agents, humectants, leavening agents, tenderizers, and thickeners.
[00192] Sweeteners include any compound or agent that is capable of sweetening the taste of the compositions disclosed herein, or a beverage or foodstuff produced therewith. The sweetener may be a natural sweetener or an artificial sweetener. The sweetener may be a solid, liquid or semi-liquid. Exemplary embodiments of sweeteners include sugars and sugar alcohols, and more particularly stevia, erythritol, and xylitol. In an embodiment, the sweetener may be a liquid sugar solution, such as without limitation those having a Brix value of about 67.5 °Bx. In an embodiment, the sweetener may be an Isocane 67.5 °Bx liquid sugar solution.
[00193] METHODS OF PREPARING THE COMPOSITIONS
[00194] In an embodiment, to prepare the compositions of the present disclosure at least one cannabinoid and/or terpene, at least one surfactant, at least one saccharide, and at least one carrier oil are mixed, in any order.
[00195] In a particular embodiment, methods for preparing the compositions disclosed herein comprise: combining at least one cannabinoid and/or terpene with at least one carrier oil to dissolve the cannabinoid in the carrier oil; separately preparing an aqueous solution comprising at least one saccharide; adding to the aqueous saccharide solution the cannabinoid and/or terpene/carrier oil solution and at least one surfactant; homogenizing and optionally subjecting the mixture to one or more passes through a microfluidizer; and spray drying the mixture to provide a solid powder.
[00196] During the step of combining the cannabinoid and/or terpene with the carrier oil, heat may be applied. In an embodiment, the combining is performed under heated conditions of between about 40°C and about 75°C. The cannabinoid and/or terpene and carrier oil may be combined with mixing or stirring, for example with a stir bar.
[00197] During the step of preparing an aqueous solution comprising the saccharide, heating may also be applied to assist in dissolving the saccharide. In an embodiment, the heated conditions are between about 25°C and about 75°C. The solution may be mixed to aid in complete solubilization of the saccharide, for example with a stir bar.
[00198] In the step of adding to the aqueous saccharide solution the cannabinoid and/or terpene /carrier oil solution and at least one surfactant, the components may be added in any order. In a particular embodiment, the at least one surfactant is added and mixed into the aqueous saccharide solution before adding the cannabinoid and/or terpene/carrier oil solution. The solutions may be kept warm (e.g. between about 25°C and about 75°C) during this step. Also, mixing/stirring may be performed throughout this step to obtain a homogenous and uniform emulsion. Optionally, during this step, a minimal amount of ethanol may be used to dissolve and transfer any residual cannabinoid/carrier oil solution left behind in the beaker or container in which it was prepared.
[00199] After this, the mixture can optionally be passed one or more times through a microfluidizer, for example to create an emulsion system with small particles.
[00200] Further, if any additives as described above are to be included in the composition, it may be suitable to mix the additives at any stage in any order. In an embodiment, the additives may be added into either the aqueous saccharide solution or the cannabinoid and/or terpene/carrier oil prior to combining these solutions.
[00201] A product may be prepared by mixing the powder composition with an aqueous solution or a foodstuff. In an embodiment, the product is a beverage. In an embodiment, the product is a sports drink beverage. A product may also be prepared by first forming a liquid emulsion using the powder composition, and then adding the liquid emulsion to the beverage liquid or other foodstuff.
[00202] Further, if any additives as described herein are to be included in the product, it is suitable to mix the additives into the product at the appropriate stage. For example, in an embodiment, the product may comprise one or more of: terpenes, terpenoids, flavonoids, viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners, and combinations thereof. [00203] PRODUCTS INCLUDING THE COMPOSITIONS
[00204] The present disclosure is further directed to using the compositions disclosed herein to form end use products such as ingestibles and topical solids and liquids. The ingestibles can include, for example, beverages, liquids and foodstuffs.
[00205] Thus, the compositions of the present disclosure may be used in the preparation of foodstuffs and beverages. As used herein, a beverage is any drink that may be consumed by a subject. A foodstuff is any substance suitable for consumption as a food.
[00206] The compositions may be combined with any beverage-compatible or food-compatible ingredient. For example, compositions of the present disclosure may be used directly in the preparation of foodstuffs and beverages, e.g. as an additive or ingredient. Powder compositions may be used either directly, e.g. as an additive or ingredient, or indirectly e.g. by first dissolving the powder in a solvent (e.g. water) to form a liquid composition prior to use. In some embodiments, the powder compositions may be added to beverage or foodstuff directly. In other embodiments, the powder compositions are diluted with a bulking agent. The pre-bulked and/or bulked powder compositions can be packaged for individual servings (e.g. sachets/packets), packages in bulk within a single container, or a combination thereof.
[00207] When used in beverages, water-soluble compositions of the present disclosure may be added to a beverage liquid. Generally, beverage liquids are liquids meeting the common meaning of the term "biocompatible", which include materials that are not harmful to living tissue. Suitably, such beverage liquids comprise water, oil, alcohol; with or without additives or modifiers or both. Such beverage liquids can be divided into various groups such as plain/stil I water, carbonated water, alcohol, non-alcoholic drink, soft drinks, electrolyte drinks (e.g. sports drink beverages), fruit juice, vegetable juice, tea, coffee, milk, or other hot, room temperature or cold liquids used in drinks. Beverages can be caffeinated or non-caffeinated and may contain calories or not. Such beverages may be produced in ready to use form or be produced in a form suitable for preparation in final consumable form at or proximate to the time of ingestion.
[00208] Typically, beverage liquids will make up between about 50% and 99.99% by weight or by volume of the beverage. In an embodiment, beverage liquids will make up between about 60% and about 99.99% by weight or by volume of the beverage, more particularly between about 70% and about 99.99% by weight or by volume of the beverage, more particularly still between about 80% to about 99.99% by weight or by volume of the beverage, and even more particularly still between about 80% to about 99.99% by weight or by volume of the beverage. In an embodiment, the beverage liquid will make up between about 80% and about 99.99% by weight of the beverage. In an embodiment, the beverage liquid will make up between about 80% and about 99.9% by weight of the beverage, between about 80% and about 99%, or between about 80% and about 90% by weight of the beverage. In an embodiment, the beverage liquid will make up between about 95% and about 99.9% by weight of the beverage. In an embodiment, the beverage liquid will make up about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99%, or more by weight of the beverage. In an embodiment, the beverage liquid will make up about 99.0%, about 99.1%, about 99.2%, about 99.3%, about 99.4%, about 99.5%, about 99.6%, about 99.7%, about 99.8%, or about 99.9% by weight of the beverage. In an embodiment, the beverage liquid is water. In an embodiment, additives may be present in addition to the quantity of beverage liquid. In an embodiment, a liquid additive (e.g. sweetener) may be present in addition to the quantity of beverage liquid.
[00209] In a particular embodiment, the beverage liquid will make up between about 80% and about 95% by weight of the beverage, and a liquid additive (e.g. sweetener) will make up between about 4.9% and about 14.9% by weight of the beverage. In select embodiments, the beverage liquid will make up about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95% by weight of the beverage. In select embodiments, a liquid additive (e.g. sweetener) will make up about 18%, about 17%, about 16%, about 15%, about 14%, about 13%, about 12%, about 11%, about 10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about 3% or less by weight of the beverage. In an embodiment, the beverage liquid is water and the liquid additive is a liquid sweetener, such as for example a 67.5 °Bx (Brix) sugar solution.
[00210] Non-limiting examples of beverages that may be prepared with the compositions of the present disclosure include but are not limited to: hot and cold beverages including water, fruit juice, vegetable juice, tea, coffee, softs drinks, sports drinks, energy drinks, alcohol, flavoured water, or single-serve beverage cartridges. Non-limiting examples of foodstuffs include baked goods (e.g. cookies, brownies, cake, pie, biscuits and pastries), candies (e.g. hard candy, soft candy, gummies, etc.), chocolates, lozenges, gum, mints, dried fruits, nuts, granola, truffles, caramels, chews, taffy, prepared meals, cooking ingredients (e.g. food additives, dry spices, honey, sugar, sweeteners, etc.), ground coffee, instant coffee and tea leaves.
[00211] In some embodiments, the amount of the compositions of the present disclosure added to beverages or foodstuffs will vary depending on the desired dosage of cannabinoids. For example, in some embodiments each serving, unit or item of foodstuff or beverage will contain between about 0.5 mg and about 100 mg of cannabinoids. In an embodiment, the foodstuff or beverage will contain between about 1.0 mg and about 50 mg of cannabinoids, more particularly between about 1.0 mg and about 25 mg of cannabinoids, between about 2.0 mg and about 20 mg, or between about 2.0 mg and about 10 mg of cannabinoids. In an embodiment, the foodstuff or beverage will contain about 0.5 mg, about 1.0 mg, about 1.5 mg, about 2.0 mg, about 2.5 mg, about 3.0 mg, about 3.5 mg, about 4.0 mg, about 4.5 mg, about 5.0 mg, about 5.5 mg, about 6.0 mg, about 6.5 mg, about 7.0 mg, about 7.5 mg, about 8.0 mg, about 8.5 mg, about 9.0 mg, about 9.5 mg, about 10.0 mg, about 10.5 mg, about 11.0 mg, about 11.5 mg, about 12.0 mg, about 12.5 mg, about 13.0 mg, about 13.5 mg, about 14.0 mg, about 14.5 mg, about 15.0 mg, about
15.5 mg, about 16.0 mg, about 16.5 mg, about 17.0 mg, about 17.5 mg, about 18.0 mg, about 18.5 mg, about 19.0 mg, about 19.5 mg, about 20.0 mg, about 20.5 mg, about 21.0 mg, about 21.5 mg, about 22.0 mg, about 22.5 mg, about 23.0 mg, about 23.5 mg, about 24.0 mg, about 24.5 mg, or about 25.0 mg of cannabinoids.
[00212] In an embodiment, the foodstuff or beverage may contain a cannabinoid concentration of between about 0.01 mg/mL and about 2.5 mg/mL, more particularly between about 0.025 mg/mL and about 1.25 mg/mL, between about 0.025 mg/mL and about 1.0 mg/mL, or between about 0.05 mg/mL and about 0.1 mg/mL. In an embodiment, the foodstuff or beverage may contain a cannabinoid concentration of about 0.01 mg/mL, about 0.02 mg/mL, about 0.03 mg/mL, about 0.04 mg/mL, about 0.05 mg/mL, about 0.06 mg/mL, about 0.07 mg/mL, about 0.08 mg/mL, about 0.09 mg/mL, about 0.1 mg/mL, about 0.2 mg/mL, about 0.3 mg/mL, about 0.4 mg/mL, about 0.5 mg/mL, about 0.6 mg/mL, about 0.7 mg/mL, about 0.8 mg/mL, about 0.9 mg/mL, about 1.0 mg/mL, about 1.25 mg/mL, about
1 .5 mg/mL, about 1.75 mg/mL, about 2.0 mg/mL, about 2.25 mg/mL, or about 2.5 mg/mL. The cannabinoid may be one type of cannabinoid (e.g. CBD or THC) or any combination of cannabinoids. In an embodiment, the cannabinoid is THC. In an embodiment, the cannabinoid is CBD.
[00213] In an embodiment, the product (e.g. beverage or foodstuff) may comprise between about 0.1% and about 25% by weight, particularly about 0.5% and about 25% by weight of the composition as disclosed herein, more particularly between about 1% and about 10% by weight of the composition, and more particularly still between about 1% and about 5% by weight of the composition. In an embodiment, the product may comprise between about 0.5% and about 3% by weight of the composition. In some embodiments, low quantities by weight of the composition may be used due to advantageous properties of the compositions of the present disclosure in stably formulating cannabinoids and/or terpenes.
[00214] In one embodiment, the compositions may be mixed with an aqueous solution to prepare an end use product (e.g. beverage). The aqueous solution can include pure water alone, or an aqueous solution including water and additives such as the additives described above to improve end use product stability, bioavailability, colour, aroma and taste. Particularly, additives may include terpenes, terpenoids, flavonoids, viscosity modifiers, natural emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners (liquid and/or solid), and the like and combinations thereof, as known in the beverage and food arts.
[00215] Beverages may be packaged as individual packages, suitably single use packages, and multiple packages. The packaging can be in air tight containers.
Packaging may be comprised of paper, plastic, metal, and glass. In an embodiment, the packaging may be Tetra Pak™ packaging. Beverages may include bubble containing or producing liquids with dissolved gas or liquids capable of producing gas proximately in time of consumption. In one embodiment of the disclosure, the beverages, optionally comprising additives, modifiers or both, are convenient to consumers, and are manufactured at modest expense. Beverages with dissolved gas may be created by a method comprising addition of carbon dioxide, ozone, oxygen, and nitrogen. For beverages with dissolved gas, dissolved gas may be added to the beverage by methods comprising application of pressure, and adding water with the dissolved gas. The dissolved gas is released from the beverage when pressure is reduced as effervescence. [00216] In another embodiment, the compositions are absorbed into a solid material for use as an end use product. By way of example, the compositions may be absorbed onto one or more of blotter paper, tea leaves, coffee grounds, spices, beverage cap and the like to allow for a convenient beverage, edible or tea bag.
[00217] Advantageously, select embodiments of the products (e.g. beverages and/or foodstuffs) comprising or produced using the water-soluble compositions of the present disclosure are shelf-stable.
[00218] As used in the context of the products herein, "shelf-stable" refers to the composition maintaining its water-soluble nature in an aqueous product at least in respect of the cannabinoid (e.g., no precipitation) for a period of at least 30 days, more suitably, at least 40 days, even more suitably, at least 45 days, and more suitably, at least 50 days, and even more suitably, at least 55 days or longer.
[00219] In any of the embodiments described herein, the product may have a reduced oxygen content, such as by removing the oxygen by means of equipment designed to perform this function or by chemical removal (e.g. N2 purge and/or potassium disulfite). In an embodiment, the oxygen content of the product is between about 0 ppm and about 500 ppm. In an embodiment, the product is sealed until use in order to maintain the reduced oxygen content.
EXAMPLES
[00220] The following examples are included to demonstrate various embodiments of the present disclosure. It should be appreciated by those of skill in the art that the techniques disclosed in the examples that follow represent techniques discovered by the inventors to function well in the practice of the present disclosure, and thus may be considered to constitute preferred modes for its practice. However, those of skill in the art should, in light of the present disclosure, appreciate that many changes can be made in the specific embodiments which are disclosed and still obtain a like or similar result without departing from the scope of the present disclosure.
[00221] Example 1
[00222] Exemplary powder compositions according to the present disclosure, and as described in Table 1 , were prepared generally as follows. [00223] A cannabinoid was dissolved in carrier oil with the application of heat. Separately, an aqueous saccharide solution was prepared and to the solution was added the carrier oil (comprising the cannabinoid) and a surfactant, forming a mixture. The beaker that had contained the cannabinoid and carrier oil was rinsed with small volumes of ethanol, and the ethanol washings were also added to the mixture. The mixture was homogenized and subjected to one or more passes through a microfluidizer (with the exception of the mixtures used to prepare Compositions 3, 4, 6 and 9 which were not passed through a microfluidizer). The mixture was then spray dried with nitrogen and the resulting solid powder was isolated for analysis and characterization.
[00224] Data obtained for percent yield (based on starting weight of 50 g), spray dryer wall content, cannabinoid content (actual vs theoretical), moisture content, and particle size distribution (in water) for the prepared compositions is shown in Table 1 and Figures 1-14.
Table 1 : Characteristics and Analysis of Compositions
Figure imgf000051_0001
*Q-Naturale values reported as weight of solids (1.0 ml of Q-Naturale = 0.21 g)
[00225] Each of the compositions was tested for solubility/dispersibility in either water or a sports drink beverage.
[00226] Compositions 1-7 were tested in water and all displayed solubility and dispersability within 5 minutes with stirring, with the exception of compositions 1 , 2 and 3 which were only partially dispersed after 5 minutes and required slightly more time to become totally dispersed. After being left standing for 30 minutes there was no change and the compositions remained solubilized/dispersed in the water (no precipitate).
[00227] Compositions 8-10 were tested in two different sports drink beverages and all displayed solubility and dispersability within 2 minutes with stirring. Composition 10 displayed foaming after initial stirring, which resolved shortly thereafter. After being left standing for 60 minutes there was no change and the compositions remained solubilized/dispersed in the water (no precipitate).
[00228] Example 2
[00229] An exemplary powder composition according to the present disclosure was prepared according to Example 1. The composition comprised the following components:
Figure imgf000052_0001
[00230] Example 3
[00231] An exemplary powder composition according to the present disclosure was prepared according to Example 1. The composition comprised the following components:
Figure imgf000052_0002
[00232] Example 4
[00233] An exemplary powder composition according to the present disclosure was prepared according to Example 1. The composition comprised the following components:
Figure imgf000052_0003
[00234] Particle size distribution (in water) for the above composition was found to be an average particle size of 107 nm, with a polydispersity of 0.1. [00235] In the present disclosure, all terms referred to in singular form are meant to encompass plural forms of the same. Likewise, all terms referred to in plural form are meant to encompass singular forms of the same. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains.
[00236] As used herein, the term “about” refers to an approximately +/-10 % variation from a given value. It is to be understood that such a variation is always included in any given value provided herein, whether or not it is specifically referred to.
[00237] It should be understood that the compositions and methods are described in terms of "comprising," "containing," or "including" various components or steps, the compositions and methods can also "consist essentially of or "consist of the various components and steps. Moreover, the indefinite articles "a" or "an," as used in the claims, are defined herein to mean one or more than one of the element that it introduces.
[00238] For the sake of brevity, only certain ranges are explicitly disclosed herein. However, ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited. Additionally, whenever a numerical range with a lower limit and an upper limit is disclosed, any number and any included range falling within the range are specifically disclosed. In particular, every range of values (of the form, "from about a to about b," or, equivalently, "from approximately a to b," or, equivalently, "from approximately a-b") disclosed herein is to be understood to set forth every number and range encompassed within the broader range of values even if not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
[00239] Therefore, the present disclosure is well adapted to attain the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the present disclosure may be modified and practiced in different but equivalent manners apparent to those skilled in the art having the benefit of the teachings herein. Although individual embodiments are dis- cussed, the disclosure covers all combinations of all those embodiments. Furthermore, no limitations are intended to the details of construction or design herein shown, other than as described in the claims below. Also, the terms in the claims have their plain, ordinary meaning unless otherwise explicitly and clearly defined by the patentee. It is therefore evident that the particular illustrative embodiments disclosed above may be altered or modified and all such variations are considered within the scope and spirit of the present disclosure. If there is any conflict in the usages of a word or term in this specification and one or more patent(s) or other documents that may be incorporated herein by reference, the definitions that are consistent with this specification should be adopted.
[00240] Many obvious variations of the embodiments set out herein will suggest themselves to those skilled in the art in light of the present disclosure. Such obvious variations are within the full intended scope of the appended claims.

Claims

CLAIMS:
1. A composition comprising: at least one cannabinoid and/or terpene; at least one saccharide; at least one surfactant; and at least one carrier oil.
2. The composition of claim 1 , which is a powder.
3. The composition of claim 1 , wherein the composition further comprises a solvent and is a liquid.
4. The composition of claim 3, wherein the solvent is water and the liquid is an emulsion.
5. The composition of any one of claims 1 to 4, wherein the at least one cannabinoid is A9-THC, A8-THC, trans-A10-THC, cis-A10-THC, THCA, A8-THCA, A9-THCA, THCV, A8-THCV, A9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, CBLVA, cannabicitran, or any combination thereof.
6. The composition of any one of claims 1 to 4, wherein the at least one cannabinoid is
THC, CBD, or a combination thereof.
7. The composition of claim 6, wherein the at least one cannabinoid is THC.
8. The composition of claim 6, wherein the at least one cannabinoid is CBD.
9. The composition of any one of claims 1 to 8, wherein the at least one saccharide is a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or any combination thereof.
53
10. The composition of claim 9, wherein the at least one saccharide is glucose, fructose, galactose, xylose, ribose, inositol, myo-inositol, sucrose, lactose, lactulose, maltose, isomaltose, trehalose, cellobiose, chitobiose, raffinose, stachyose, verbascose, inulin, pectin, amylopectin, beta-glucan, glycogen, maltodextrin or any combination thereof.
11. The composition of claim 9, wherein the at least one saccharide is inulin, pectin, inositol, myo-inositol, or any combination thereof.
12. The composition of claim 9, wherein the at least one saccharide is inulin, inositol, or myo-inositol.
13. The composition of claim 9, wherein the at least one saccharide is myo-inositol or inositol.
14. The composition of any one of claims 1 to 13, wherein the at least one surfactant is a non-ionic surfactant, an anionic surfactant, cationic, an amphoteric surfactant, or a natural surfactant.
15. The composition of claim 14, wherein the non-ionic surfactant is a partial fatty acid ester, a fatty acid ester of glycerol, a fatty alcohol, a sterol, a polyethylene glycol, an ethoxylated fatty acid, an ethoxylated fatty alcohol, an ethoxylated sorbitan ester, an ethoxylated amines or fatty acid amide, a polyglycerol, a polyglyceryl ester, or any combination thereof.
16. The composition of claim 14, wherein the anionic surfactant is sodium stearate, an alkyl sulfate, an alkyl-ether sulfate, a fatty alcohol sulfate, a mono, di- and tri-alkyl phosphoric acid ester or an ethoxylate thereof, a fatty acid lactate ester, a fatty acid citrate ester, a fatty acid citro-glycerin ester, or any combination thereof.
17. The composition of claim 14, wherein the cationic surfactant is a quaternary ammonium compound having a long-chain aliphatic group (e.g. cetrimonium bromide, cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, dimethyldioctadecylammonium chloride, dioctadecyldimethylammonium bromide.
54
18. The composition of claim 14, wherein the amphoteric surfactant is an alkylamininoalkane carboxylic acid, a betaine (e.g. cocamidopropyl betaine), a sulfobetaine, or an imidazoline derivative.
19. The composition of any one of claims 1 to 13, wherein the at least one surfactant comprises a saponin, a lecithin, a gum arabic, or a sterol.
20. The composition of claim 19, wherein the saponin is from Quillaja, Soapwort, Quinoa, Soap nut, Soapweed, Soapbush, Soaproot, Buffaloberry, or any combination thereof
21. The composition of claim 19, wherein the at least one surfactant comprises Quillaja saponins.
22. The composition of claim 21 , wherein the surfactant comprising Quillaja saponins is a Q-NATURALE® surfactant, Saponin from Quillaja Bark, Saponin Quillaja sp., a Quillaja extract, purified Quillaja saponins, or any combination thereof.
23. The composition of any one of claims 1 to 13, wherein the at least one surfactant is a Q-NATURALE® surfactant.
24. The composition of claim 19, wherein the lecithin is a natural lecithin from soybean, canola, eggs, milk, marine sources, rapeseed, cottonseed, sunflower seed, or any combination thereof.
25. The composition of claim 19, wherein the surfactant comprising Lecithin is Lipoid S 40, Lipoid H 50, Lipoid PHOSAL® 50 SA, Lipoid PHOSAL® 53 MCT, Lipoid P 75, Lipoid S 75, Lipoid S 80, Lipoid E 80, PHOSPHOLIPON® 85 G, Lipoid PHOSPHOLIPON® 90 G, Lipoid PHOSPHOLIPON® 90 H, Lipoid H 100, or any combination thereof.
26. The composition of any one of claims 1 to 13, wherein the at least one surfactant is Tween 20, Tween 40, Tween 45, Tween 60, Tween 65, Tween 80, Tween 81 , Tween 85, Span 20, Span 40, Span 60, Span 80, Span 83, Span 85, Span 120, or any combination thereof.
55
27. The composition of any one of claims 1 to 13, wherein the at least one surfactant is Polyglyceryl 4 Caprate, Polyglyceryl-4 Caprylate, Polyglyceryl-4 Isostearate, Polyglyceryl-4 Laurate, Polyglyceryl-4, Oleate, Polyglyceryl-5 Dioleate, Polyglyceryl-5 Isostearate, Polyglyceryl-5 Laurate, Polyglyceryl-5 Myristate, Polyglyceryl-5 Oleate, Polyglyceryl-5 Stearate, Polyglyceryl-5 Triisostearate, Polyglyceryl-5 Trioleate, Polyglyceryl-6 Dioleate, Polyglyceryl-6 Distearate, Polyglyceryl-6 Isostearate, Polyglyceryl-6 Octastearate, Polyglyceryl-6 Oleate, Polyglyceryl-6 Pentastearate, Polyglyceryl-6 Stearate, Polyglyceryl-6 Tricaprylate, Polyglyceryl-8 Decaerucate/Decaisostearate/Decaricinoleate, Polyglyceryl-8 Oleate, Polyglyceryl-8 Stearate, Polyglyceryl-10 Behenate/Eicosadioate, Polyglyceryl-10 Caprylate/Caprate, Polyglyceryl-10 Deca isostea rate, Polyglyceryl-10 Decaoleate, Polyglyceryl-10 Diisostearate, Polyglyceryl-10 Dioleate, Polyglyceryl-10 Dipalmitate, Polyglyceryl-10 Distearate, Polyglyceryl-10 Heptahydroxystearate, Polyglyceryl-10 Hydroxystearate/Stearate/Eicosadioate and Polyglyceryl-10 Fatty Ester (POLYALDO® 10 2-P), Polyglyceryl-10 Isostearate, Polyglyceryl-10 Laurate, Polyglyceryl-10 Linoleate, Polyglyceryl-10 Myristate, Polyglyceryl-10 Nonaisostearate, Polyglyceryl-10 Oleate, Polyglyceryl-10 Palmitate, Polyglyceryl-10 Pentahydroxystearate, Polyglyceryl-10 Pentaisostearate, Polyglyceryl-10 Pentaoleate, Polyglyceryl-10 Pentastearate, Polyglyceryl 10 Stearate, Polyglyceryl-10 Tristearate, or any combination thereof.
28. The composition of any one of claims 1 to 13, wherein the at least one surfactant comprises almond oil PEG-6 esters, almond oil PEG-60 esters, apricot kernel oil PEG-6 esters, caprylic/capric triglycerides PEG-4 esters, caprylic/capric glycerides PEG-6 esters, caprylic/capric glycerides PEG-8 esters, castor oil PEG-50 esters, hydrogenated castor oil PEG-5 esters, hydrogenated castor oil PEG-7 esters, hydrogenated castor oil PEG-9 esters, corn oil PEG-6 esters, corn oil PEG-8 esters, corn glycerides PEG-60 esters, olive oil PEG-6 esters, hydrogenated palm/palm kernel oil PEG-6 esters, hydrogenated palm/ palm kernel oil PEG-6 esters with palm kernel oil and PEG-6 and palm oil, palm kernel oil PEG-40 esters, peanut oil PEG-6 esters, glycerol esters of saturated C8-C18 fatty acids, glyceryl esters of saturated C 12-CI 8 fatty acids, glyceryl laurate/PEG-32 laurate, glyceryl laurate glyceryl/PEG 20 laurate, glyceryl laurate glyceryl/PEG 32 laurate, glyceryl, laurate glyceryl/PEG 40 laurate, glyceryl oleate/PEG-20 glyceryl, glyceryl oleate/PEG-30 oleate, glyceryl palmitostearate/PEG-32 palmitostearate, glyceryl stearate/PEG stearate, glyceryl stearate/PEG-32 stearate, saturated polyglycolized glycerides, triisostearin PEG-6 esters, triolein PEG-6 esters, trioleate PEG-25 esters, polyoxyl 35 castor oil, polyoxyl 40
56 hydrogenated castor oil, polyoxyl 60 hydrogenated castor oil, PEG-8 caproate, PEG-8 caprylate, PEG-8 caprate PEG-8 laurate, PEG-8 oleate, PEG- 8 stearate, PEG-9 caproate, PEG-9 caprylate, PEG-9 caprate PEG-9 laurate, PEG-9 oleate, PEG- 9 stearate, PEG-10 caproate, PEG-10 caprylate, PEG-10 caprate PEG-10 laurate, PEG-10 oleate, PEG-10 stearate, PEG-10 laurate, PEG- 12 oleate, PEG- 15 oleate, PEG-20 laurate, PEG-20 oleate, caprylate/caprate diglycerides, glyceryl monooleate, glyceryl ricinoleate, glyceryl laurate, glyceryl dilaurate, glyceryl dioleate, glyceryl mono/dioleate, glyceryl caprylate/caprate, medium chain (C8/C10) mono- and diglycerides, mono-and diacetylated monoglycerides, polyglyceryl oleate, polyglyceryl-2 dioleate, poly glyceryl- 10 trioleate, poly glyceryl- 10 laurate, polyglyceryl-10 oleate, polyglyceryl- 10 mono dioleate, propylene glycol caprylate/caprate, propylene glycol dicaprylate/ dicaprate, propylene glycol monolaurate, propylene glycol ricinoleate, propylene glycol monooleate, propylene glycol dicaprylate/dicaprate, propylene glycol dioctanoate, PEG-20 sorbitan monolaurate, PEG-20 sorbitan monopalmitate, PEG-20 sorbitan monostearate, PEG-20 sorbitan monooleate, poloxamers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monoleate, sorbitan monostearate, sorbitan tristearate, d-a-tocopheryl polyethylene glycol 1000 succinate, polysorbate 20, polysorbate, polyethyleneglycol 660 12-hydroxystearate, or any combination thereof.
29. The composition of any one of claims 1 to 13, wherein the at least one surfactant is Polyoxyethylene (10) cetyl ether (Ceteth-10), Polyoxyethylene (20) cetyl ether (Ceteth-20), Polyoxyethylene (20) Cetyl Stearyl Ether (Ceteareth-20), Alkoxylated ether (lsoceteth-20); Alkoxylated ether and Aqua (lsocetech-20), Ethoxylated Fatty Alcohol (Laureth-4), Polyoxyethylene (23) lauryl ether (Laureth-23), Polyoxyethylene (23) lauryl ether and Aqua (Laureth-23), Polyoxyethylene (10) oleyl ether (Oleth-10), Polyoxyethylene (20) oleyl ether (Oleth-20), Polyoxyethylene (10) stearyl ether (Steareth-10), Polyoxyethylene (20) stearyl ether (Steareth-20), Polyoxyethylene (100) stearyl ether (Steareth-100), ethoxylated fatty alcohols (Steareth-21), or any combination thereof.
30. The composition of any one of claims 1 to 29, wherein the at least one carrier oil is a medium-chain triglyceride (MCT), a long-chain triglyceride (LOT), glycerine/glycerol, a monoglyceride, or any combination thereof.
31. The composition of any one of claims 1 to 29, wherein the at least one carrier oil is glyceryl monostearate, glyceryl hydroxystearate, glyceryl monoleate, winterized glyceryl monoleate, monolaurin, glyceryl monolinoleate, Maisine® CC, Peceol™, Labrasol, Labrafac Lipophile WL 1349, Labrafil M1944, Plural Oliqiue CC 497, Transcutol HP, Gelucire 48/16, Vitamin E TPGS, or any combination thereof.
32. The composition of any one of claims 1 to 29, wherein the at least one carrier oil is a coconut oil, corn oil, canola oil, olive oil, avocado oil, vegetable oil, flaxseed oil, palm oil, palm kernel oil, peanut oil, sunflower oil, rice bran oil, safflower oil, jojoba oil, argan oil, grapeseed oil, castor oil, wheat germ oil, peppermint oil, hemp oil, sesame oil, or any combination thereof.
33. The composition of any one of claims 1 to 32, which comprises between about 0.1% and about 25% by weight of the at least one cannabinoid; between about 25% and about 85% by weight of the at least one saccharide, between about 0.5% and about 15% of the at least one surfactant; and between about 0.5% and 25% of the at least one carrier oil.
34. The composition of any one of claims 1 to 33, which comprises a ratio of saccharide:surfactant of between about 40:1 and 1 :2.
35. The composition of any one of claims 1 to 34, which comprises a ratio of saccharide:carrier oil of between about 15:1 and 1 :1.
36. The composition of any one of claims 1 to 35, which comprises a ratio of carrier oiksurfactant of between about 15:1 and 1 :5.
37. A beverage comprising the composition of any one of claims 1 to 36.
38. The beverage of claim 37, which comprises one or more salts.
39. The beverage of claim 37 or 38, which is a sports drink beverage.
40. A foodstuff comprising the composition of any one of claims 1 to 36.
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WO2024047529A1 (en) * 2022-08-30 2024-03-07 2682130 Ontario Limited Water-dispersible cannabinoid emulsion formulations, methods of making and applications

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WO2023129818A1 (en) * 2021-12-29 2023-07-06 Pegasus Laboratories, Inc. Granular composition providing water dispersible cannabinoids and methods of making the same
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