WO2022140849A1 - Cannabinoid compositions with taste-barrier properties - Google Patents

Cannabinoid compositions with taste-barrier properties Download PDF

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Publication number
WO2022140849A1
WO2022140849A1 PCT/CA2021/051888 CA2021051888W WO2022140849A1 WO 2022140849 A1 WO2022140849 A1 WO 2022140849A1 CA 2021051888 W CA2021051888 W CA 2021051888W WO 2022140849 A1 WO2022140849 A1 WO 2022140849A1
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WIPO (PCT)
Prior art keywords
cannabinoid
carrier
cannabis
infused
cannabinoid composition
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PCT/CA2021/051888
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French (fr)
Inventor
Justin CONWAY
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Hexo Operations Inc.
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Publication of WO2022140849A1 publication Critical patent/WO2022140849A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
    • A23P10/47—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added using additives, e.g. emulsifiers, wetting agents or dust-binding agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • 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

Definitions

  • the present specification relates to cannabinoid compositions having taste-barrier properties, methods of making and using same. Cannabis-infused products containing such cannabinoid compositions are also encompassed by the present disclosure.
  • Cannabis-infused products are expected to grow in popularity due to the existing and/or expected legalization of these products in Canada and other countries (e.g., United States). As a result, attention has turned to how to prepare industrial scale quantities of these products to meet consumer demands.
  • the cannabinoid component comprises the cannabinoid and a carrier oil.
  • the carrier in particulate form includes silicon dioxide.
  • the food grade polymer comprises pectin, gums, chitosan or pullulan.
  • the emulsion is a microemulsion.
  • the cannabis-infused product is a solid or semi-solid edible cannabis-infused product.
  • the cannabis-infused product is a liquid cannabis-infused product.
  • the cannabis infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles.
  • the present disclosure relates to a solid or semisolid edible cannabis-infused product comprising the cannabinoid composition described herein.
  • the present disclosure relates to a method for preparing a cannabinoid composition.
  • the method comprises: a) providing an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid; and b) loading the emulsion in a carrier in particulate form, the carrier comprising a mesoporous internal network, wherein the cannabinoid composition is in the form of a powder.
  • the method may have one or more of the following features:
  • the loading comprises encapsulating the emulsion in the carrier in particulate form.
  • the loading comprises plating the emulsion in the carrier in particulate form.
  • the method further comprises dehydrating the powder.
  • the method further comprises coating at least a portion of a surface of powder particles with a coating.
  • the coating includes a food grade polymer.
  • the food grade polymer comprises pectin, gums, chitosan or pullulan.
  • the method further comprises mixing the powder with a product base.
  • the method further comprises dehydrating the powder mixed with the product base.
  • the product base is for manufacturing a solid or semi-solid edible cannabis- infused product.
  • the solid or semi-solid edible cannabis-infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles.
  • the liquid cannabis-infused product is a cannabis-infused beverage, a cannabis- infused drop, a cannabis-infused tincture and a cannabis-infused spray.
  • the cannabinoid component comprises the cannabinoid in combination with a carrier oil.
  • the carrier oil comprises medium-chain triglycerides (MCT), long chain triglycerides (LCT), or a combination thereof.
  • the cannabinoid component comprises cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
  • CBD cannabidiol
  • THC tetrahydrocannabinol
  • the carrier is an inert carrier.
  • the inert carrier is water soluble or water insoluble.
  • the carrier includes modified starch.
  • the carrier includes tricalcium phosphate.
  • the carrier has pores having a diameter of between about 2 nm and about 1 pm according to IIIPAC nomenclature.
  • the emulsion is a microemulsion.
  • the emulsion is a nanoemulsion.
  • the present inventors have developed cannabinoid compositions that have reduced bitter-tasting characteristics, and that can be suitable for making cannabis-infused products.
  • the herein described cannabinoid compositions effectively masks the bitter and off-taste of cannabis-infused products while avoiding having to add such taste masking ingredients or flavors.
  • composition of the present disclosure also releases a nanoemulsion upon contacting an aqueous medium, in the case where the composition includes a carrier loaded with an emulsion (e.g., whether the emulsion loaded is a nanoemulsion or microemulsion).
  • the present disclosure relates to cannabinoid compositions for making a cannabis-infused product.
  • cannabinoid compositions for making a cannabis-infused product.
  • use of the herein described cannabinoid compositions when making cannabis-infused products effectively masks the bitter and off-taste while avoiding having to add such taste masking ingredients or flavors.
  • the cannabinoid composition of the present disclosure comprises an emulsion and a carrier in particulate form, where the emulsion is loaded into the carrier, and the cannabinoid composition has the appearance of a powder.
  • loading the emulsion in the solid carrier described herein offers several technical advantages. For example, as the emulsion is loaded within the internal porous network of the carrier, it is believed that this creates a physical barrier between the emulsion containing the cannabinoid component and the aqueous environment in the user’s mouth (saliva). Such physical barrier thus minimizes exposure of the emulsion to the user’s taste buds. For example, when the cannabinoid composition is incorporated into an edible cannabis-infused product, the cannabinoid composition is effectively locked into the cannabis-infused product food matrix while a consumer is masticating.
  • the solid matrix of the edible product substantially “protects” the emulsion at the time the edible product is consumed by the user (e.g., chewed) from being significantly released from the carrier, such that the edible product is not associated with a bitter or off-taste. It is only as the matrix of the edible is more fully broken down in the gastrointestinal tract that the emulsion is effectively released from the carrier in the form of a nanoemulsion. Also, as the emulsion released is a nanoemulsion, the herein described cannabis- infused product affords the desired fast onset of the cannabinoid. This confers “taste masking” properties to the cannabinoid composition and thus the user perceives less bitterness and/or off- taste when consuming the cannabis-infused product. Other possible benefits include oxidation protection and compatibility with oil and aqueous loads.
  • the resulting cannabinoid composition can thus be used as an ingredient for manufacturing cannabis-infused products or any other application requiring a solid form of cannabinoids. Further, this also allows obtaining a fast cannabinoid effect onset in a wider variety of cannabis-infused products with acceptable taste.
  • the cannabinoid compositions of the present disclosure include a “cannabinoid component” that includes a cannabinoid.
  • Cannabinoids may also have application as neuroprotectants, for example, in limiting neurological damage following ischemic insults, such as stroke and trauma, or in the treatment of neurodegenerative diseases such as Alzheimer’s disease, Parkinson’s disease and HIV dementia.
  • Cannabinoids for inclusion in the compositions of the present disclosure include phytocannabinoids (i.e., found in cannabis and some other plants) and synthetic cannabinoids (i.e., manufactured artificially).
  • Cannabinoids may be obtained from any suitable source material including, but not limited to, cannabis or hemp plant material (e.g., flowers, seeds, trichomes, and kief from cannabis plants) or manufactured (for example cannabinoids produced in yeast, for example as described in WO WO2018/148848).
  • cannabis or hemp plant material e.g., flowers, seeds, trichomes, and kief from cannabis plants
  • cannabinoids produced in yeast for example as described in WO WO2018/148848
  • the term “cannabis plant(s)” encompasses wild type Cannabis (including but not limited to the species Cannabis sativa, Cannabis indica and Cannabis ruderalis) and also variants thereof, including cannabis chemovars (or “strains”) that naturally contain different amounts of the individual cannabinoids.
  • the distillate may be further cut with one or more terpenes.
  • the distillate may be further purified, for example using chromatographic and other separation methods known in the art, to obtain an “isolate.”
  • pure or isolated cannabinoids such as those provided in a cannabis extract, may be combined with water, lipids, hydrocarbons, ethanol or mixtures thereof.
  • the cannabinoid may be an isolated cannabinoid, such as a cannabis extract, having >75% purity (as in the case of a crude extract), or > 80% purity (as in the case of a distillate), or >95% purity (as in the case of an isolate).
  • the cannabinoid may have a purity such as > 75%, or > 80%, or > 90%, or > 95%, or > 98%, or > 98%, or > 99%, or > 99.5%.
  • Examples of synthetic cannabinoids include, but are not limited to, naphthoylindoles, naphthylmethylindoles, naphthoylpyrroles, naphthylmethylindenes, phenylacetylindoles, cyclohexylphenols, tetramethylcyclopropylindoles, adamantoylindoles, indazole carboxamides, quinolinyl esters, and combinations thereof.
  • Cannabidiol means one or more of the following compounds: A 5 -cannabidiol (2- (6-isopropenyl-3-methyl-5-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 4 -cannabidiol (2-(6- isopropenyl-3-methyl-4-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 3 -cannabidiol (2-(6- isopropenyl-3-methyl-3-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 3J -cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-l-yl)-5-pentyl-l,3-benzenediol); A 2 -cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-
  • the cannabinoid component may include a single cannabinoid or may include a combination of two or more cannabinoids.
  • the cannabinoid component includes cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
  • the cannabinoid component includes a mixture of THC and CBD.
  • the w/w ratio of THC to CBD in the cannabinoid component may be between about 1:1000 and about 1000:1.
  • the (w/w) ratio of THC to CBD in the component may be about 1:1000, about 1 :900, about 1 :800, about 1 :700, about 1 :600, about 1 :500, about 1 :400, about 1 :300, about 1:250, about 1:200, about 1:150, about 1:100, about 1:90, about 1:80, about 1:70, about 1:60, about 1:50, about 1:45, about 1:40, about 1:35, about 1:30, about 1:29, about 1:28, about 1:27, about 1:26, about 1:25, about 1:24, about 1:23, about 1:22, about 1:21, about 1:20, about 1:19, about 1:18, about 1:17, about 1:16, about 1:15, about 1:14, about 1:13, about 1:12, about 1:11, about 1:10, about 1
  • Non-limiting examples of carrier oils include: borage oil, coconut oil, cottonseed oil, soybean oil, safflower oil, sunflower oil, corn oil, olive oil, palm oil, peanut oil, almond oil, sesame oil, rapeseed oil, peppermint oil, poppy seed oil, canola oil, palm kernel oil, hydrogenated soybean oil, hydrogenated vegetable oils, glyceryl esters of saturated fatty acids, glyceryl behenate, glyceryl distearate, glyceryl isostearate, glyceryl laurate, glyceryl monooleate (e.g., PeceolTM), glyceryl, monolinoleate, glyceryl palmitate, glyceryl palmitostearate, glyceryl ricinoleate, glyceryl stearate, polyglyceryl 10-oleate, polyglyceryl 3-oleate, polyglyceryl 4-oleate, polyglyceryl 10-tetral
  • Terpenes refers to refer to a class of chemical components comprised of the fundamental building block of isoprene, which can be linked to form linear structures or rings. Terpenes may include hemiterpenes (single isoprenoid unit), monoterpenes (two units), sesquiterpenes (three units), diterpenes (four units), sesterterpenes (five units), triterpenes (six units), and so on. At least some terpenes are expected to interact with, and potentiate the activity of, cannabinoids.
  • nanoemulsion refers to a kinetically stabilized emulsion with nanometer to micrometer sized particles. Nanoemulsions typically comprise an oil phase, a water phase, and an emulsifier - though additional components may be included. Generally, a high energy input is required to break the emulsion particles into the desired size, however selfemulsifying nanoemulsions are known in the art. Generally, nanoemulsions are known in the art, and several patent and non-patent literature is available to the person of skill.
  • microemulsions cannot be characterized by a PSD and/or PDI, as further described below, as there are no droplet particles that are formed initially. It is only when a microemulsion is contacted with an aqueous medium that it spontaneous generates oil droplets in the nanometer size range.
  • any microemulsion formulations known in the art and suitable for incorporation of a cannabinoid component can be used in the compositions as described herein.
  • microemulsions and nanoemulsions likely resulting from the prefixes “micro” and “nano”. Applying known nomenclature to the context of an emulsion, and without wishing to be bound by theory, these two prefixes would give the impression to reference a specific emulsion particle size range. However, in the context of emulsions and as used herein, the difference between microemulsions and nanoemulsions is more fundamental and structural, and is unrelated to the particle size of an emulsion.
  • PSD of an emulsion When PSD of an emulsion is measured, it is expressed as a distribution of particle sizes.
  • the polydispersity index (PDI) is a reflection of how monodisperse a population with a given PSD is; a lower PDI means that the majority of particles have the same PSD, while a higher PDI means that particles have a wide range of PSD possibly indicating a multimodal particle size distribution.
  • the term “polydispersity index” or “PDI” refers to a number calculated from a simple 2 parameter fit to the correlation data (the cumulants analysis).
  • the PDI is dimensionless and scaled such that values smaller than 0.05 are seen with highly monodisperse standards. Values greater than 0.7 indicate that the sample has a very broad size distribution.
  • the various size distribution algorithms work with data that fall between these two extremes. The calculations for these parameters are defined in the ISO standard document 13321 :1996 E and ISO 22412:2008.
  • the nanoemulsion (i.e. , as loaded in the carrier and/or released from the microemulsion) has a PSD of between about 1 nm and about 999 nm (where the size is the hydrodynamic diameter), including any amount therebetween or any ranges therein.
  • the PSD can be of between about 5 nm and about 500 nm, including any amount therebetween or any ranges therein, in some cases between about 10 nm and about 250 nm, including any amount therebetween or any ranges therein, in some cases between about 25 nm and about 125 nm, including any amount therebetween or any ranges therein.
  • the nanoemulsion can be made of at least 95%, or at least 96%, or at least 97%, or at least 98%, or at least 99% of particles in the nanometric range (i.e. , from 1 to 999 nm).
  • the emulsion is a microemulsion and includes minimal amounts of water.
  • microemulsions may typically include about 10 wt.% of water therein, sometimes even less.
  • Microemulsions are predominantly oil based (including surfactants), as such they will not solubilize water soluble carriers. This renders them compatible with both soluble and insoluble carriers. Depending on the carrier they can be loaded via capillary diffusion or through plating/agglomeration methods.
  • the water-insoluble carrier can be an insoluble pharmaceutical carrier, where the chemical composition of the carrier comprises cyclodextrin, tricalcium phosphate, carboxymethylcellulose sodium, sodium starch gluconate, croscarmellose sodium, silicon dioxide and the likes, as further described below.
  • the carrier is spray-dried tricalcium phosphate TRI-CAFOS® from Chemische Fabrik Budenheim KG, Tabulose® from Roquette Freres SA, Explosol® from Roquette Freres SA, Solutab® from Roquette Freres SA or FujisilTM from Fuji Chemical Industries USA, Inc.
  • the carrier is amorphous silica, such as but not limited to silicon dioxide.
  • the silicon dioxide is spray-dried granular silicon dioxide FujisilTM from Fuji Chemical Industries USA, Inc., Omyapharm® from Omya International AG or Floguard from PPG Industries. Inc.
  • the carrier is a modified starch or starch derivative.
  • modified starch refers to a native starch that has been subjected to a physical, enzymatic and/or chemical treatment to alter at least one of its physicochemical properties.
  • the carrier can be characterized by a PSD.
  • the carrier in particulate form has a PSD of between about 1 pm and about 750 pm, including any amount therebetween or any ranges therein, in some cases between about 1 pm and about 500 pm, including any amount therebetween or any ranges therein, about 10 pm and about 250 pm, including any amount therebetween or any ranges therein.
  • the carrier has a specific surface area of between about 25 m 2 /g and about 1000 m 2 /g, including any amount therebetween or any ranges therein, in some cases between about 100 m 2 /g and about 750 m 2 /g, including any amount therebetween or any ranges therein, in some cases between about 200 m 2 /g and about 500 m 2 /g, including any amount therebetween or any ranges therein.
  • the cannabis-infused product is a solid or semi-solid edible product.
  • Edible products come in many forms and can be any product that is suitable, e.g., nontoxic, for placing into the mouth of a human or animal, whether ingested, absorbed, or only chewed or sucked on and at least a portion discarded, etc.
  • Illustrative examples of human edible products include but are not limited to confections such as chewing or bubble gums, mints, suckers, jawbreakers, lozenges, hard candies, gummy candies, taffies, and chocolates; baked goods such as muffins, brownies, cookies, crackers, and granola bars, and meal replacement bars; and dissolving strips.
  • a chewing-gum may have a hard shell (akin an ExcelTM chewing-gum) or not (akin Juicy FruitTM).
  • cannabis-infused products may include gels, creams, custard, pudding, honey, syrup, broth, soup, gelatin, yogurt, puree, jelly, sauce, liquid eggs, or salad dressing.
  • a beverage includes, but without being limited to, drinking water, milk (both diary and non-diary), juice, a smoothie, coffee or a caffeinated beverage, tea, herbal tea, a cocoa beverage, a carbonated drink, a nitrogenated drink, an energy drink, a drinkable yogurt, a fermented beverage, or an alcoholic or non-alcoholic drink.
  • An alcoholic or non-alcoholic drink includes but is not limited to, alcoholic or non-alcoholic beer, lager, cider, spirits, wine/fortified wine, and cocktails.
  • a cannabis-infused muffin in order to obtain a cannabis-infused muffin, one may proceed to mix the muffin ingredients (e.g., flour, sugar, milk, etc.) with the herein described cannabinoid composition and process (bake) the mixture to obtain the cannabis-infused muffin.
  • the person of skill may proceed to add the herein described cannabinoid composition on top of the finished product (e.g., a muffin or a potato chip) thus sprinkling the cannabinoid composition onto the finished product.
  • Cannabis-infused products are typically used for recreational and/or medicinal uses.
  • cannabis-infused products can be used to achieve a desired effect in a user, such as a psychoactive effect, a physiological effect, or a treatment of a condition.
  • a psychoactive effect it is meant a substantial effect on mood, perception, consciousness, cognition, or behavior of a subject resulting from changes in the normal functioning of the nervous system.
  • physiological effect it is meant an effect associated with a feeling of physical and/or emotional satisfaction.
  • treatment of a condition it is meant the treatment or alleviation of a disease or condition by absorption of cannabinoid(s) at sufficient amounts to mediate the therapeutic effects.
  • the oil phase THC distillate and MCT carrier oil were mixed in a beaker at 80°C with medium agitation for 10 minutes. TocobiolTM and glycerol were slowly added to the mixture, with medium agitation and heat for approximately 20 minutes.
  • the taste index is categorised as a scale of 0 - 10 to indicate bitterness (0- No bitter taste: Taste of white chocolate, and taste index increases with increase in bitterness from 1 to 10).
  • Table 11C The codes of different nanoemulsion formulations and their description is set forth in Table 11C:

Abstract

The present disclosure relates to cannabinoid compositions that have reduced bitter-tasting characteristics, which are suitable for making cannabis-infused products. The cannabinoid compositions effectively mask the bitter and off-taste of cannabis-infused products while avoiding having to use taste masking ingredients or flavors. The cannabinoid composition is in the form of a powder and comprises a) an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid, and b) a carrier in particulate form comprising a mesoporous internal network, wherein the emulsion is loaded in particles of the carrier, and wherein upon contacting the cannabinoid composition with an aqueous medium, the cannabinoid composition releases a nanoemulsion. The disclosure also relates to methods of manufacture and using same.

Description

CANNABINOID COMPOSITIONS WITH TASTE-BARRIER PROPERTIES
CROSS-REFERENCE TO RELATED APPLICATION
[0001] The present application claims the benefit of U.S. provisional patent application serial number 63/133,674 filed on January 4, 2021. The contents of the above-referenced document are incorporated herein by reference in their entirety.
TECHNICAL FIELD
[0002] The present specification relates to cannabinoid compositions having taste-barrier properties, methods of making and using same. Cannabis-infused products containing such cannabinoid compositions are also encompassed by the present disclosure.
BACKGROUND
[0003] Cannabis-infused products are expected to grow in popularity due to the existing and/or expected legalization of these products in Canada and other countries (e.g., United States). As a result, attention has turned to how to prepare industrial scale quantities of these products to meet consumer demands.
[0004] Manufacturing cannabis-infused products presents unique challenges. For example, cannabis-infused products often have a bitter aftertaste imparted by the cannabis extracts used to make the cannabis-infused products. This is particularly true when cannabis extracts such as full-spectrum extracts or distillates, which may have a noticeable bitter aftertaste, are used as infusing ingredient. This unpleasant gustatory experience is further exacerbated when making aqueous-based cannabis-infused products because this requires emulsifying the cannabis extracts - i.e., emulsifiers often also have a bitter taste. To further add to the complexity of developing cannabis-infused products, consumers demand faster onset which in turn requires emulsifying the cannabis extracts to obtain emulsions with smaller particle size, preferably in the nanosize scale. Such small particle sizes, however, effectively increase the particles’ surface area, which exacerbates the off-flavours as the increased particle size of the emulsion particles is now fully exposed to and interacts with taste receptors.
[0005] Thus, there remains a need for improved cannabinoid compositions for making cannabis- infused products. SUMMARY
[0006] This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key aspects or essential aspects of the claimed subject matter.
[0007] In accordance with one broad aspect, the present disclosure relates to a cannabinoid composition for manufacturing a cannabis-infused product. The cannabinoid composition is in the form of a powder and comprises a) an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid, and b) a carrier in particulate form comprising a mesoporous internal network, wherein the emulsion is loaded in particles of the carrier. Upon contacting the cannabinoid composition with an aqueous medium, the cannabinoid composition releases a nanoemulsion.
[0008] In some implementations, the cannabinoid composition may have one or more of the following features:
• the cannabinoid component comprises the cannabinoid and a carrier oil.
• the carrier oil comprises medium-chain triglycerides (MCT), long chain triglycerides (LCT), or a combination thereof.
• the cannabinoid comprises cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
• the carrier in particulate form is an inert carrier and can be water soluble or water insoluble.
• the carrier in particulate form includes a modified starch.
• the modified starch is N-Zorbit 2144.
• the carrier in particulate form includes tricalcium phosphate.
• the carrier in particulate form includes silicon dioxide.
• the carrier has pores having a diameter of between about 2 nm and about 1 pm according to IUPAC nomenclature. the particles of the carrier further comprise a coating on at least a portion of a surface thereof.
• the coating includes a food grade polymer.
• the food grade polymer comprises pectin, gums, chitosan or pullulan.
• the emulsion is a microemulsion.
• the emulsion is a nanoemulsion.
• the cannabis-infused product is a solid or semi-solid edible cannabis-infused product.
• the cannabis-infused product is a liquid cannabis-infused product.
• the cannabis-infused product is a cannabis-infused beverage, a cannabis-infused tincture, or a cannabis-infused spray.
• The cannabis infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles.
[0009] In accordance with one broad aspect, the present disclosure relates to a solid or semisolid edible cannabis-infused product comprising the cannabinoid composition described herein.
[0010] In accordance with one broad aspect, the present disclosure relates to a liquid cannabis- infused product comprising the cannabinoid composition described herein.
[0011] In accordance with one broad aspect, the present disclosure relates to a method for preparing a cannabinoid composition. The method comprises: a) providing an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid; and b) loading the emulsion in a carrier in particulate form, the carrier comprising a mesoporous internal network, wherein the cannabinoid composition is in the form of a powder.
[0012] In some implementations, the method may have one or more of the following features:
• the loading comprises encapsulating the emulsion in the carrier in particulate form. the loading comprises plating the emulsion in the carrier in particulate form. the method further comprises dehydrating the powder.
• the method further comprises coating at least a portion of a surface of powder particles with a coating.
• the coating includes a food grade polymer.
• the food grade polymer comprises pectin, gums, chitosan or pullulan.
• the method further comprises mixing the powder with a product base.
• the method further comprises dehydrating the powder mixed with the product base.
• the product base is for manufacturing a solid or semi-solid edible cannabis- infused product.
• the solid or semi-solid edible cannabis-infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles.
• the product base is for manufacturing a liquid cannabis-infused product.
• the liquid cannabis-infused product is a cannabis-infused beverage, a cannabis- infused drop, a cannabis-infused tincture and a cannabis-infused spray.
• the cannabinoid composition has taste-masking properties.
• the cannabinoid component comprises the cannabinoid in combination with a carrier oil.
• the carrier oil comprises medium-chain triglycerides (MCT), long chain triglycerides (LCT), or a combination thereof.
• the cannabinoid component comprises cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
• the carrier is an inert carrier. the inert carrier is water soluble or water insoluble. the carrier includes modified starch.
• the modified starch is N-Zorbit 2144.
• the carrier includes tricalcium phosphate.
• the carrier includes silicon dioxide.
• the carrier has pores having a diameter of between about 2 nm and about 1 pm according to IIIPAC nomenclature.
• the emulsion is a microemulsion.
• the emulsion is a nanoemulsion.
[0013] All features of exemplary embodiments which are described in this disclosure and are not mutually exclusive can be combined with one another. Elements of one embodiment can be utilized in the other embodiments without further mention. Other aspects and features of the present invention will become apparent to those ordinarily skilled in the art upon review of the following description of specific embodiments.
DETAILED DESCRIPTION
[0014] A detailed description of one or more embodiments of the invention is provided below. The invention is described in connection with such embodiments, but the invention is not limited to any embodiment. The scope of the invention is limited only by the claims. Numerous specific details are set forth in the following description to provide a thorough understanding of the invention. These details are provided for the purpose of non-limiting examples and the invention may be practiced according to the claims without some or all these specific details. For the sake of clarity, technical material that is known in the technical fields related to the invention has not been described in detail so that the invention is not unnecessarily obscured.
[0015] The present inventors have developed cannabinoid compositions that have reduced bitter-tasting characteristics, and that can be suitable for making cannabis-infused products. In contrast to common approaches that aim to mask bitter and off-taste in cannabis-infused product with the addition of masking ingredients or flavors (e.g., sugars), the herein described cannabinoid compositions effectively masks the bitter and off-taste of cannabis-infused products while avoiding having to add such taste masking ingredients or flavors.
[0016] Surprisingly and unexpectedly, it was also observed that the composition of the present disclosure also releases a nanoemulsion upon contacting an aqueous medium, in the case where the composition includes a carrier loaded with an emulsion (e.g., whether the emulsion loaded is a nanoemulsion or microemulsion).
[0017] These and other advantages of the herein described composition will become apparent to the person of skill based on the teachings described herein.
Composition
[0018] In one broad aspect, the present disclosure relates to cannabinoid compositions for making a cannabis-infused product. In contrast to common approaches that aim to mask bitter and off-taste in cannabis-infused product with the addition therein of masking ingredients or flavors (e.g., sugars), use of the herein described cannabinoid compositions when making cannabis-infused products effectively masks the bitter and off-taste while avoiding having to add such taste masking ingredients or flavors.
[0019] The cannabinoid composition of the present disclosure comprises an emulsion and a carrier in particulate form, where the emulsion is loaded into the carrier, and the cannabinoid composition has the appearance of a powder.
[0020] In some embodiments, the cannabinoid composition can be used by its manufacturer to obtain the cannabis-infused product, ready for packaging and commercialization. In some embodiments, the cannabinoid composition may be packaged and sold to a product manufacturer, which can then use same to obtain the cannabis-infused product. In some embodiments, the cannabinoid composition may be packaged and commercialized alone or together with a base product such that the end-user may use same to obtain the cannabis-infused product. The cannabis-infused product can be used for medical purposes or recreational purposes.
[0021] As used herein, the term “product base” refers to dry, semi-dry or liquid composition, which is used to obtain the herein described cannabis-infused product. For example, the product base may be a finished product to which the cannabinoid composition is added to (e.g., sprinkled upon, added to, incorporated into, etc.) to obtain the cannabis-infused product. Alternatively, the product base may be an ingredient or a mixture of ingredients for making the cannabis-infused product. In such embodiment, the cannabinoid composition can be mixed with the product base to obtain a blend, which can then be used for manufacturing the cannabis-infused product by further processing (e.g., baking, cooking, extruding, pressing, homogenizing, etc.).
[0022] As used herein, the term “cannabis-infused product” refers to commercial solid, semisolid, or liquid products containing a cannabinoid for which it is desirable to reduce the cannabis- associated bitterness or off-taste. For example, cannabis-infused products, such as beverages (e.g., alcoholic, non-alcoholic, juices, sparkling water, etc.), non-beverage liquid products (oral sprays, drops, etc.), human edibles (e.g., baked goods, cereals, etc.), pet edibles (e.g., pet food, pet chew, etc.), cosmetics (balms, etc.), and/or confections (e.g., lozenges, chewing gum, mints, chocolates, candies, gummies, etc.).
[0023] As consumers demand a faster onset, emulsions used in cannabis-infused products have tended toward smaller particle sizes, typically on the nanometer scale. This is because emulsions with small particle sizes are known to correlate with fast-onset user experience. Upon placing cannabis-infused products in a user’s oral cavity (e.g., to eat, drink or apply to oral cavity surfaces such as lips), however, such small particle sizes are believed to cause bitterness and/or off-taste. Indeed, without wishing to be bound by theory, it is believed that as the size of the particles in the emulsion decreases, the apparent surface area of the particles in the emulsion that is eventually exposed to taste receptors increases, correlating to an increase in the bitter and off-taste of the cannabis-infused product.
[0024] Without being bound by any theory, it is believed that loading the emulsion in the solid carrier described herein offers several technical advantages. For example, as the emulsion is loaded within the internal porous network of the carrier, it is believed that this creates a physical barrier between the emulsion containing the cannabinoid component and the aqueous environment in the user’s mouth (saliva). Such physical barrier thus minimizes exposure of the emulsion to the user’s taste buds. For example, when the cannabinoid composition is incorporated into an edible cannabis-infused product, the cannabinoid composition is effectively locked into the cannabis-infused product food matrix while a consumer is masticating. Without wishing to be bound by theory, it is believed that the solid matrix of the edible product substantially “protects” the emulsion at the time the edible product is consumed by the user (e.g., chewed) from being significantly released from the carrier, such that the edible product is not associated with a bitter or off-taste. It is only as the matrix of the edible is more fully broken down in the gastrointestinal tract that the emulsion is effectively released from the carrier in the form of a nanoemulsion. Also, as the emulsion released is a nanoemulsion, the herein described cannabis- infused product affords the desired fast onset of the cannabinoid. This confers “taste masking” properties to the cannabinoid composition and thus the user perceives less bitterness and/or off- taste when consuming the cannabis-infused product. Other possible benefits include oxidation protection and compatibility with oil and aqueous loads.
[0025] The resulting cannabinoid composition can thus be used as an ingredient for manufacturing cannabis-infused products or any other application requiring a solid form of cannabinoids. Further, this also allows obtaining a fast cannabinoid effect onset in a wider variety of cannabis-infused products with acceptable taste.
Cannabinoid Component
[0026] The cannabinoid compositions of the present disclosure include a “cannabinoid component” that includes a cannabinoid.
[0027] As used herein, the term “cannabinoid” is generally understood to include any chemical compound that acts upon a cannabinoid receptor. Cannabinoids are commonly used for recreational purposes to produce physiological effects associated with a feeling of physical and/or emotional satisfaction. Cannabinoids can also be useful in the treatment and/or prophylaxis of a wide variety of diseases or conditions, such as pain, anxiety, inflammation, autoimmune diseases, neurological disorder, psychiatric disorder, malignancy, metabolic disorder, nutritional deficiency, infectious disease, gastrointestinal disorder, or cardiovascular disorder. Cannabinoids may also have application as neuroprotectants, for example, in limiting neurological damage following ischemic insults, such as stroke and trauma, or in the treatment of neurodegenerative diseases such as Alzheimer’s disease, Parkinson’s disease and HIV dementia. Cannabinoids for inclusion in the compositions of the present disclosure include phytocannabinoids (i.e., found in cannabis and some other plants) and synthetic cannabinoids (i.e., manufactured artificially).
[0028] Cannabinoids may be obtained from any suitable source material including, but not limited to, cannabis or hemp plant material (e.g., flowers, seeds, trichomes, and kief from cannabis plants) or manufactured (for example cannabinoids produced in yeast, for example as described in WO WO2018/148848). The term “cannabis plant(s)” encompasses wild type Cannabis (including but not limited to the species Cannabis sativa, Cannabis indica and Cannabis ruderalis) and also variants thereof, including cannabis chemovars (or “strains”) that naturally contain different amounts of the individual cannabinoids.
[0029] In some embodiments, the cannabinoid is obtained from a cannabis extract (e.g., resin, wax, concentrate, and distillate).
[0030] As used herein, a “cannabis extract” refers to an extract obtained from a cannabis plant material according to any procedure known in the art; such extracts yield cannabinoids in pure or isolated form. For example, a cannabis extract may be obtained by a process including an extraction step from plant materials using for example organic solvent extraction, such as extraction with CO2, butane, ethanol, and the like. For example, a cannabis extract may be obtained by a process including an extraction step from plant materials using for example heat decarboxylation to convert cannabinoids in their acid forms to neutral forms followed by or after CO2 extraction (under sub-critical or super-critical conditions), providing a crude extract. The crude extract may then be “winterized,” that is, extracted with ethanol to remove lipids and waxes, as described for example in US 7,700,368, US 2004/0049059, and US 2008/0167483, which are incorporated herein by reference. Optionally, the method for obtaining the cannabis extract may further include purification steps such as a distillation step to further purify, isolate, or crystallize one or more cannabinoids, which is referred to herein as a “distillate”; US20160346339, which is incorporated herein by reference, describes a process for extracting cannabinoids from cannabis plant material using solvent extraction followed by filtration, and evaporation of the solvent in a distiller to obtain a distillate. The distillate may be further cut with one or more terpenes. The distillate may be further purified, for example using chromatographic and other separation methods known in the art, to obtain an “isolate.” In some embodiments, pure or isolated cannabinoids, such as those provided in a cannabis extract, may be combined with water, lipids, hydrocarbons, ethanol or mixtures thereof.
[0031] The cannabinoid may be an isolated cannabinoid, such as a cannabis extract, having >75% purity (as in the case of a crude extract), or > 80% purity (as in the case of a distillate), or >95% purity (as in the case of an isolate). For example, and without wishing to be limiting, the cannabinoid may have a purity such as > 75%, or > 80%, or > 90%, or > 95%, or > 98%, or > 98%, or > 99%, or > 99.5%.
[0032] Examples of cannabinoids include, but are not limited to, cannabichromanon (CBCN), cannabichromene (CBC), cannabichromevarin (CBCV), cannabicitran (CBT), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabidiol (CBD, as described below), cannabidiolic acid (CBDA) cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidiorcol (CBD- C1), cannabidiphorol (CBDP), cannabidivarin (CBDV), cannabielsoin (CBE), cannabifuran (CBF), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerolic acid (CBGA), cannabigerovarin (CBGV), cannabinodiol (CBND), cannabinodivarin (CBVD), cannabinol (CBN), cannabinol methylether (CBNM), cannabinol propyl variant (CBNV), cannabinol-C2 (CBN-C2), cannabinol-C4 (CBN-C4), cannabiorcol (CBN-C1), cannabiripsol (CBR), cannabitriol (CBO), cannabitriolvarin (CBTV), cannabivarin (CBV), dehydrocannabifuran (DCBF), A7-cis-iso tetrahydrocannabivarin, tetrahydrocannabinol (THC, as described below), A9- tetrahydrocannabinol-C4 (THC-C4), A9-tetrahydrocannabinolic acid-C4 (THCA-C4), A9- tetrahydrocannabinolic acid A (THCA-A), A9-tetrahydrocannabionolic acid B (THCA-B), A9- tetrahydrocannabiorcol (THC-C1), A9-tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), ethoxy-cannabitriolvarin (CBTVE), trihydroxy-A9-tetrahydrocannabinol (triOH- THC), 10-ethoxy-9hydroxy-A6a-tetrahydrocannabinol, 8,9-dihydroxy-A6a-tetrahydrocannabinol, 10-oxo-A6a-tetrahydrocannabionol (OTHC), 3,4,5,6-tetrahydro-7-hydroxy-a-a -2-trimethyl-9-n- propyl-2, 6-methano-2H-1-benzoxocin-5-methanol (OH-iso-HHCV), A6a,10a- tetrahydrocannabinol (A6a,10a-THC), A8-tetrahydrocannabivarin (A8-THCV), A9- tetrahydrocannabiphorol (A9-THCP), A9-tetrahydrocannabutol (A9-THCB), derivatives of any thereof, and combinations thereof. Further examples of suitable cannabinoids are discussed in at least WO2017/190249 and US 2014/0271940, which are incorporated by reference in their entirety.
[0033] Examples of synthetic cannabinoids include, but are not limited to, naphthoylindoles, naphthylmethylindoles, naphthoylpyrroles, naphthylmethylindenes, phenylacetylindoles, cyclohexylphenols, tetramethylcyclopropylindoles, adamantoylindoles, indazole carboxamides, quinolinyl esters, and combinations thereof.
[0034] Cannabidiol (CBD) means one or more of the following compounds: A5-cannabidiol (2- (6-isopropenyl-3-methyl-5-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A4-cannabidiol (2-(6- isopropenyl-3-methyl-4-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A3-cannabidiol (2-(6- isopropenyl-3-methyl-3-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A3J-cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-l-yl)-5-pentyl-l,3-benzenediol); A2-cannabidiol (2-(6- isopropenyl-3-methyl-2-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A1-cannabidiol (2-(6- isopropenyl-3-methyl-l-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); and A6-cannabidiol (2-(6- isopropenyl-3-methyl-6-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol). In a preferred embodiment, and unless otherwise stated, CBD means A2-cannabidiol.
[0035] Tetrahydrocannabinol (THC) means one or more of the following compounds: A8- tetrahydrocannabinol (A8-THC), A9-cis-tetrahydrocannabinol (cis-THC), and A9- tetrahydrocannabinol (A9-THC). In a preferred embodiment, and unless otherwise stated, THC means one or more of the following compounds: A9- tetrahydrocannabinol and A8- tetrahydrocannabinol.
[0036] A cannabinoid may be in an acid form or a non-acid form, the latter also being referred to as the decarboxylated form since the non-acid form can be generated by decarboxylating the acid form. Within the context of the present disclosure, where reference is made to a specific cannabinoid, the cannabinoid can be in its acid or non-acid form or be a mixture of both acid and non-acid forms.
[0037] The cannabinoid component may include a single cannabinoid or may include a combination of two or more cannabinoids. In a non-limiting example, the cannabinoid component includes cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
[0038] As is known in the art, various cannabinoids can be used in combination to achieve a desired effect in a user. Certain specific ratios of cannabinoids may be useful to produce the feeling of physical and/or emotional satisfaction and/or may be useful in the treatment or management of specific diseases or conditions.
[0039] In some embodiments, the cannabinoid component includes a mixture of THC and CBD. The w/w ratio of THC to CBD in the cannabinoid component may be between about 1:1000 and about 1000:1. Preferably, the (w/w) ratio of THC to CBD in the component may be about 1:1000, about 1 :900, about 1 :800, about 1 :700, about 1 :600, about 1 :500, about 1 :400, about 1 :300, about 1:250, about 1:200, about 1:150, about 1:100, about 1:90, about 1:80, about 1:70, about 1:60, about 1:50, about 1:45, about 1:40, about 1:35, about 1:30, about 1:29, about 1:28, about 1:27, about 1:26, about 1:25, about 1:24, about 1:23, about 1:22, about 1:21, about 1:20, about 1:19, about 1:18, about 1:17, about 1:16, about 1:15, about 1:14, about 1:13, about 1:12, about 1:11, about 1:10, about 1:9, about 1:8, about 1:7, about 1:6, about 1:5, about 1:4.5, about 1:4, about
1 :3.5, about 1 :3, about 1 :2.9, about 1 :2.8, about 1 :2.7, about 1 :2.6, about 1 :2.5, about 1 :2.4, about 1:2.3, about 1 :2.2, about 1:2.1, about 1 :2, about 1:1.9, about 1:1.8, about 1:1.7, about 1:1.6, about 1:1.5, about 1:1.4, about 1:1.3, about 1:1.2, about 1:1.1, about 1:1, about 1.1:1, about 1.2:1, about 1.3:1 , about 1.4:1 , about 1.5:1 , about 1.6:1 , about 1.7:1 , about 1.8:1 , about 1.9:1 , about 2:1 , about 2.1 :1 , about 2.2:1 , about 2.3:1 , about 2.4:1 , about 2.5:1 , about 2.6:1 , about 2.7:1 , about 2.8:1 , about 2.9:1 , about 3: 1 , about 3.5:1 , about 4: 1 , about 4.5: 1 , about 5: 1 , about 6: 1 , about 7:1 , about 8:1 , about 9:1 , about 10:1 , about 11 :1 , about 12:1 , about 13:1 , about 14:1 , about 15:1 , about 16:1 , about 17:1 , about 18:1 , about 19:1 , about 20:1 , about 21 :1 , about 22:1 , about 23:1 , about 24:1 , about 25:1 , about 26:1 , about 27:1 , about 28:1 , about 29:1 , about 30:1 , about 35:1 , about 40:1 , about 45: 1 , about 50: 1 , about 60: 1 , about 70: 1 , about 80: 1 , about 90: 1 , about 100: 1 , about 150: 1 , about 200: 1 , about 250: 1 , about 300: 1 , about 400: 1 , about 500: 1 , about 600: 1 , about 700: 1 , about 800:1 , or about 900:1.
[0040] In some embodiments, the cannabinoid component includes the cannabinoid in a concentration of at least about 0.001 mg/g. In a non-limiting example, the cannabinoid component may comprise the cannabinoid in an amount of from about 0.001 mg/g to about 100 mg/g, including any amount therebetween or any ranges therein. For example, and without wishing to be limiting, the cannabinoid component may comprise the cannabinoid in an amount of from about 0.002 mg/g to about 100 mg/g, from about 0.1 mg/g to about 75 mg/g, or from about 0.1 mg/g to about 50 mg/g, including any amount therebetween or any ranges therein.
[0041] In some embodiments, the cannabinoid component includes the cannabinoid in an amount of from about 1 wt.% to about 25 wt.% (the weight percentage being of the cannabinoid relative to total weight of the cannabinoid component), including any amount therebetween or any ranges therein. For example, the cannabinoid component includes the cannabinoid in an amount of from about 2.5 wt.% to about 15 wt.%, including any amount therebetween or any ranges therein, such as from about 5 wt.% to about 7.5 wt.% or from about 7.5 wt.% to about 15 wt.%, including any amount therebetween or any ranges therein.
[0042] In some embodiments, the cannabinoid component may comprise other ingredients, including but not limited to one ore more carrier oils, one or more terpenes, or any combination thereof.
[0043] As used herein, the term “carrier oil” refers to medium chain triglycerides (MCT, comprising chains of between 6 and 12 carbon atoms), long chain triglycerides (LCT, comprising chains of between 13 to 21 carbon atoms), a combination thereof, or any other suitable carrier oil. Non-limiting examples of carrier oils include: borage oil, coconut oil, cottonseed oil, soybean oil, safflower oil, sunflower oil, corn oil, olive oil, palm oil, peanut oil, almond oil, sesame oil, rapeseed oil, peppermint oil, poppy seed oil, canola oil, palm kernel oil, hydrogenated soybean oil, hydrogenated vegetable oils, glyceryl esters of saturated fatty acids, glyceryl behenate, glyceryl distearate, glyceryl isostearate, glyceryl laurate, glyceryl monooleate (e.g., Peceol™), glyceryl, monolinoleate, glyceryl palmitate, glyceryl palmitostearate, glyceryl ricinoleate, glyceryl stearate, polyglyceryl 10-oleate, polyglyceryl 3-oleate, polyglyceryl 4-oleate, polyglyceryl 10-tetralinoleate, behenic acid, or any combinations thereof.
[0044] As used herein, the term “terpenes” refers to refer to a class of chemical components comprised of the fundamental building block of isoprene, which can be linked to form linear structures or rings. Terpenes may include hemiterpenes (single isoprenoid unit), monoterpenes (two units), sesquiterpenes (three units), diterpenes (four units), sesterterpenes (five units), triterpenes (six units), and so on. At least some terpenes are expected to interact with, and potentiate the activity of, cannabinoids. Examples of terpenes known to be extractable from cannabis include aromadendrene, bergamottin, bergamotol, bisabolene, borneol, 4-3-carene, caryophyllene, cineole/eucalyptol, p-cymene, dihydroj asmone, elemene, farnesene, fenchol, geranylacetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, nerylacetate, neomenthylacetate, ocimene, perillylalcohol, phellandrene, pinene, pulegone, sabinene, terpinene, terpineol, 4-terpineol, terpinolene, and derivatives thereof. Additional examples of terpenes include nerolidol, phytol, geraniol, alpha-bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, beta-amyrin, thujone, citronellol, 1 ,8-cineole, cycloartenol, and derivatives thereof.
[0045] The reader will readily understand that in some embodiments, the cannabinoid component may include other ingredients in addition to the above described additional ingredients.
[0046] In some embodiments, the cannabinoid component includes the carrier oil in an amount required to achieve a desired cannabinoid and/or carrier oil concentration(s), whether that be in the cannabinoid component, the emulsion, the composition, or the cannabis-infused product.
[0047] For example, the cannabinoid component may include the carrier oil in an amount of from about 1 wt.% to about 25 wt.% (the weight percentage being of the carrier oil relative to total weight of the cannabinoid component), including any amount therebetween or any ranges therein. For example, the cannabinoid component may include the carrier oil in an amount of from about 2.5 wt.% to about 15 wt.%, including any amount therebetween or any ranges therein, such as from about 5 wt.% to about 7.5 wt.% or from about 7.5 wt.% to about 15 wt.%, including any amount therebetween or any ranges therein, based on the total weight of the cannabinoid component.
[0048] For example, the cannabinoid component may include the carrier oil in an amount such as to allow incorporating an amount of cannabinoid into the cannabinoid component of from about 0.001 mg/g to about 100 mg/g, including any amount therebetween or any ranges therein. For example, and without wishing to be limiting, the cannabinoid component may include the carrier oil in an amount such as to allow incorporating an amount of cannabinoid into the cannabinoid component of from about 0.002 mg/g to about 100 mg/g, from about 0.1 mg/g to about 75 mg/g, or from about 0.1 mg/g to about 50 mg/g, including any amount therebetween or any ranges therein.
Emulsion
[0049] The cannabinoid component in the composition of the present disclosure is provided in an emulsion.
[0050] As used herein, the term “emulsion” includes a nanoemulsion, a microemulsion, or both.
[0051] As used herein, the term “nanoemulsion” refers to a kinetically stabilized emulsion with nanometer to micrometer sized particles. Nanoemulsions typically comprise an oil phase, a water phase, and an emulsifier - though additional components may be included. Generally, a high energy input is required to break the emulsion particles into the desired size, however selfemulsifying nanoemulsions are known in the art. Generally, nanoemulsions are known in the art, and several patent and non-patent literature is available to the person of skill. For example, nanoemulsions containing a cannabinoid are disclosed in US 2016/0081927, US 2017/0232210, WO2016/147186, WO2016144376, WO2017072762, and US 2015/0164846, each of which is hereby incorporated by reference. Nanoemulsions can be characterized by a particle size distribution (PSD) and/or polydispersity index (PDI), as further described below.
[0052] As used herein, the term “microemulsion” refers to clear, thermodynamically stable biphasic mixtures of immiscible liquids stabilized by surfactants (and optionally other compounds) (e.g., WO2015/044335, or Tartaro et al., Nanomaterials 2020, 10, 1657; doi:10.3390/nano10091657, each of which is hereby incorporated by reference). In a microemulsion, the components are miscible and form an isotropic bi-continuous system, where hydrophobic and hydrophilic domains are in a stable dynamic state of flux. Without wishing to be limiting, they may be mixtures of a water phase and an oil phase that are stabilized by an emulsifier (also called “surfactant”), which preferentially adsorbs to the oil and water interface, thereby reducing the oil droplet surface tension. Co-surfactants and co-solvents may also be included in the microemulsion. Microemulsions cannot be characterized by a PSD and/or PDI, as further described below, as there are no droplet particles that are formed initially. It is only when a microemulsion is contacted with an aqueous medium that it spontaneous generates oil droplets in the nanometer size range. Generally, any microemulsion formulations known in the art and suitable for incorporation of a cannabinoid component can be used in the compositions as described herein.
[0053] Compared to microemulsions, nanoemulsions typically include a smaller amount of emulsifiers, as further described below.
[0054] It is worth noting that in some references of the prior art, the present inventors believe that there has been confusion regarding microemulsions and nanoemulsions, likely resulting from the prefixes “micro” and “nano”. Applying known nomenclature to the context of an emulsion, and without wishing to be bound by theory, these two prefixes would give the impression to reference a specific emulsion particle size range. However, in the context of emulsions and as used herein, the difference between microemulsions and nanoemulsions is more fundamental and structural, and is unrelated to the particle size of an emulsion.
[0055] “Particle size distribution” or “PSD” is an index (means of expression) indicating what sizes (particle size) of particles are present in what proportions (relative particle amount as a percentage where the total amount of particles is 100 %) in the sample particle group to be measured. Volume, area, length, and quantity are used as standards (dimensions) for particle amount. However, generally, the volume standard is used and expressed as the diameter of the particle. The PSD is a volume-based particle size measured, for example, by dynamic light scattering (DLS) methods. It will be readily appreciated that the PSD of the cannabinoid emulsion refers to the PSD of the carrier oil droplets (as particles containing the solubilized cannabinoids) that are present in an aqueous solution.
[0056] When PSD of an emulsion is measured, it is expressed as a distribution of particle sizes. The polydispersity index (PDI) is a reflection of how monodisperse a population with a given PSD is; a lower PDI means that the majority of particles have the same PSD, while a higher PDI means that particles have a wide range of PSD possibly indicating a multimodal particle size distribution. As used herein, the term “polydispersity index” or “PDI” refers to a number calculated from a simple 2 parameter fit to the correlation data (the cumulants analysis). The PDI is dimensionless and scaled such that values smaller than 0.05 are seen with highly monodisperse standards. Values greater than 0.7 indicate that the sample has a very broad size distribution. The various size distribution algorithms work with data that fall between these two extremes. The calculations for these parameters are defined in the ISO standard document 13321 :1996 E and ISO 22412:2008.
[0057] It is also important to note that it is particularly challenging to maintain PSD for oil-in-water emulsions containing the cannabinoids. Without wishing to be bound by theory this is primarily due to the effect called Ostwald Ripening. Ostwald Ripening is the phenomena often found in oil- in-water emulsions in which large oil particles grow at the expense of smaller oil particles in solution by spontaneously absorbing onto larger oil particles to reach a more thermodynamically stable state wherein the surface area to volume ratio is minimized. The combination of destabilization by oil droplet collisions and coalescence, in addition to Ostwald Ripening in the case of volatile oils, can lead to the oil phase eventually becoming one large droplet to lower surface energy and minimize total surface area. When this occurs, over time the emulsion becomes unstable and eventually exhibit phase separation.
[0058] As discussed previously, the emulsion loaded in the carrier can be a nanoemulsion or a microemulsion. In the former case, the emulsion loaded in the carrier is generally formulated as an oil-in-water emulsion having a particle size distribution (PSD). In the latter case, the microemulsion loaded into the carrier does not have a PSD (as there are no droplets formed) and it is only when the microemulsion is contacted with an aqueous medium (e.g., when the cannabis- infused product is in a user’s Gl tract, or when the cannabinoid composition is added to a waterbased product base) that a nanoemulsion with a PSD is released therefrom.
[0059] In some embodiments, the nanoemulsion (i.e. , as loaded in the carrier and/or released from the microemulsion) has a PSD of between about 1 nm and about 999 nm (where the size is the hydrodynamic diameter), including any amount therebetween or any ranges therein. For example, the PSD can be of between about 5 nm and about 500 nm, including any amount therebetween or any ranges therein, in some cases between about 10 nm and about 250 nm, including any amount therebetween or any ranges therein, in some cases between about 25 nm and about 125 nm, including any amount therebetween or any ranges therein. For example, the nanoemulsion can be made of at least 95%, or at least 96%, or at least 97%, or at least 98%, or at least 99% of particles in the nanometric range (i.e. , from 1 to 999 nm).
[0060] In one embodiment, the nanoemulsion (i.e., as loaded in the carrier and/or the released from the microemulsion) has a PDI of less than about 35%, in some cases less than about 34%, in some cases less than about 33%, in some cases less than about 32%, in some cases less than about 31%, in some cases less than about30%, in some cases less than about 29%, in some cases less than about 28%, in some cases less than about 26%, in some cases less than about 25%, in some cases less than about 24%, in some cases less than about 23%, in some cases less than about 22%, in some cases less than about 21 %, in some cases less than about 20%, in some cases less than about 19%, in some cases less than about 18%, in some cases less than about 17%, in some cases less than about 16%, in some cases less than about 15%, in some cases less than about 14%, in some cases less than about 13%, in some cases less than about 12%, in some cases less than about 11 %, in some cases less than about 10%, and in some cases even less. Within the context of the present disclosure, the PDI is a measure of the heterogeneity of a sample of the cannabinoid composition in the form of an emulsion based on the size of the droplets of the emulsion. International standards organizations (ISOs) have established that PDI values < 5% are more common to monodisperse samples, while PDI values > 70% are common to a broad size (e.g., polydisperse) samples (see, e.g., ISO standards ISO 22,412:2017 and ISO 22,412:2017).
[0061] In one embodiment, the emulsion is a nanoemulsion and includes water in an amount of from about 50 wt.% to about 90 wt.% (weight of the water relative to emulsion weight), including any amount therebetween or any ranges therein, in some cases from about 55 wt.% to about 85 wt.%, including any amount therebetween or any ranges therein, in some cases from about 60 wt.% to about 80 wt.%, including any amount therebetween or any ranges therein.
[0062] In one embodiment, the emulsion is a microemulsion and includes minimal amounts of water. For example, microemulsions may typically include about 10 wt.% of water therein, sometimes even less.
[0063] In one embodiment, the at least one cannabinoid is present in the emulsion at a concentration, per total volume of the emulsion, up to about 1 g/ml, in some cases up to about 750 mg/ml, in some cases up to about 700 mg/ml, in some cases up to about 650 mg/ml, in some cases up to about 600 mg/ml, in some cases up to about 550 mg/ml, in some cases up to about 500 mg/L, in some cases up to about 450 mg/ml, in some cases up to about 400 mg/ml, in some cases up to about 350 mg/ml, in some cases up to about 300 mg/ml, in some cases up to about 250 mg/mL, in some cases up to about 200 mg/ml, in some cases up to about 150 mg/ml, in some cases up to about 100 mg/ml, in some cases up to about 50 mg/ml, in some cases up to about 40 mg/ml, in some cases up to about 35 mg/ml, in some cases up to about 30 mg/ml, in some cases up to about 25 mg/ml, in some cases up to about 20 mg/ml, in some cases up to about 15 mg/ml, in some cases up to about 10 mg/ml, in some cases up to about 10 mg/ml, in some cases up to about 5 mg/ml, in some cases up to about 2.5 mg/ml, in some cases up to about 1 mg/ml and in some cases even less.
Emulsifier
[0064] The emulsion in the cannabinoid composition of the present disclosure also comprises at least one emulsifier. As described above, the emulsion in the cannabinoid composition of the present disclosure may be any suitable nanoemulsion or microemulsion and as such any suitable emulsifier, co-emulsifier or co-solvent, as the case may be, can be used.
[0065] As known by the person skilled in the art, suitable emulsifiers may include but are not limited to gum arabic; polysorbates such as Tween™ 20 (polyoxyethylene sorbitan monolaurate), Tween 40 (polyoxyethylene sorbitan monopalmitate), Tween 60 (polyoxyethylene sorbitan monostearate), Tween 40 (polyoxyethylene sorbitan monopalmitate), Tween 60 (polyoxyethylene sorbitan monostearate), and Tween 80 (polyoxyethylene sorbitan monooleate); sugar esters such as sucrose monopalmitate, sucrose monostearate, sucrose distearate, sucrose polystearate, and sucrose laurate; quillaja saponin (Q-Naturale™) and components thereof; sorbitan esters (Spans™) such as Span 20 (sorbitan monolaurate), Span 40 (sorbitan monopalmitate), Span 60 (sorbitan monostearate), Span 80 (sorbitan monooleate); amphiphilic block copolymers; cholesterol; egg yolk- and soy-derived phosphatidylcholines; or any combination thereof. The person skilled in the art would be familiar with formulating cannabinoid emulsions and would be aware of suitable amounts/ratios of the at least one emulsifier.
Carrier in particulate form
[0066] The cannabinoid compositions of the present disclosure also comprise a carrier in particulate form, which has a mesoporous internal network. [0067] The carrier is inert - that is, the carrier is chemically non-reactive - and solid. The carrier may be further characterized in several ways. The carrier may be characterized by its water solubility (soluble vs. insoluble), by size parameters of its mesoporous internal network, by its application (food carrier, pharmaceutical carrier, etc.), and by its class (i.e., by the chemical composition of the carrier, or the compound from which the carrier is derived, etc.).
[0068] As used herein, the term “mesoporous internal network” refers to the presence of internal cavities I pores within the particles of the carrier, the internal cavities I pores having a diameter for example of between about 2 nm and about 1 pm, including any amount therebetween or any ranges therein, according to IIIPAC nomenclature. In some cases, the choice of one carrier over another may be dictated by the PSD of the nanoemulsion that is loaded in the carrier. For example, when loading a nanoemulsion having a PSD of from 50 nm to 150 nm, the carrier should have internal cavities I pores that can accommodate the droplet size, e.g. having internal cavities I pores with a diameter of at least 200 nm.
[0069] In some embodiments, the carrier is a water-soluble carrier. A water-soluble carrier may be particularly useful for loading microemulsions having low water content. Indeed, as discussed above, microemulsions typically include minimal amounts of water which allows one to mix the solid carrier with the microemulsion without incurring the risk of dissolving the carrier. Watersoluble carriers are therefore not compatible when using nanoemulsions that relatively have higher contents of water, as such nanoemulsions will dissolve the carrier. Nanoemulsions are predominantly water based, and as such are difficult to load on soluble carriers, which results in partial solubilization of what was intended to be the carrier matrix. This often leads to pastes and clumping exhibiting poor flow properties. This is differentiated from plating in which the carrier is only partially solubilized by water, leading to controlled aggregation/agglomeration. This is the case for many starches. For this reason, nanoemulsions have the best compatibility with insoluble carriers and are loaded through capillary diffusion.
[0070] Microemulsions are predominantly oil based (including surfactants), as such they will not solubilize water soluble carriers. This renders them compatible with both soluble and insoluble carriers. Depending on the carrier they can be loaded via capillary diffusion or through plating/agglomeration methods.
[0071] For example, the water-soluble carrier may be a food carrier derived from sugar, starch, fiber and the likes. For example, the carrier is Fibersol(B^2AG from ADM / Matsutani LLC, Promitor® from from Tate & Lyle PLC, Orafti® from Beneo GmbH, Star-Dri® 100 from Tate & Lyle PLC, FlowLac® 100 from Meggle, CAPSUL® or CAPSUL® TA from Ingredion Incorporated, N- Lok® from Ingredion Incorporated or N-Zorbit™ M from Ingredion Incorporated.
[0072] For example, the water-soluble carrier may be a pharmaceutical carrier, where the chemical composition of the carrier is hydroxypropyl cellulose (HPC). For example, the carrier is HPC SSL grade or M grade.
[0073] In some embodiment, the carrier is a water-insoluble carrier.
[0074] For example, the water-insoluble carrier can be a food carrier derived from starch, fiber and the likes. For example, the carrier is N-Zorbit™ 2144 from Ingredion Incorporated, HI-CAP® 100 from Ingredion Incorporated, Mira- Mi st® from Tate & Lyle PLC, superior potato starch from KMC or Citri-Fi 100M40 from Fiberstar Inc.
[0075] For example, the water-insoluble carrier can be an insoluble pharmaceutical carrier, where the chemical composition of the carrier comprises cyclodextrin, tricalcium phosphate, carboxymethylcellulose sodium, sodium starch gluconate, croscarmellose sodium, silicon dioxide and the likes, as further described below. For example, the carrier is spray-dried tricalcium phosphate TRI-CAFOS® from Chemische Fabrik Budenheim KG, Tabulose® from Roquette Freres SA, Explosol® from Roquette Freres SA, Solutab® from Roquette Freres SA or Fujisil™ from Fuji Chemical Industries USA, Inc. For example, the carrier is amorphous silica, such as but not limited to silicon dioxide. For example, the silicon dioxide is spray-dried granular silicon dioxide Fujisil™ from Fuji Chemical Industries USA, Inc., Omyapharm® from Omya International AG or Floguard from PPG Industries. Inc.
[0076] In one embodiment, the carrier is a modified starch or starch derivative. As used herein, the term “modified starch” refers to a native starch that has been subjected to a physical, enzymatic and/or chemical treatment to alter at least one of its physicochemical properties. Non limiting examples of modified starches include dextrin (INS 1400), alkaline-modified starch (INS 1402), bleached starch (INS 1403), oxidized starch (INS 1404, E1404), enzyme-treated starch (INS 1405), monostarch phosphate (INS 1410, E1410), distarch phosphate (INS 1412, E1412), acetylated starch (INS 1420, E1420), hydroxypropylated starch (INS 1440, E1440), hydroxyethyl starch, starch sodium octenyl succinate (OSA) starch (INS 1450, E1450), starch aluminium octenyl Succinate (INS 1452, E1452), cationic starch, carboxymethylated starch, phosphated distarch phosphate (INS 1413, E1413), acetylated distarch phosphate (INS 1414, E1414), acetylated distarch adipate (INS 1422, E1422), hydroxypropyl distarch phosphate (INS 1442, E1442), acetylated oxidized starch (INS 1451 , E1451) and the likes. The native starch may come from any suitable source, such as a plant or synthetic source. The starch derivative may be maltodextrin.
[0077] In one embodiment, the carrier can be characterized by a PSD. For example, the carrier in particulate form has a PSD of between about 1 pm and about 750 pm, including any amount therebetween or any ranges therein, in some cases between about 1 pm and about 500 pm, including any amount therebetween or any ranges therein, about 10 pm and about 250 pm, including any amount therebetween or any ranges therein.
[0078] In one embodiment, an average internal cavity I pore volume of the carrier is between about 0.5 cm3/g and about 10 cm3/g, including any amount therebetween or any ranges therein. For example, the average internal cavity I pore volume of the carrier in some cases can be between about 1 cm3/g and about 7.5 cm3/g, including any amount therebetween or any ranges therein, in some cases between about 2 cm3/g and about 5 cm3/g, including any amount therebetween or any ranges therein.
[0079] In one embodiment, the carrier has a specific surface area of between about 25 m2/g and about 1000 m2/g, including any amount therebetween or any ranges therein, in some cases between about 100 m2/g and about 750 m2/g, including any amount therebetween or any ranges therein, in some cases between about 200 m2/g and about 500 m2/g, including any amount therebetween or any ranges therein.
[0080] In some embodiments, the cannabinoid composition of the present disclosure is in a dry powder form. Within the context of the present disclosure, a “dry powder form” means that the powder has a water activity (aw) of less than 0.75, for example 0.04 < aw < 0.75, or example 0.04 < aw < 0.3. Water activity may be measured using an Aqualab Water Activity Meter 4TE (Decagon Devices, Inc., U.S.A.).
[0081] In some embodiments, the cannabinoid composition of the present disclosure is a dispersible powder. Within the context of the present disclosure, a “dispersible powder” means that the powder particles disintegrate when they are contacted with an aqueous solution.
[0082] As discussed previously, the cannabinoid composition described herein advantageously reduces the bitter and off-taste typically associated with cannabis-infused products of the prior art. Indeed, since the cannabis extract and/or emulsifiers are loaded inside the carrier internal mesoporous network, the carrier provides a physical barrier that reduces exposure of the user’s taste buds to the cannabis extract and/or emulsifiers bitter or off-taste.
[0083] This advantageous reduction in the bitter and off-taste typically associated with cannabis- infused products of the prior art is further noticeable when incorporating the cannabinoid composition described herein in edible solid or semi-solid cannabis-infused products. For example, in such cases, the carrier is incorporated within the cannabis-infused product food matrix, such that the food matrix itself further limits emulsion diffusion from the loaded carrier particles.
[0084] This advantageous technical effect can also be obtained when using the cannabinoid composition described herein in liquid cannabis-infused products (e.g., beverages, sprays, drops, etc.) with the addition of a food grade polymer shells to substantially lock in the emulsion inside the carrier. In other words, the cannabinoid composition particles can be further coated with a coating. The coating can be any suitable food grade polymer, such a but not limited to pectin, gums, chitosan or pullulan.
Loading emulsion in carrier
[0085] In one embodiment, the emulsion is loaded in the solid carrier via encapsulation. Without wishing to be bound by theory, it is believed that in this embodiment, when contacting the emulsion with the carrier the emulsion enters the mesoporous internal network of the carrier by capillary forces.
[0086] In another embodiment, the emulsion is loaded in the solid carrier via plating. In this embodiment, the emulsion is also contacted with the carrier however, the quantity of emulsion used is less than with encapsulation and the carrier is only partially solubilized. Without wishing to be bound by theory, it is believed that as the carrier comes in contact with the emulsion, the carrier particles begin to aggregate and form larger particles, such that a fraction of the emulsion enters the mesoporous internal network of the carrier by capillary forces while another fraction of the emulsion is trapped within the formed agglomerates of particles.
[0087] The person skilled in the art will readily understand that the cannabinoid composition of the present disclosure may be obtained in a number of ways. For example, a suitable quantity of the carrier may be contacted with a suitable quantity of the emulsion for a suitable period of time, which can be referred to as loading phase. For example, loading the emulsion in the carrier may include mixing the carrier with the emulsion for a time of at least 2 min, 5 min, 10 min, 15 min, or more. For example, using an amount of emulsion of from about 1 wt.% to about 80 wt.%, where the percentage is expressed relative to weight of the carrier, including any ranges there inbetween or any value therein. For example, about 2 wt.%, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, about 50 wt.%, about 55 wt.%, about 60 wt.%, about 65 wt.%, about 70 wt.%, or about 75 wt.%, including any values there in-between or any ranges with these values as extremities thereof.
[0088] Optionally, once the loading phase has been completed, the resulting mixture can be dehydrated (if desired) using any suitable technique to form a dry powder, such as but not limited to heating (e.g., in an oven), drying using a fluidized bed and the likes, and which can be referred to as the drying phase.
[0089] In one embodiment, the cannabinoid composition of the present disclosure exhibits a shelf-life stability of at least one week, preferably at least 2 weeks, preferably at least 3 weeks, preferably at least 1 month, preferably at least 1.5 months, preferably at least 2 months, preferably at least 4 months, preferably at least 6 months and in some cases even more under storage conditions of about 20°C, preferably about 30°C, preferably about 40°C and in some cases even more.
[0090] As used herein, the term “shelf-life stability” refers to the propensity of the cannabinoid composition to sufficiently stabilize the emulsion loaded therein such that after a prescribed period of time (e.g., during storage, shipping, etc.), when contacted with an aqueous solution, the cannabinoid composition releases a nanoemulsion exhibiting a desired PSD and/or a PDI. In the case of a nanoemulsion having been loaded in the carrier, the PSD and/or PDI can further remain substantially the same as the PSD and/or the PDI of the emulsion loaded in the carrier.
[0091] Within the context of the present disclosure “substantially similar” means that the PSD and/or the PDI do not vary from the desired value by more than about 15%, in some cases by more than about 12.5%, in some cases by more than about 10%, in some cases by more than about 7.5%, in some cases by more than about 5%, in some cases by more than about 2.5% and in some cases even less. Cannabis-infused products
[0092] In some embodiments, the cannabis-infused product is a solid or semi-solid edible product. Edible products come in many forms and can be any product that is suitable, e.g., nontoxic, for placing into the mouth of a human or animal, whether ingested, absorbed, or only chewed or sucked on and at least a portion discarded, etc. Illustrative examples of human edible products include but are not limited to confections such as chewing or bubble gums, mints, suckers, jawbreakers, lozenges, hard candies, gummy candies, taffies, and chocolates; baked goods such as muffins, brownies, cookies, crackers, and granola bars, and meal replacement bars; and dissolving strips. For example, a chewing-gum may have a hard shell (akin an Excel™ chewing-gum) or not (akin Juicy Fruit™).
[0093] In some embodiments, the cannabis-infused product is a liquid cannabis-infused product. For example, beverages, drops, tinctures or sprays.
[0094] Other examples of cannabis-infused products may include gels, creams, custard, pudding, honey, syrup, broth, soup, gelatin, yogurt, puree, jelly, sauce, liquid eggs, or salad dressing.
[0095] For example, a beverage includes, but without being limited to, drinking water, milk (both diary and non-diary), juice, a smoothie, coffee or a caffeinated beverage, tea, herbal tea, a cocoa beverage, a carbonated drink, a nitrogenated drink, an energy drink, a drinkable yogurt, a fermented beverage, or an alcoholic or non-alcoholic drink. An alcoholic or non-alcoholic drink includes but is not limited to, alcoholic or non-alcoholic beer, lager, cider, spirits, wine/fortified wine, and cocktails.
[0096] The person of skill will readily understand how to infuse a product base to obtain the herein described cannabis-infused product. As discussed previously, the cannabinoid composition can be used by its manufacturer to obtain the cannabis-infused product, ready for packaging and commercialization. In some embodiments, the cannabinoid composition may be packaged and sold to a product manufacturer, which can then use same to obtain the cannabis-infused product. In some embodiments, the cannabinoid composition may be packaged and commercialized alone or together with a base product such that the end-user may use same to obtain the cannabis- infused product. [0097] For example, in order to obtain a cannabis-infused chewing gum, one may proceed to contact and mix the chewing gum ingredients (such as gum base [e.g., elastomers, waxes, and resin], sweeteners, glycerin, plasticizer and colors) with the herein described cannabinoid composition and process the mixture to obtain the cannabis-infused chewing gum.
[0098] For example, in order to obtain a cannabis-infused muffin, one may proceed to mix the muffin ingredients (e.g., flour, sugar, milk, etc.) with the herein described cannabinoid composition and process (bake) the mixture to obtain the cannabis-infused muffin. Alternatively, the person of skill may proceed to add the herein described cannabinoid composition on top of the finished product (e.g., a muffin or a potato chip) thus sprinkling the cannabinoid composition onto the finished product.
[0099] For example, in order to obtain a cannabis-infused beverage, the cannabinoid composition manufacturer may proceed to incorporate same into a beverage base to obtain the cannabis-infused beverage. Alternatively, the cannabinoid composition may be packaged and sold to a beverage manufacturer, which can then use same to obtain the cannabis-infused product. Alternatively, the cannabinoid composition may be packaged and commercialized alone or together with a base product such that the end-user may use same to obtain the cannabis- infused product. For example, the end user may dispense the cannabinoid composition from a pouch containing same (or any other type of powder container) into a bottled beverage.
[0100] In one embodiment, the cannabis-infused product may comprise at least 0.002 mg/ml (or mg/g) of one or more cannabinoid(s). For example, the cannabis-infused product may include from 0.002 mg/ml (or mg/g) to about 1 mg/ml (or mg/g) of one or more cannabinoid(s).
[0101] In one embodiment, the cannabis-infused product is a unit, the unit comprising less than 1000 mg, or less than 900 mg, or less than 800 mg, or less than 700 mg, or less than 600 mg, or less than 500 mg, or less than 400 mg, or less than 300 mg, or less than 200 mg, or less than 100 mg, or less than 50 mg, or less than 40 mg, or less than 30 mg, or less than 20 mg, or less than 10 mg, or less than 5 mg, or less than 2.5 mg of one or more cannabinoid(s).
Use of cannabis-infused product
[0102] Cannabis-infused products are typically used for recreational and/or medicinal uses. For example, cannabis-infused products can be used to achieve a desired effect in a user, such as a psychoactive effect, a physiological effect, or a treatment of a condition. By “psychoactive effect”, it is meant a substantial effect on mood, perception, consciousness, cognition, or behavior of a subject resulting from changes in the normal functioning of the nervous system. By “physiological effect”, it is meant an effect associated with a feeling of physical and/or emotional satisfaction. By “treatment of a condition”, it is meant the treatment or alleviation of a disease or condition by absorption of cannabinoid(s) at sufficient amounts to mediate the therapeutic effects.
[0103] The terms “treating”, “treatment” and the like are used herein to mean obtaining a desired pharmacologic and/or physiologic effect. The effect may be prophylactic, in terms of completely or partially preventing a disease, condition, or symptoms thereof, and/or may be therapeutic in terms of a partial or complete cure for a disease or condition and/or adverse effect, such as a symptom, attributable to the disease or disorder. “Treatment” as used herein covers any treatment of a disease or condition of a mammal, such as a dog, cat or human, preferably a human.
[0104] In certain embodiments, the disease or condition is selected from the group consisting of pain, anxiety, an inflammatory disorder, a neurological disorder, a psychiatric disorder, a malignancy, an immune disorder, a metabolic disorder, a nutritional deficiency, an infectious disease, a gastrointestinal disorder, and a cardiovascular disorder. Preferably the disease or condition is pain. In other embodiments, the disease or condition is associated with the feeling of physical and/or emotional satisfaction.
[0105] In the context of recreational use, the “effective amount” administered and rate and timecourse of administration, will depend on the desired effect associated with a feeling of physical and/or emotional satisfaction in the subject.
[0106] In the context of health and wellness use, the “effective amount” administered and rate and time-course of administration will depend on the nature and severity of the disease or condition being treated and typically also takes into consideration the condition of the individual subject, the method of administration and the like.
EXAMPLES
[0107] The following examples are provided to further illustrate the present invention and are not to be construed as limitations of the present invention, as many variations of the present invention are possible without departing from its spirit or scope. The following examples describe some exemplary modes of making and practicing certain compositions that are described herein. These examples are for illustrative purposes only and are not meant to limit the scope of the compositions and methods described herein.
Example 1 : Cannabinoid composition - nanoemulsion
[0108] In this example, a nanoemulsion with 3 wt.% THC was prepared. The composition of the nanoemulsion is provided below in Table 1.
Table 1
Figure imgf000028_0001
[0109] The water and oil phase ingredients were solubilized separately using heat and stirring.
1. The oil phase: THC distillate and MCT carrier oil were mixed in a beaker at 80°C with medium agitation for 10 minutes. Tocobiol™ and glycerol were slowly added to the mixture, with medium agitation and heat for approximately 20 minutes.
2. The water phase: USP grade water, ethanol, and EDTA were mixed until completely dissolved (approximately 5-10 minutes). Tween™ 80 was added to the mixture and mixed at 80°C with moderate agitation for 20 minutes.
3. Once the respective water and oil phases were prepared, the oil phase was added slowly to the water phase while mixing to form an emulsion.
4. High energy sonication was applied to the emulsion of step 3 for 10 minutes using a sonicator (LSP-500 Ultrasonic Processor, Sonomechanics, Florida, USA) set to 50-80% amplitude. Example 2: Cannabinoid compositions - microemulsion
[0110] In this example, a microemulsion with 5 wt.% THC was prepared. The composition is provided below in Table 2.
Table 2
Figure imgf000029_0001
[0111] The water and oil phase ingredients were solubilized separately using heat and stirring.
1. The oil phase: THC distillate, glyceryl monooleate, and MCT carrier oil were mixed in a beaker at medium heat, with medium agitation for 10 minutes (until all mixture was homogeneous).
2. The water phase: USP grade water and Kolliphor RH 40 were mixed until completely dissolved.
3. Once the respective water and oil phases were prepared, the oil phase was added slowly to the water phase with mixing.
Example 3: Carrier loading
[0112] Various carriers were loaded with an emulsion (the nanoemulsion of Table 3 or the microemulsion of Table 2). The composition of the nanoemulsion is provided below in Table 3. Table 3
Figure imgf000030_0001
[0113] The carriers were loaded with the emulsion wt.% as shown in table 4 below.
Table 4
Figure imgf000030_0002
Example 4: PLS and hydration study - nanoemulsion
[0114] In this example, the nanoemulsion of Example 1 was loaded into a carrier to form the cannabinoid composition, which was subsequently tested in a hydration test.
[0115] To form the cannabinoid composition, the nanoemulsion of Example 1 was loaded into the carrier by mixing the carrier with the nanoemulsion for 10 minutes, thus forming the cannabinoid composition. The carriers tested include the SiC>2 insoluble powders Fujisil™ and Floguard, and the tricalcium phosphate insoluble powder Tri-CAFOS®. The carriers were loaded with 20 wt.% nanoemulsion. [0116] The hydration test included placing the cannabinoid composition (1g) into water (80g) and stirring for 1 minute. The table below also reports the capability of the cannabinoid composition to maintain the integrity of the emulsion over time, to mimic shelf-life conditions such as during storage, shipping and the like. Table 5 includes several time points (t), where each time point corresponds to the storage time of the cannabinoid composition. In other words, “t = 1 week” means that the cannabinoid composition was stored at room temperature for 1 week and then the hydration test was performed and the particle size was measured on the same day of the hydration test, whereas “t = 0” means that the hydration test was performed on the same day that the cannabinoid composition was made (i.e. , no storage time).
[0117] Measuring the particles size of the emulsion released from the cannabinoid composition was performed via Dynamic Light Scattering (DLS).
[0118] The resulting samples undergo DLS measurement to determine PSD and PDI - the resulting samples may or may not be passed through a 0.2 pm filter prior to DLS measurement, as indicated. The results are provided below in Table 5.
Table 5
Figure imgf000031_0001
[0119] The results from T able 5 show that the PSD and the PSI for the nanoemulsions released from the cannabinoid compositions using Fujisil™, Floguard and Tri-CAFOS® as a carrier do not substantially change after 1 week, after 2 weeks and after 4 weeks storage of the cannabinoid composition at room temperature. Example 5: PLS hydration study - microemulsion
[0120] In this example, the microemulsion of Example 2 was loaded into a soluble or insoluble carrier to form the cannabinoid composition, which was subsequently tested in the hydration tests as described previously.
[0121] The carriers tested include the SiC>2 insoluble powders Omyapharm®, Fujisil™ and Floguard, the tricalcium phosphate insoluble powder T ri-CAFOS® and the water-soluble modified starches N-Zorbit™ M and Mira-Mist®. The carriers were loaded with 20 wt.% microemulsion. The results are provided below in Table 6.
Table 6
Figure imgf000032_0001
[0122] The results from Table 6 show that the PSD and the PSI for the nanoemulsions released from the cannabinoid compositions using Fujisil™, Tri-CAFOS®, N-Zorbit™ M and Mira-Mist® as a carrier do not substantially change after 1 week and after 2 weeks of storage of the cannabinoid composition at room temperature. The PSD values showing two numbers as identified with * refers to a bimodal PSD where each number is for each mode in the bimodal PSD.
Example 6: Taste masking study
[0123] In this example, cannabinoid compositions containing the nanoemulsion of Table 3 was incorporated in a gummy base and the resulting cannabis-infused gummy products were submitted to a tasting test.
[0124] The composition of the gummies is shown in Table 7 below. Table 7
Figure imgf000033_0001
[0125] Various cannabinoid compositions were formulated as per the following Table 8:
Table 8
Figure imgf000033_0002
[0126] The test also included two controls; one without cannabinoid composition and one in which the nanoemulsion was incorporated directly in the gummy base (i.e., without any solid carrier). The gummies were provided to a subject who was asked to qualify both the taste and texture of the gummies and results are shown in table 9 below.
Table 9
Figure imgf000033_0003
[0127] The results show that the use of cannabinoid compositions in accordance with the present disclosure in the manufacture of cannabis-infused products results in a reduced perception of bitterness or off-taste when compared to cannabis-infused products in which a nanoemulsion is introduced directly in the cannabis-infused product base (i.e., when no solid carrier is used).
Example 7: Taste study - Nanoemulsion and microemulsions
[0128] In this example, a nanoemulsion and a microemulsion containing orange bitter oil and comparative controls were tested then infused into chocolate for taste properties.
Table 10 - Nanoemulsion 1 (NE 1) Formulation Details
Figure imgf000034_0001
[0129] The procedure for the nanoemulsion preparation was as follows: Glycerol, Tween 80 and MCT Oil were mixed in a beaker with stirring by a magnetic stirrer. Slightly heated at 65-70 °C for easy miscibility. Cooled to room temperature followed by addition of Orange bitter oil. Finally, water is added with mixing to obtain homogeneity. The procedure for white chocolate preparation with nanoemulsion I microemulsion was as follows: white chocolate was slightly heated at GOGS °C just to melt, followed by addition of the nanoemulsion I microemulsion at different ratios. Mixed thoroughly and allowed to cool and solidify.
[0130] The chocolate formulation details, and taste results are provided in the following Tables 11a and 11b: Table 11a - Chocolate Formulation Details
Figure imgf000035_0001
Table 11b - Chocolate taste results and description
Figure imgf000035_0002
[0131] The taste index is categorised as a scale of 0 - 10 to indicate bitterness (0- No bitter taste: Taste of white chocolate, and taste index increases with increase in bitterness from 1 to 10). The codes of different nanoemulsion formulations and their description is set forth in Table 11C:
Table 11C
Figure imgf000035_0003
[0132] As per the taste results from Table 11b, the dose of Orange bitter oil seems to be lower to feel sufficient bitterness, therefore the dose of orange bitter oil was increased in next formulations (nanoemulsion 2) to 100 mg per 4.5 g of total (chocolate + N/NO/O).
Table 12 - Nanoemulsion 2 (NE 2) Formulation Details
Figure imgf000036_0001
[0133] The chocolate formulation details, and taste results are provided in the following Tables 12a and 12b:
Table 12a
Figure imgf000036_0002
Table 12b
Figure imgf000037_0001
Table 13 - Microemulsion 1 (ME 1) Formulation Details
Figure imgf000037_0002
[0134] The procedure for the microemulsion preparation was as follows: Kolliphor RH 40, Maisine CC and MCT Oil were mixed in a beaker with stirring by a magnetic stirrer. Slightly heated at 65-70 °C for easy miscibility of Kolliphor RH 40. Cooled to room temperature followed by addition of Orange bitter oil and mixed for homogeneity.
[0135] The chocolate formulation details, and taste results are provided in Tables 14a and 14b:
Table 14a - Chocolate Formulation Details
Figure imgf000038_0001
Table 14b - Taste Results for Microemulsion
Figure imgf000038_0002
[0136] The codes of different microemulsion formulations and their description is set forth in
Table 14C:
Table 14C - Codes of different Microemulsion formulations and their description
Figure imgf000039_0001
[0137] As per the taste results described here, significant bitterness in chocolate formulation is noticed with a pinching and acidic effect throughout the tongue and is considered as bitterness criteria to compare with solid dispersion formulations in the following example.
Example 8: Taste study - Nanoemulsion and microemulsions loaded into solid carriers
[0138] In this example, the nanoemulsion and microemulsions of Example 7 were loaded into solid carriers and tested when infused into chocolate for taste properties.
[0139] The nanoemsulsions were loaded into Syloid 244FP, FujiSil or Syloid XDP 3050, which are different grades of Silicon dioxide with different oil adsorbing properties.
Table 15 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-001 & C-BBK-001)
Figure imgf000039_0002
Table 16 - taste results of BBK-001 & C-BBK-001
Figure imgf000040_0001
Table 17 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-002 & C-BBK-002)
Figure imgf000040_0002
Table 18 - Taste Results of BBK-002 & C-BBK-002
Figure imgf000041_0001
Table 19 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-003 & C-BBK-003
Figure imgf000041_0002
Table 20 - Taste Results of BBK-003 & C-BBK-003
Figure imgf000042_0001
[0140] The microemsulsions were loaded into Syloid 244FP, FujiSil or Syloid XDP 3050, which are different grades of Silicon dioxide with different oil adsorbing properties.
Table 21 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-004 & C-BBK-004)
Figure imgf000042_0002
Table 22 - Taste Results of BBK-004 & C-BBK-004
Figure imgf000043_0001
Table 23 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-005 & C-BBK-005)
Figure imgf000043_0002
Table 24 - Taste Results of BBK-005 & C-BBK-005
Figure imgf000044_0001
Table 25 - Solid Dispersion & Corresponding Chocolate Formulation (BBK-006 & C-BBK-006)
Figure imgf000044_0002
Table 26 - Taste Results of BBK-006 & C-BBK-006
Figure imgf000045_0001
[0141] From the results obtained in Example 7 and 8, the present inventors conclude the following:
[0142] The bitterness of orange oil is masked by different silicon dioxide carriers as revealed from the taste index and all the three different grades of silicon dioxide were found to be identical from taste masking perspective. Further, it was also observed that there is less pinching and acidic effect observed in solid dispersions as well as in chocolates containing solid dispersions; however, flavor of orange persist in all the formulations which may not be considered as bitterness. Microemulsion Without Orange oil is slightly less bitter as compared to NE without orange oil, because of tween 80 in latter case. Kolliphor RH 40 has a surfactant taste, however, is characteristic (less soapy and less tween kind). Microemulsion with orange oil and nanoemulsion with orange oil both have almost same kind of pinching and acidic effect with same after taste effect. From particle size and flowability point of view - it is of the following order: in term of flowability, the present inventors observed that Syloid XDP 3050 > FujSil > Syloid 244 FP whereas Syloid XDP 3050 and FujSil are comparable, and Syloid XDP 3050 is less in volume (denser).
[0143] Other examples of implementations will become apparent to the reader in view of the teachings of the present description and as such, will not be further described here.
[0144] Note that titles or subtitles may be used throughout the present disclosure for convenience of a reader, but in no way these should limit the scope of the invention. Moreover, certain theories may be proposed and disclosed herein; however, in no way they, whether they are right or wrong, should limit the scope of the invention so long as the invention is practiced according to the present disclosure without regard for any particular theory or scheme of action.
[0145] As used herein, articles such as “a” and “an”, are understood to mean one or more of what is claimed or described.
[0146] As used herein, the term “aqueous composition” means a composition having a liquid component that comprises at least about 10 wt.%, at least about 20 wt.%, at least about 30 wt.% or at least about 40 wt.% water, for example, based on the total weight of the composition. Suitable examples of aqueous compositions include mixtures, suspensions or emulsions, preferably emulsions.
[0147] As used herein, the terms “comprises”, “comprising”, “include”, “includes”, “including”, “contain”, “contains” and “containing” are meant to be non-limiting, i.e., other steps and other sections which do not affect the end of result can be added. The above terms encompass the terms “consisting of” and “consisting essentially of’.
[0148] As used herein, terms of degree such as “about”, “approximately” and “substantially” mean a reasonable amount of deviation of the modified term such that the end result is not significantly changed. These terms may refer to a measurable value such as an amount, a temporal duration, and the like, and are meant to encompass variations of +/- 0.1% of the given value, preferably +/- 0.5%, preferably +/- 1 %, preferably +/- 2%, preferably +/- 5% or preferably +/- 10%. [0149] As used herein, the terms “preferred”, “preferably” and variants refer to embodiments of the disclosure that afford certain benefits, under certain circumstances. However, other embodiments may also be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful and is not intended to exclude other embodiments from the scope of the disclosure.
[0150] It is understood that the test methods that are disclosed in the Test Methods Section of the present application must be used to determine the respective values of the parameters of Applicant’s disclosures as described and claimed herein.
[0151] In all embodiments of the present disclosure, all percentages, parts and ratios are based upon the total weight of the compositions of the present disclosure, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.
[0152] All references cited throughout the specification are hereby incorporated by reference in their entirety for all purposes.
[0153] Reference throughout the specification to “some embodiments”, and so forth, means that a particular element (e.g., feature, structure, and/or characteristic) described in connection with the invention is included in at least one embodiment described herein, and may or may not be present in other embodiments. In addition, it is to be understood that the described inventive features may be combined in any suitable manner in the various embodiments.
[0154] Unless otherwise defined, 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 invention pertains. In the case of conflict, the present document, including definitions will control the meaning of such terms.
[0155] As used in the present disclosure, the terms “around”, “about” or “approximately” shall generally mean within the error margin generally accepted in the art. Hence, numerical quantities given herein generally include such error margin such that the terms “around”, “about” or “approximately” can be inferred if not expressly stated. [0156] Although various embodiments of the disclosure have been described and illustrated, it will be apparent to those skilled in the art considering the present description that numerous modifications and variations can be made. The scope of the invention is defined more particularly in the appended claims.

Claims

1. A cannabinoid composition for manufacturing a cannabis-infused product, the cannabinoid composition comprising: a) an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid; and b) a carrier in particulate form comprising a mesoporous internal network, wherein the emulsion is loaded in particles of the carrier, wherein the cannabinoid composition is in the form of a powder and wherein upon contacting the cannabinoid composition with an aqueous medium, the cannabinoid composition releases a nanoemulsion.
2. The cannabinoid composition of claim 1, wherein the composition has taste-masking properties.
3. The cannabinoid composition of claim 1, wherein the cannabinoid component comprises the cannabinoid in combination with a carrier oil.
4. The cannabinoid composition of claim 3, wherein the carrier oil comprises medium-chain triglycerides (MCT), long chain triglycerides (LCT), or a combination thereof.
5. The cannabinoid composition of any one of claims 1 to 4, wherein the cannabinoid component comprises cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof.
6. The cannabinoid composition of any one of claims 1 to 5, wherein the carrier is an inert carrier.
7. The cannabinoid composition of any one of claims 1 to 6, wherein the carrier is a water soluble carrier.
8. The cannabinoid composition of any one of claims 1 to 6, wherein the carrier is a water insoluble carrier.
9. The cannabinoid composition of claim 6, wherein the carrier includes a modified starch.
48 The cannabinoid composition of claim 9, wherein the modified starch is N-Zorbit 2144. The cannabinoid composition of claim 8, wherein the carrier includes tricalcium phosphate. The cannabinoid composition of claim 8, wherein the carrier includes silicon dioxide. The cannabinoid composition of any one of claims 1 to 12, wherein the carrier has pores having a diameter of between about 2 nm and about 1 pm according to IIIPAC nomenclature. The cannabinoid composition of any one of claims 1 to 13, wherein particles of the carrier further comprise a coating on at least a portion of a surface thereof. The cannabinoid composition of claim 14, wherein the coating includes a food grade polymer. The cannabinoid composition of claim 15, wherein the food grade polymer comprises pectin, gums, chitosan or pullulan. The cannabinoid composition of any one of claims 1 to 16, wherein the emulsion is a microemulsion that releases a nanoemulsion upon the microemulsion contacting an aqueous medium. The cannabinoid composition of any one of claims 1 to 16, wherein the emulsion is a nanoemulsion. The cannabinoid composition of any one of claims 1 to 18, wherein the cannabis-infused product is a solid or semi-solid edible cannabis-infused product. The cannabinoid composition of any one of claims 1 to 18, wherein the cannabis-infused product is a liquid cannabis-infused product. The cannabinoid composition of claim 20, wherein the cannabis-infused product is in the form of a cannabis-infused beverage, a cannabis-infused drop, a cannabis-infused tincture, or a cannabis-infused spray.
49 A solid or semi-solid edible cannabis-infused product comprising the cannabinoid composition of any one of claims 1 to 18. The solid or semi-solid edible cannabis-infused product of claim 22, wherein the cannabis- infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles. A liquid cannabis-infused product comprising the cannabinoid composition of any one of claims 1 to 18. The liquid cannabis-infused product of claim 24, wherein the cannabis-infused product is selected from the group consisting of a cannabis-infused beverage, a cannabis-infused drop, a cannabis-infused tincture and a cannabis-infused spray. A method for preparing a cannabinoid composition, comprising: a) providing an emulsion comprising an emulsifier and a cannabinoid component, the cannabinoid component comprising a cannabinoid; and b) loading the emulsion in a carrier in particulate form, the carrier comprising a mesoporous internal network, wherein the cannabinoid composition is in the form of a powder. The method of claim 26, wherein the loading comprises encapsulating the emulsion in the carrier in particulate form. The method of claim 27, wherein the loading comprises plating the emulsion in the carrier in particulate form. The method of any one of claims 26 to 28, further comprising dehydrating the powder. The method of any one of claims 26 to 29, further comprising coating at least a portion of a surface of powder particles with a coating. The method of claim 30, wherein the coating includes a food grade polymer. The method of claim 31 , wherein the food grade polymer comprises pectin, gums, chitosan or pullulan.
50 The method of any one of claims 26 to 32, further comprising mixing the powder with a product base. The method of claim 33, further comprising dehydrating the powder mixed with the product base. The method of claim 33 or 34, wherein the product base is for manufacturing a solid or semi-solid edible cannabis-infused product. The method of claim 35, wherein the solid or semi-solid edible cannabis-infused product is selected from the group consisting of baked goods, confections, human edibles and pet edibles. The method of claim 33 or 34, wherein the product base is for manufacturing a liquid cannabis-infused product. The method of claim 37, wherein the liquid cannabis-infused product is selected from the group consisting of a cannabis-infused beverage, a cannabis-infused drop, a cannabis- infused tincture and a cannabis-infused spray. The method of any one of claims 26 to 38, wherein the cannabinoid composition has tastemasking properties. The method of any one of claims 26 to 39, wherein the cannabinoid component comprises the cannabinoid in combination with a carrier oil. The method of claim 40, wherein the carrier oil comprises medium-chain triglycerides (MCT), long chain triglycerides (LCT), or a combination thereof. The method of any one of claims 26 to 41 , wherein the cannabinoid component comprises cannabidiol (CBD), tetrahydrocannabinol (THC), or a mixture thereof. The method of any one of claims 26 to 42, wherein the carrier is an inert carrier. The method of claim 43, wherein the inert carrier is a water soluble carrier. The method of claim 43, wherein the inert carrier is a water insoluble carrier. The method of claim 43, wherein the carrier includes a modified starch.
51 The method of claim 46, wherein the modified starch is N-Zorbit 2144. The method of claim 45, wherein the carrier includes tricalcium phosphate. The method of claim 45, wherein the carrier includes silicon dioxide. The method of any one of claims 26 to 49, wherein the carrier has pores having a diameter of between about 2 nm and about 1 pm according to IIIPAC nomenclature. The method of any one of claims 26 to 50, wherein the emulsion is a microemulsion that releases a nanoemulsion upon the microemulsion contacting an aqueous medium. The method of any one of claims 26 to 50, wherein the emulsion is a nanoemulsion.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015068052A2 (en) * 2013-10-31 2015-05-14 Full Spectrum Laboratories, Ltd. Terpene and cannabinoid formulations
WO2020037411A1 (en) * 2018-08-20 2020-02-27 Hexo Operations Inc. Cannabinoid based emulsion systems for infused aqueous compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015068052A2 (en) * 2013-10-31 2015-05-14 Full Spectrum Laboratories, Ltd. Terpene and cannabinoid formulations
WO2020037411A1 (en) * 2018-08-20 2020-02-27 Hexo Operations Inc. Cannabinoid based emulsion systems for infused aqueous compositions
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