WO2020150661A9 - Procédé de fabrication d'huiles de monoacylglycéride et produits alimentaires contenant des huiles de monoacylglycéride - Google Patents

Procédé de fabrication d'huiles de monoacylglycéride et produits alimentaires contenant des huiles de monoacylglycéride Download PDF

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Publication number
WO2020150661A9
WO2020150661A9 PCT/US2020/014182 US2020014182W WO2020150661A9 WO 2020150661 A9 WO2020150661 A9 WO 2020150661A9 US 2020014182 W US2020014182 W US 2020014182W WO 2020150661 A9 WO2020150661 A9 WO 2020150661A9
Authority
WO
WIPO (PCT)
Prior art keywords
oil
processed oil
processed
weight
acid
Prior art date
Application number
PCT/US2020/014182
Other languages
English (en)
Other versions
WO2020150661A1 (fr
Inventor
Daniel J. Monticello
Werner J. BUSSMANN
Original Assignee
Glycosbio Food Sciences, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Glycosbio Food Sciences, Inc. filed Critical Glycosbio Food Sciences, Inc.
Priority to JP2021541037A priority Critical patent/JP2022517271A/ja
Priority to CA3127093A priority patent/CA3127093A1/fr
Priority to AU2020207945A priority patent/AU2020207945A1/en
Priority to EP20706042.7A priority patent/EP3911164A1/fr
Priority to CN202080018774.0A priority patent/CN113747796A/zh
Publication of WO2020150661A1 publication Critical patent/WO2020150661A1/fr
Publication of WO2020150661A9 publication Critical patent/WO2020150661A9/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols

Definitions

  • said steps of mixing a starting oil comprising triacylglycerols (TAGs), a buffer solution and a first enzyme capable of hydrolyzing said TAGs to free fatty acids (FFAs) and allowing said reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs to FFA are performed under a nitrogen atmosphere.
  • TAGs triacylglycerols
  • FFAs free fatty acids
  • said step of inactivating said second enzyme is performed by heating said reaction product.
  • a processed oil having a total fatty acid content comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 5% and about 75% by weight of the total fatty acid content of the processed oil composition.
  • MOG oleic acid monoglyceride
  • a method for treating type II diabetes in a subject in need thereof includes the step of administering to the subject a composition comprising a processed oil comprising oleic acid monoglyceride, wherein at least 50% by weight of said oleic acid monoglyceride is 1-oleyl monoglyceride.
  • fatty acid profiles for various starting oils are shown in Table 2 below which provides percentages of total fatty acid methyl esters (FAMEs). Nd - not determined. SAF - safflower, GRP- grape, SIL - Silynum marianum , HMP - hemp, SFL - sunflower, WHG - wheat germ, PMS - pumpkin seed, SES - sesame, RB - rice bran, ALM -almond, RPS - rapeseed (canola), PNT - peanut, OL - olive, and COC - coconut oils. Table 2 also provides the ratios of oleic acid/linoleic acid and oleic acid/linolenic acid for each oil.
  • the processed oil comprises a FFA content equal to or greater than 5% by weight of the total weight of the processed oil.
  • the processed oil comprises a MAG content of about 5% to 66%, 10% to 66%, 20% to 66%, 30% to 66%, 40% to 66%, 50 to 66%, 5% to 50%, 10% to 50%, 20% to 50%, 30% to 50%, 40% to 50%, 5% to 40%, 10% to 40%, 20% to 40%, 30% to 40%, 5% to 30%, 10% to 30%, 20% to 30%, 5% to 20%, 10% to 20%, 5% to 15%, 10% to 15%, 5% to 10% contour or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, or 66% by weight of the total weight of the processed oil.
  • Example 1 Process of making a product enriched in MAG compared to starting TAG-rich oil.
  • the method of making a product enriched in MAG compared to the starting TAG-rich oil involves 3 key steps: (1) A mild enzymatically-catalyzed reaction to hydrolyze triglycerides (TAGs) in a sequence that converts the natural oils to specific combinations of FFAs, MAGs, DAGs, and low residual TAGs; (2) an esterification with glycerol to generate predominantly high amounts of MAGs leaving low concentrations of FFAs; and (3) isolation of the modified lipid product; this is achieved by phase separation with or without the aid of a centrifuge.
  • TAGs hydrolyze triglycerides
  • FIGURE 10 depicts the serum triglyceride level averaged from 8 patients from each of Arm 1 and Arm 2 in the study over the six hour sampling period. Both the test and control groups showed similar triglyceride levels which indicate that the patients absorbed the same amount of lipid from either the standard nutritional supplement with PERT or the RTDS without PERT.
  • EMO /sunflower lecithin mixture Slowly add EMO /sunflower lecithin mixture to main mixing vessel. Add distilled water to increase volume to 95% total fluid mass, return temperature at 70+/- 2 °C . Slowly add flavors and color to main mixing vessel. Slowly add stabilizer (such as acacia gum) to main mixing vessel. Mix solution for 20 minutes (to allow the viscosity to increase). Maintain temperature of solution at 70+/- 2 °C . QS solution with distilled water to final volume. Pass material through pressure drop homogenizer(s) to produce stable emulsions. Pasteurize or sterilize material. Cool material to room temperature. Fill product into packaging.
  • stabilizer such as acacia gum
  • the food product further comprises a carbohydrate source and the carbohydrate source comprises a fruit or agave syrup.
  • said processed oil comprises a MAG content of from about 50% to about 95% by weight based on the total weight of the processed oil.
  • the MOGin said processed oil comprises at least 50% by weight 1-oleyl monoglyceride out of the total amount of MOG.
  • the processed oil further comprises linoleic acid, wherein said linoleic acid is present in said processed oil in an amount of about 20% to about 90% by weight out of the total fatty acid content of the processed oil.
  • At least a portion of said oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 60% by weight 1-oleyl monoglyceride out of the total amount of MOG.
  • MOG oleic acid monoglyceride
  • the processed oil comprises non-oil ingredients derived from and naturally present in the oil source such that the non-oil ingredients are not added to the processed oil.
  • the MOG in the processed oil comprises at least 80% by weight 1-oleyl monoglyceride out of the total amount of MOG.
  • the amount of oleic acid, linoleic acid and linolenic acid in the processed oil is within about 1% of the amount of oleic acid, linoleic acid and linolenic acid, respectively, in the pre-processed oil from which the processed oil was produced.
  • a processed oil has a fatty acid profile comprising oleic acid, linoleic acid and linolenic acid, wherein the amount of oleic acid, linoleic acid and linoleic acid in the processed oil is within about 1% of the amount of oleic acid, linoleic acid and linolenic acid, respectively, in the pre-processed oil from which the processed oil was produced, and wherein the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
  • MAGs monoacylglyceride
  • a method for treating diabetes in a subject in need thereof comprises: administering to said subject a composition comprising a processed oil comprising oleic acid monoglyceride (MOG), wherein at least 50% by weight of said MOG is 1- oleyl monoglyceride.
  • MOG oleic acid monoglyceride
  • said processed oil is a processed oil according to any one of the fifth through fourteenth embodiments and any of the foregoing aspects thereof.
  • the condition is insulin resistance or type II diabetes.
  • a processed oil comprises greater than 60% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil and having a total fatty acid content.
  • MAGs monoacylglyceride
  • a processed oil comprises greater than 90% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil and having a total fatty acid content.
  • MAGs monoacylglyceride
  • the processed oil further comprises oleic acid in amount of from about 50% to about 75% by weight out of the total fatty acid content of the processed oil.
  • the processed oil further comprises oleic acid in amount of from about 60% to about 75% by weight out of the total fatty acid content of the processed oil.
  • the processed oil further comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid is between about 10 and 100.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne des compositions et des procédés pour incorporer des huiles traitées à teneur élevée en monoacylglycéride (MAG) dans des produits et des produits alimentaires. L'invention concerne, plus particulièment, des procédés de production d'huiles traitées à teneur élevée en MAG.
PCT/US2020/014182 2019-01-18 2020-01-17 Procédé de fabrication d'huiles de monoacylglycéride et produits alimentaires contenant des huiles de monoacylglycéride WO2020150661A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2021541037A JP2022517271A (ja) 2019-01-18 2020-01-17 モノアシルグリセリド油およびモノアシルグリセリド油を含有する食品の製造方法
CA3127093A CA3127093A1 (fr) 2019-01-18 2020-01-17 Procede de fabrication d'huiles de monoacylglyceride et produits alimentaires contenant des huiles de monoacylglyceride
AU2020207945A AU2020207945A1 (en) 2019-01-18 2020-01-17 Method of making monoacylglyceride oils and food products containing monoacylglyceride oils
EP20706042.7A EP3911164A1 (fr) 2019-01-18 2020-01-17 Procédé de fabrication d'huiles de monoacylglycéride et produits alimentaires contenant des huiles de monoacylglycéride
CN202080018774.0A CN113747796A (zh) 2019-01-18 2020-01-17 制作单酰基甘油酯油的方法和含有单酰基甘油酯油的食物产品

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201962794412P 2019-01-18 2019-01-18
US62/794,412 2019-01-18
US201962833558P 2019-04-12 2019-04-12
US62/833,558 2019-04-12

Publications (2)

Publication Number Publication Date
WO2020150661A1 WO2020150661A1 (fr) 2020-07-23
WO2020150661A9 true WO2020150661A9 (fr) 2021-04-22

Family

ID=69630621

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2020/014182 WO2020150661A1 (fr) 2019-01-18 2020-01-17 Procédé de fabrication d'huiles de monoacylglycéride et produits alimentaires contenant des huiles de monoacylglycéride

Country Status (6)

Country Link
EP (1) EP3911164A1 (fr)
JP (1) JP2022517271A (fr)
CN (1) CN113747796A (fr)
AU (1) AU2020207945A1 (fr)
CA (1) CA3127093A1 (fr)
WO (1) WO2020150661A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020254506A1 (fr) * 2019-06-18 2020-12-24 Palsgaard A/S Procédé de production d'une composition de monoglycéride faible en glycidol et composition de monoglycéride faible en glycidol
JP2024515611A (ja) * 2021-04-13 2024-04-10 グリコスバイオ インコーポレーテッド モノアシルグリセロール及び遊離脂肪酸系組成物による薬物送達

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4391673B2 (ja) * 2000-08-08 2009-12-24 花王株式会社 油脂組成物
US20040209953A1 (en) * 2002-12-06 2004-10-21 Wai Lee Theresa Siu-Ling Glyceride compositions and methods of making and using same
EP2287325A4 (fr) * 2008-05-29 2013-10-02 Kao Corp Procédé de fabrication de matière grasse ou d'huile contenant une grande quantité de diacylglycérol
US9458411B2 (en) * 2010-11-23 2016-10-04 Cargill, Incorporated Lipid-based wax compositions substantially free of fat bloom and methods of making
DK2809789T3 (da) * 2012-01-30 2019-01-02 Arvind Mallinath Lali Enzymatisk fremgangsmåde til fedthydrolyse i et polært organisk opløsningsmiddel
CA3060716A1 (fr) * 2017-05-08 2018-11-15 Bunge Loders Croklaan B.V. Composition d'emulsifiant pouvant etre obtenue a partir d'acides gras libres
CA3078831A1 (fr) * 2017-10-13 2019-04-18 Glycosbio Food Sciences, Inc. Procede de fabrication d'huiles a base de monoacylglycerides et produits alimentaires contenant des huiles a base de monoacylglycerides

Also Published As

Publication number Publication date
CA3127093A1 (fr) 2020-07-23
AU2020207945A1 (en) 2021-07-29
JP2022517271A (ja) 2022-03-07
WO2020150661A1 (fr) 2020-07-23
EP3911164A1 (fr) 2021-11-24
CN113747796A (zh) 2021-12-03

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