EP3911164A1 - Method of making monoacylglyceride oils and food products containing monoacylglyceride oils - Google Patents
Method of making monoacylglyceride oils and food products containing monoacylglyceride oilsInfo
- Publication number
- EP3911164A1 EP3911164A1 EP20706042.7A EP20706042A EP3911164A1 EP 3911164 A1 EP3911164 A1 EP 3911164A1 EP 20706042 A EP20706042 A EP 20706042A EP 3911164 A1 EP3911164 A1 EP 3911164A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- processed oil
- processed
- weight
- acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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Classifications
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
- EPI Exocrine Pancreatic Insufficiency
- PERT Pancreatic Enzyme Replacement Therapy
- Lipids are energy-dense compounds that are the source of essential long chain fatty acids. Consumed lipids, typically comprising a high percentage of triacylglyceride (TAG) are digested with lipases secreted from the pancreas into free fatty acids (FFA) and monoacylglyceride (MAG). Blockage of lipase release from the pancreas results in very poor digestion of triacylglyceride-containing fats and oils. For patients suffering from EPI, this can lead to significant malnutrition because the calories, essential fatty acids and fat-soluble nutrients are trapped in the un-digested lipid particles and pass through the system.
- TAG triacylglyceride
- FFA free fatty acids
- MAG monoacylglyceride
- MAG oil-based products have been evaluated in the clinic as capsule-based nutritional supplements; however, capsules were utilized to avoid the bad taste.
- the starting oil is treated chemically or enzymatically to make MAGs, which are then extracted with solvents and distilled to fractionate the MAGs away from other components of the starting oils.
- These MAG products are sold as relatively pure products containing only negligible amounts of contaminating free fatty acid (FFA), (diacylglycerides) DAGs and TAGs, and with virtually no other compounds.
- FFA free fatty acid
- DAGs diacylglycerides
- lipids into liquid (shakes) and solid (bar) forms that are suitable for“PERT -free” use.
- These formulations can be a source of“Complete Nutrition”, suppling all the caloric and essential fatty acid requirements of individuals.
- Liquid nutrition can be in the form of oral nutritional supplements (ONS) products of products for enteral feeding.
- ONS oral nutritional supplements
- EMO enzyme-modified oil
- MCPD Monochloropropandiol
- glycidyl esters are formed during the refining of edible oils. These compounds are toxic to humans and need to be minimized in food products.
- 3 -MCPD is currently classified as a possible human carcinogen (group 2B) according to The Interational Agency for Research on Cancer (IARC). Glycidol is categorized as probably carcinogenic for humans (group 2A) by IARC and the US National Toxicology program. Current standards recommend exposure of less than 2 ug/kg body weight per day, which is less than 140 ug per day for a 70 kg man, and only 10 ug/day for a 5 kg ( ⁇ 10 lb) baby.
- IARC The Interational Agency for Research on Cancer
- MCPD compounds were first detected in acid (HC1) hydrolyzed protein, but in 2008 the presence ofMCPD esters in refined vegetable oils was discovered. It turned out the problem was widespread. Many edible oils are processed to remove components that negatively impact appearance, taste, shelf stability, safety and consumer acceptance. Mono- and di-acyl glycerols (MAGs and DAGs) in the oils can react with chlorine ions in the deodorization process to produce 3 -Monochloropropanediol (3-MCPD) esters and glycidyl esters (GEs).
- MAGs and DAGs Mono- and di-acyl glycerols
- MAGs and DAGs Mono- and di-acyl glycerols
- GEs glycidyl esters
- Table 1 below shows the levels ofMCPD compounds in a sampling of edible oils in the United States (from Food Additives & Contaminants: Part A, 2013 Vol. 30, No. 12, 2081- 2092).
- Triolein is a TAG that is very rich in oleic acid, as illustrated below. Triolein is 100% oleic acid esterified to glycerol at all three positions. The three positions are defined as“sn-1, sn-2 and sn-3”. Sn is“stereo number.”
- compositions and methods that can provide the health benefits of these oils for individuals suffering from EPI, and to enhance and make the beneficial components of the oils more available.
- the present disclosure is directed to a product comprising a processed oil derived from an oil source.
- the processed oil comprises a MAG content equal to or greater than 30% by weight of the total weight of the processed oil, a DAG content of from about 10% to about 30% by weight of the total weight of the processed oil, and a FFA content of from about 5% to about 60% by weight of the total weight of the processed oil, wherein the processed oil is either free of TAGs or comprises a TAG content that is equal to or less than 5% by weight of the total weight of the processed oil, and wherein 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 oil source is from an origin selected from a plant, an animal, a fish, or mixtures thereof.
- the oil source comprises MCPD compounds.
- the processed oil is substantially free of MCPD compounds.
- non-oil ingredients of said product are selected from antioxidants, vitamins, and mixtures thereof.
- said product comprises greater than 1% by weight MAGs out of the total weight of the product.
- said product comprises greater than 50% by weight MAGs out of the total weight of the product.
- the present disclosure is also directed to a food product.
- the food product comprises an oil and having a caloric density of from about 1 kcal/gram to about 5 kcal/gram, wherein from about 20% to about 50% of calories are derived from said oil.
- the oil of said food product is a processed oil derived from an oil source, wherein the processed oil comprises a MAG content equal to or greater than 30% by weight of the total weight of the processed oil, , a DAG content of from about 10% to about 30% by weight of the total weight of the processed oil, and a FFA content of from about 5% to about 60% by weight of the total weight of the processed oil wherein the processed oil is either free of TAGs or comprises a TAG content that is equal to or less than about 5% by weight of the total weight of the processed oil, and wherein 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 oil source of said food product is from an origin selected from a plant, an animal, or a fish.
- the non-oil ingredients of said food product are selected from antioxidants, vitamins, and mixtures thereof.
- said food product comprises greater than 1% by weight MAGs out of the total weight of the product.
- said food product comprises greater than 50% by weight MAGs out of the total weight of the product.
- said food product has a total weight from about 25 grams to about 3000 grams.
- said food product has a total calorie content from about 1 kcals to about 5 kcals per gram.
- said food product may further comprise a carbohydrate source.
- said food product may further comprise a protein source.
- said oil contributes from 5% to 95% of the total calorie content of the food product.
- the present disclosure is also directed to a method for making a monoacylglycerol- enriched oil.
- the method comprises mixing a starting oil comprising triacylglycerols (TAGs), a buffer solution and a first enzyme capable of hydrolyzing said TAGs to free fatty acids (FFAs) to yield a first reaction mixture; allowing said reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs for a first period of time to yield an aqueous phase and lipid (Free Fatty Acid) reaction product; inactivating said first enzyme in said reaction product; collecting said lipid reaction product; mixing said lipid reaction product and food-grade glycerol and a second enzyme capable of esterifying FFAs to form a second reaction mixture; allowing said second reaction mixture to react for a second period of time to yield a reaction product lipid oil phase and a glycerol phase; inactivating said second enzyme in said reaction product; adding salt to the reaction and separating the lipid oil phase
- TAGs
- said first enzyme is lipase AY.
- said first period of time is a period of time sufficient to hydrolyze at least 94% of the TAGs in said starting oil.
- said first period of time is between about 14 hours and 24 hours.
- said step of allowing said reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs is performed at a temperature between about 30°C and about 35°C.
- 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 second enzyme is lipase G.
- said second period of time is a period of time sufficient to result in enrichment of MAGs in the lipid oil phase of about 60% to 95%.
- said second period of time is between about 24 hours and about 72 hours.
- said step of allowing said second reaction mixture to react for a second period of time to yield a lipid oil phase and a glycerol phase is performed at a
- the method further comprises drying said reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of water from the reaction product.
- said step of drying said reaction product is performed at a temperature between 20°C-30°C.
- said drying step is applied throughout the second period of time.
- said step of inactivating said second enzyme is performed by heating said reaction product.
- said heating is performed at a temperature of at least 70°C for at least 1 hour.
- said step of separating said lipid oil phase from said glycerol phase comprise adding sodium chloride to said reaction product.
- the final concentration of sodium chloride comprises up to 0.3 weight percent sodium chloride.
- the method further comprises before mixing said lipid reaction product and food-grade glycerol and a second enzyme capable of esterifying FFAs and glycerol, re-establishing a nitrogen atmosphere over said lipid reaction product.
- said steps of removing at least a portion of said aqueous phase and replacing said at least a portion of said aqueous phase with about an equivalent volume of water and waiting a second period of time are repeated before performing said step of collecting said lipid reaction product.
- the method further comprises adding tocopherol to said lipid oil phase after collecting said lipid oil phase.
- 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 processed oil comprises oleic acid and linoleic acid in a ratio of between about 0.01 and about 5, the processed oil having greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- a processed oil comprises oleic acid and linolenic acid in a ratio between about 1 and about 100, the processed oil having greater than 50% by weight
- MAGs monoacylglyceride
- a processed oil comprises oleic acid and linoleic acid and has a total fatty acid content, wherein the linoleic acid is present in an amount from about 10% to about 90% by weight out of the total fatty acid content of the processed oil.
- a processed oil has a fatty acid profile substantially the same as the fatty acid profile of 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 linolenic acid is within about 10% 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 linolenic acid 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 method for promoting glucose homeostasis 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.
- a method for treating type P 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.
- a method for promoting glucose homeostasis in a subject in need thereof includes the step of administering to the subject a composition comprising a processed oil of the present disclosure.
- a method for treating diabetes in a subject in need thereof includes the step of administering to the subject a composition comprising a processed oil of the present disclosure.
- FIGURE 1 depicts the TLC separation of components of starting vegetable oil, intermediate FFAs, and final MAG oil.
- FIGURE 2 depicts the TLC separation of components of starting vegetable oil, intermediate FFAs, and final MAG oil.
- FIGURE 3 depicts the distribution of FFA, MAG, DAG, and TAG in“Ensure Original Nutritional Shake” and Enzyme Modified Oil product of the present disclosure (“GBFS”).
- FIGURE 4 depicts a block flow diagram of the process of manufacturing enzyme modified oil.
- FIGURE 5 depicts the distribution of amino acids and peptides in ready-to-drink nutritional drinks and GBFS hydrolyzed pea protein.
- FIGURE 6A depicts the NMR spectrum of authentic TAG (tristerin).
- FIGURE 6B depicts the NMR spectrum for enzyme modified oil produced from almond oil.
- FIGURE 7 depicts the increase in serum triglycerides following ingestion of the EMO- based ready-to-drink shake.
- FIGURE 8 depicts the increase in serum triglycerides following ingestion of MAG-based RTDS without PERT.
- FIGURE 9 depicts the serum glucose levels for patients (averaged) following ingestion of MAG-based RTDS without PERT or a standard nutritional supplement with PERT.
- FIGURE 10 depicts the serum triglyceride levels for patients (averaged) following ingestion of-based RTDS without PERT or a standard nutritional supplement with PERT.
- FIGURE 11 depicts the percentage of certain fatty acids in the canola oil and canola EMO of Example 13 and two commercial monoglyceride samples.
- FIGURE 12A depicts the amount of various compounds in the canola oil and canola EMO of Example 14 based on LC/MS/MS analysis.
- FIGURE 12B depicts the amount of various compounds in the canola oil and canola EMO of Example 14 based on LC/MS/MS analysis.
- a MAG-enriched oil is an oil having a MAG content that is greater than the starting MAG content prior to the enrichment process or that the starting oil has a greater percentage of MAG than the oil possessed prior to the enrichment process.
- the enrichment process can be by conversion of TAGs to MAGs thereby increasing the MAG content and percentage and decreasing the TAG content or percentage.
- a triacylglycerol also known as a triglyceride, is a glyceride consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. TAGs may also be classified as having a long or medium chain length. Long chain TAGs contain fatty acids with 14 or more carbons, while medium chain TAGs contain fatty acids with 6 to 12 carbons. Long chain TAGs can include omega-3 and omega-6 fatty acids. Medium chain TAGs have saturated fatty acids and thus do not contain omega-3 or omega-6 fatty acids. Long chain TAGs (LCT) and medium chain triglycerides (MCT) can serve as energy sources.
- TAGs long chain TAGs
- MCT medium chain triglycerides
- a diacylglycerol also known as a diglyceride, is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
- a monoacylglycerol also known as a monoglyceride, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage
- processed oil refers to a non-naturally occurring oil composition substantially free TAGs or having a reduced amount of TAGs with respect to the pre-modified or pre-processed oil.
- the terms“enzyme-modified oil” or“EMO” refers to a processed oil wherein TAGs were enzymatically converted to MAGs, such as, for example, using the enzymatic conversion of the present disclosure.
- the term“food product” refers to a manufactured or non-naturally occurring food product. It should be understood that the food product referred to herein, while manufactured and non-naturally occurring as a whole, can comprise various combinations of natural ingredients where said combinations either do not occur in nature or where said combinations do exist in nature, they do not exist in the relative amounts used in the food product.
- the terms“patient,”“individual,” and“subject” are used interchangeably herein, and refer to a mammalian subject to be treated, with human patients being preferred. In some cases, the methods of the invention find use in experimental animals, in veterinary application, and in the development of animal models for disease, including, but not limited to, rodents including mice, rats, and hamsters, and primates.
- “Treatment” is an intervention performed with the intention of preventing the development or altering the pathology or symptoms of a disorder. Accordingly,“treatment” can refer to both therapeutic treatment and prophylactic or preventative measures. Those in need of treatment include those already with the disorder as well as those in which the disorder is to be prevented. In tumor (e.g., cancer) treatment, a therapeutic agent may directly decrease the pathology of tumor cells, or render the tumor cells more susceptible to treatment by other therapeutic agents, e.g., radiation and/or chemotherapy.
- tumor e.g., cancer
- a“non-oil ingredient” is an ingredient that is naturally present in an oil source that is not a MAG, DAG, TAG, FFA or lipid.
- the starting oils may comprise, by way of example but not limitation, oils derived from plants such as olive oil, almond oil, canola oil, coconut oil, cottonseed oil, palm kernel oil, palm olein oil, palm stearin oil, peanut oil flaxseed oil, sunflower seed oil, com oil, grapeseed oil, palm oil, soybean oil, or oil derived from animals such as fish oil, sardine oil, or anchovy oil, or algal oil, or mixtures of any of the foregoing plant oils and/or animal oils.
- oils derived from plants such as olive oil, almond oil, canola oil, coconut oil, cottonseed oil, palm kernel oil, palm olein oil, palm stearin oil, peanut oil flaxseed oil, sunflower seed oil, com oil, grapeseed oil, palm oil, soybean oil, or oil derived from animals such as fish oil, sardine oil, or anchovy oil, or algal oil, or mixtures of any of the foregoing plant oils and/or animal oils.
- the starting oil comprises a blend of olive oil, sunflower seed oil, and flaxseed oil, wherein the from about 50% to about 80% by weight of the total weight of the starting oil is olive oil, from about 10% to about 30% by weight of the total weight of the starting oil is suflower seed oil, and from about 5% to about 20% by weight of the total weight of the starting oil is flaxseed oil.
- from about 50% to about 80% by weight of the total weight of the starting oil is olive oil, from about 10% to about 30% by weight of the total weight of the starting oil is flax seed oil, and from about 5% to about 20% by weight of the total weight of the starting oil is sunflower seed oil.
- the starting oils comprise MCPD compounds.
- the MCPD compounds may be in an amount from about 0.30 mg/kg to about 12.0 mg/kg, or from about 1.0 mg/kg to about 11.00 mg/kg, or from about 2.00 mg/kg to about 10.50 mg/kg.
- starting oils comprising MCPD compounds includes almond, canola, coconut, com, cottonseed, grape seed, olive, palm, palm kernel, palm olein, palm stearin, peanut, soybean, and sunflower.
- the process of making a product enriched in MAGs comprises a first step of hydrolyzing TAGs.
- the hydrolysis of TAGs may be carried out by a lipase such as lipase AY (Amano Enzymes, USA Elgin IL, USA), or any non-regiospecific lipase that cuts at the sn-1, sn-2 and sn-3 positions.
- the first step of hydrolyzing TAGs may be carried out at a temperature of about 30°C to 35°C.
- the first step of hydrolyzing TAGs may be carried out at a temperature of 30°C to 35°C, 31°C to 35°C, 32°C to 35°C, 33°C to 35°C, 34°C to 35°C, 30°C to 34°C, 31°C to 34°C, 32°C to 34°C, 33°C to 34°C, 30°C to 33°C, 31°C to 33°C, 32°C to 33°C, 30°C to 32°C, 31°C to 32°C, 30°C to 31°C, or 30°C, 31°C, 32°C, 33°C, 34°C, or 35°C.
- the first step of hydrolyzing TAGs may be carried out for about 14 hours to 24 hours.
- the first step of hydrolyzing TAGs may be carried out for 14 hours to 20 hours, 14 hours to 16 hours, 18 hours to 24 hours, 22 hours to 24 hours, 18 hours to 20 hours, or about 14 hours, 15 hours, 16 hours, 17 hours, 18 hours, 19 hours, 20 hours, 21 hours, 22 hours, 23 hours, or 24 hours.
- the first step of hydrolyzing TAGs results in hydrolysis of substantially all TAG.
- the first step of hydrolyzing TAGs results in hydrolysis of 94% to 100%, 95% to 100%, 96% to 100%, 97% to 100%, 98% to 100%, 99% to 100%, 94% to 99%, 95% to 99%, 96% to 99%, 97% to 99%, 98% to 99%, 94% to 98%, 95% to 98%, 96% to 98%, 97% to 98%, 94% to 97%, 95% to 97%, 96% to 97%, 94% to 96%, 95% to 96%, or 94% to 95% TAG, or at least 94%, 95%, 96%, 97%, 98%, 99%, or 100% of TAG.
- the process of making a product enriched in MAGs comprises a second step of esterification with glycerol to enrich MAG oil content.
- this second step of esterification may be carried out by a lipase such as lipase G, (Amano Enzymes, USA Elgin IL, USA), or any regiospecific lipase that catalyzes esterification at the sn-1 position but does not effectively catalyze formation of the second or third ester on glycerol (to make DAGs and TAGs).
- the second step of esterification with glycerol to enrich MAG oil content results in enrichment of MAGs in the product by about 70% to 95%.
- the MAG oil content may be enriched by 70% to 95%, 75% to 95%, 80% to 95%, 85% to 95%, 90% to 95%, 70% to 90%, 75% to 90%, 80% to 90%, 85% to 90%, 70% to 85%, 75% to 85%, 80% to 85%, 70% to 80%, 75% to 80%, 70% to 75%, or 70%, 75%, 80%, 85%, 90%, or 95%.
- the second step of esterification with glycerol may be carried out at a temperature of about 17°C to 23 °C.
- the esterification with glycerol may be carried out at a temperature of 17°C to 23°C, 18°C to 23°C, 19°C to 23°C, 20°C to 23°C, 21°C to 23°C, 22°C to 23°C, 17°C to 22°C, 18°C to 22°C, 19°C to 22°C, 20°C to 22°C, 21°C to 22°C, 17°C to 21°C, 18°C to 21°C, 19°C to 21°C, 20°C to 21°C, 17°C to 20°C, 18°C to 20°C, 19°C to 20°C, 17°C to 19°C, 18°C to 19°C, 17°C to 18°C, or 17°C, 18°C, 19°C, 20°C, 21°C,
- the second step of esterification with glycerol may be carried out for about 24 hours to 72 hours.
- the second step of esterification with glycerol may be carried out for 24 hours to 72 hours, 36 hours to 72 hours, 48 hours to 72 hours, 60 hours to 72 hours, 24 hours to 60 hours, 36 hours to 60 hours, 48 hours to 60 hours, 24 hours to 48 hours, 36 hours to 48 hours, 24 hours to 36 hours, or 24 hours, 30 hours, 36 hours, 42 hours, 48 hours, 54 hours, 60 hours, 66 hours, or 72 hours.
- the process of making a product enriched in MAGs comprises a third step of lipase inactivation and phase separation.
- the resulting product from the above embodiments results in a processed oil having a MAG content of equal to or greater than 40% by weight based on the total weight of the processed oil.
- the MAG content is from about 40% to about 99% by weight based on the total weight of the processed oil.
- the MAG content is from about 50% to about 99% by weight based on the total weight of the processed oil.
- the MAG content is from about 60% to about 99% by weight based on the total weight of the processed oil.
- the MAG content is from about 70% to about 99% by weight based on the total weight of the processed oil. In certain aspects, the MAG content is from about 80% to about 99% by weight based on the total weight of the processed oil. In certain aspects, the MAG content is from about 50% to about 80% by weight based on the total weight of the processed oil. In any of the above aspects, the TAG content is equal to or less than 5% by weight based on the total weight of the processed oil. In any of the above aspects, the TAG content is equal to or less than 4%, equal to or less than 3%, equal to or less than 2%, equal to or less than 1% by weight based on the total weight of the processed oil.
- the resulting product from the above embodiments results in a processed oil that is substantially free of MCPD compounds generally, but also when the starting oils have more than 0.30 mg/kg MCPD compounds and in some instances from about 1.0 mg/kg to about 12.00 mg/kg. More specifically, the processed oil resulting from the above methods comprises less than 100 mg/kg MCPD and even to levels that are not detectable by standard assays.
- the term“substantially free” with respect to the amount of MCPD levels in a processed oil of the present invention means levels that are below the limits of detection for the assay described in Example 11 below.
- the resulting product from the above embodiments results in a processed oil that is enriched in MAGs, specifically 1-MAGs (MAGs esterified at the sn-1 position).
- 1-MAGs MAGs esterified at the sn-1 position
- 1-OG 1-oleyl monoacylglyceride
- the manufacturing process embodiments of the present disclosure can yield three 1-OG molecules from a single triolein molecule, while digestion of triolein by pancreatic lipases can only yield one-third of the total oleic acid in monoacylglycerol form, specifically as 2-monoacylglycerol (2-OG) but not 1-OG, because the lipase liberates the oleic acid moieties at the sn-1 and sn-3 positions as free fatty acids.
- a processed oil produced by the manufacturing methods of the present disclosure can yield up to three times the 1-OG content compared to normal digestion processes.
- the below reaction schematic shows the conversion of triolein to 2-OG and two free oleic acid molecules (process A - normal digestion) and of triolein to 3 molecules of 1-OG by the process of the present disclosure (process B).
- 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 maricmum, 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.
- linoleic (omega-3 fatty acid) and linolenic acid (omega-6 fatty acid) are known to be essential for humans as they can be used in the creation of longer and more desaturated fatty acids otherwise known as long-chain polyunsaturated fatty acids (LC-PUFA), including eicosapentaenoic acid (EPA) and docosahexanenoic acid (DHA).
- LC-PUFA long-chain polyunsaturated fatty acids
- EPA eicosapentaenoic acid
- DHA docosahexanenoic acid
- a product comprises a processed oil of the present disclosure.
- the processed oil is itself a stand-alone product.
- the processed oil comprises a MAG content equal to or greater than 30% by weight of the total weight of the processed oil.
- the processed oil comprises a MAG content of about 30% to 95%, 40% to 95%, 50% to 95%, 60% to 95%, 70% to 95%, 80% to 95%, 90% to 95%, 30% to 90%, 40% to 90%, 50% to 90%, 60% to 90%, 70% to 90%, 80% to 90%, 30% to 80%, 40% to 80%, 50% to 80%, 60% to 80%, 70% to 80%, 30% to 70%, 40% to 70%, 50% to 70%, 60% to 70%, 30% to 60%, 40% to 60%, 50% to 60%, 30% to 50%, 40% to 50%, or about 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% by weight of the total weight of the processed oil.
- the processed oil comprises a DAG 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 10%dress 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.
- 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.
- the processed oil is either free of TAGs or comprises a TAG content that is equal to or less than 5% by weight of the total weight of the processed oil.
- the processed oil comprises a TAG content that is about 0% to 5%, 1% to 5%, 2% to 5%, 3% to 5%, 4% to 5%, 0% to 4%, l% to 4%, 2% to 4%, 3% to 4%, 0% to 3%, 1% to 3%, 2% to 3%, 0% to 2%, l% to 2%, 0% to l%, or 0%, 1%, 2%, 3%, 4% or 5% by weight of the total weight of the processed oil.
- the TAG content can be less than 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.1%.
- the processed oil comprises from about 30% to 80% MAG by weight of the total weight of the processed oil, from about 10% to about 30% DAG by weight of the total weight of the processed oil, from about 0% to about 5% TAG by weight of the total weigh of the processed oil, and from about 5% to about 60% FFA by weight of the total weight of the processed oil.
- 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.
- non-oil ingredients may include antioxidants such as tocopherols, which include alpha-tocopherol, beta-tocopherol, delta- tocopherol, gamma-tocopherol, alpha-tocotrienol, beta-tocotrienol, delta-tocotrienol, or gamma- tocotrienol, and other vitamins such as Vitamin K and structurally similar 2-methyl- 1,4- naphthoquinone (3-) derivatives.
- the antioxidant is selected from natural (e.g., mixed tocopherols or ascorbic acid) and synthetic (e.g, Butyl ated Hydroxy Anisole or Butylated HydroxyToluene) antioxidants.
- non-oil ingredients include ceramide phosphates, monogalactosyl diacyglycerols, phosphatidyl methanol, sitosteryl esters, campesterol esters, sphingolipids, phosphatidyl glycerol, wax esters, and sphingomyelin.
- the processed oil comprises oleic acid monoglyceride (MOG) and has a total fatty acid content.
- the MOG can contribute between about 5% and about 75% by weight of the total fatty acid content of the processed oil. In some embodiments, by way of example, but not limitation, the MOG can contribute between about 10% and about 75%, about 20% and about 75%, about 30% and about 75%, about 40% and about 75%, about 50% and about 75%, or about 60% and about 75% by weight of the total fatty acid content of the processed oil. In some embodiments, the processed oil comprises oleic acid in amount of about 5% and about 75% by weight of the total fatty acid content of the processed oil.
- the oleic acid can contribute between about 10% and about 75%, about 20% and about 75%, about 30% and about 75%, about 40% and about 75%, about 50% and about 75%, or about 60% and about 75% by weight of the total fatty acid content of the processed oil.
- the processed oil comprises MOG and the MOG comprises at least 50% by weight 1-oleyl monoglyceride (1-OG) out of the total amount of MOG.
- the processed oil can comprise at least 50%, at least 60%, at least 70%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 99% 1- OG out of the total amount of MOG.
- the processed oil comprises oleic acid in an amount of about 10% to about 75% by weight out of the total fatty acid content of the processed oil.
- the oleic acid can be present in an amount of about 10% to about 75%, about 20% to about 75%, about 30% to about 75%, about 40% to about 75%, about 50% to about 75%, about 60% to about 75%, about 10% to about 20%, about 10% to about 30%, about 10% to about 40%, about 10% to about 50%, or about 10% to about 60% by weight out of the total fatty acid content of the processed oil.
- the oleic acid is esterified at the sn-1 position.
- the processed oil can comprise at least 50%, at least 60%, at least 70%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 99% of oleic acid esterified at the sn-1 position out of the total amount of oleic acid.
- the processed oil comprises linoleic acid in an amount of about 1.5% to about 90% by weight out of the total fatty acid content of the processed oil.
- the linoleic acid can be present in an amount of about 10% to about 90%, about 20% to about 90%, about 30% to about 90%, about 40% to about 90%, about 50% to about 90%, about 60% to about 90%, about 70% to about 90%, about 80% to about 90%, about 10% to about 25%, about 10% to about 20% by weight out of the total fatty acid content of the processed oil.
- the processed oil comprises oleic acid and linoleic acid with a ratio of oleic acid to linoleic acid between about 0.01 and 5.
- the ratio of oleic acid to linoleic acid can be between about 1 to about 5, about 1 to about 4, about 1 to about 3, about 1 to about 2, about 1.5 to about 5, about 1.5 to about 4, about 1.5 to about 3, about 1.5 to about 2, about 2 to about 5, about 2 to about 4, about 2 to about 3, about 2.5 to about 5, about 2.5 to about 4.5, about 2.5 to about 4, about 2.5 to about 3.5, about 2.5 to about 3, about 3 to about 5, or about 3 to about 4.
- the processed oil comprises linolenic acid in an amount of about 0.01% to about 2% by weight out of the total fatty acid content of the processed oil.
- the linolenic acid can be present in an amount of about 0.1 to about 2%, about 0.5 to about 2%, about 1% to about 2%, or about 1.5% to about 2% by weight out of the total fatty acid content of the processed oil.
- the processed oil comprises oleic acid and linolenic acid with a ratio of oleic acid to linoleic acid of about 1 to about 100.
- the ratio of oleic acid to linolenic acid can be between about 10 and about 100, about 20 and about 100, about 30 and about 100, about 40 and about 100, about 50 and about 100, about 60 and about 100, about 70 to about 100, about 10 to about 90, about 10 to about 80, about 10 to about 70, about 10 to about 60, about 10 to about 50, about 10 to about 40, about 10 to about 30, or about 10 to about 20.
- reference to fatty acids in the claims should not be understood as limited to the free fatty acid only, and can refer to the fatty acid in glyceride form.
- the fatty acid will predominantly be in the MAG form and in the pre- processed oil it will be predominantly in the TAG form. In certain instances, the fatty acid to a lesser extent can be in the free or DAG form. In the processed oil, the free fatty acid will typically be less than 10%.
- the processed oil has a fatty acid profile that is substantially the same as the fatty acid profile of the pre-processed oil from which the processed oil was produced.
- the fatty acid profile of the processed oil can be within about 10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about 3%, about 2%, or about 1% for each component of the fatty acid profile.
- the fatty acid profile comprises oleic acid, linoleic acid and linoleic acid.
- any combination of fatty acids may form the fatty acid profile.
- the fatty acid profile can comprise any combination of fatty acids listed in Table 2 as well as EPA and DHA.
- the processed oil comprises three times the amount of MAG molecules compared to the number of TAG molecules in the pre-processed oil from which the oil was produced.
- the amount oleic acid in the form of MAGs in the processed oil can be up to three times the amount of oleic acid in TAGs in the pre-processed oil.
- the amount of oleic acid in the form of MAG in the processed oil can be 1.1, 1.25, 1.5, 1.75, 2.0, 2.25, 2.5, 2.75 or 3 times the amount of oleic acid in the form of TAGs in the pre-processed oil.
- each oleic acid moiety in the form of TAGs in the pre-processed oil can be converted to an oleic acid MAG, such that up to three oleic acid moieties, as in triolein, would be converted into three oleic acid MAGs.
- the amount of MAGs in the processed oil is three times the amount of TAGs in the pre-processed oil from which the processed oil was produced.
- the number of MAGs produced corresponds to about three times the number of TAGs in the pre-processed oil.
- the processed oil comprises oleic acid in the oleic acid monoglyceride form in an amount that is about the same as the amount of oleic acid in the pre-processed oil from which the processed oil was produced.
- the product or food product can comprise at least 1% MAGs.
- the food product can comprise at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50% or more MAGs by weight of the product or food product and any range or amount therebetween.
- the product or food product can comprise between 5% to 15% weight MAGs by total weight of the product or food product.
- the product or food product can comprise at least 3% of the processed oil of any of the embodiments herein by weight of the total weight of the product or food product.
- the food product can comprise at least 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% or more of the processed oil of any of the embodiments herein by weight of the product or food product and any range or amount therebetween.
- the food product may further comprise a carbohydrate source.
- a carbohydrate source may comprise simple sugars such as glucose and fructose, derived from carbohydrate sources such as fruit and agave syrups.
- carbohydrate sources include other plant-based sugar syrups, starches, and sugar alcohols.
- the food product may further comprise a protein source.
- the protein source can be hydrolyzed or partially hydrolyzed.
- a protein source may comprise dairy protein (casein and whey), and other plant proteins including protein from soy, rice and rice bran, lentils, chickpeas, peanuts, almonds, spirulina (algal), quinoa, mycoprotein, chia seeds and hemp seeds.
- the hydrolyzed protein may be extensively hydrolyzed wherein the pea protein is enriched in peptides of 1 to 10 amino acids in length.
- the protein is enriched in peptides of 1 to 10 amino acids in length by about 25% to 75% compared to commercial partially hydrolyzed protein and other whey-based hydrolysate products such as Peptamen and Crucial.
- the protein is enriched in peptides of 1 to 10 amino acids in length by at least 25% to 75%, 35% to 75%, 45% to 75%, 55% to 75%, 65% to 75%, 25% to 65%, 35% to 65%, 45% to 65%, 55% to 65%, 25% to 55%, 35% to 55%, 45% to 55%, 25% to 45%, 35% to 45%, 25% to 35%, or 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or 75%.
- the food product can be a liquid, semi-solid or solid.
- a semi-solid can include a pudding, mousse, popsicle or ice cream-like product.
- a liquid could be a shake or other beverage.
- a solid could be a bar or other solid food product.
- the product or food product further comprises a viscosity altering agent.
- the viscosity altering agent can be, by way of example but not limitation, xanthan gum or gum acacia.
- the product or food product can further comprises a structure or stability enhancing component such as, by way of example but limitation, gum Arabic, sunflower lecithin and xanthan gum.
- the product or food product further comprises a fiber source, such as, by way of example but limitation, oligosaccharides.
- the product or food product can further comprise a food preservative such as, by way of example, but not limitation sodium benzoate or potassium sorbate.
- a product or food product further comprises a flavor, masker or blocker.
- flavorings can include chocolate, vanilla, strawberry or other flavors.
- the food product has a total weight of at least 25 grams.
- the food product can have a weight of at least 25, 50, 100, 250, 500, 1000, 1500, 2000, 2500, 3000 grams or more. In some embodiments, the food product has a total weight from about 25 grams to about 3000 grams.
- the food product may have a weight from 25 grams to 3000 grams, 25 grams to 2500 grams, 25 grams to 2000 grams, 25 to 1000 grams, 25 grams to 500 grams, 50 grams to 3000 grams, 50 grams to 2500 grams, 50 grams to 2000 grams, 50 grams to 1500 grams, 50 grams to 1000 grams, 50 grams to 500 grams, 100 grams to 3000 grams, 100 grams to 2500 grams, 100 grams to 2000 grams, 100 grams to 1500 grams, 100 grams to 1000 grams, 100 grams to 500 grams, 250 grams to 3000 grams, 250 grams to 2500 grams, 250 grams to 2000 grams, 250 grams to 1500 grams, 250 grams to 1000 grams, 250 grams to 500 grams, 500 grams to 3000 grams, 500 grams to 2500 grams, 500 grams to 2000 grams, 500 grams to 1500 grams, 500 grams to 1000 grams, 1000 grams to 3000 grams, 1000 grams to 2500 grams, 1000 grams to 2000 grams, 1000 grams to 1500 grams, 1500 grams to 3000 grams, 2000 grams to 3000 grams, 2000 grams to 2500 grams, 25 grams to 250 grams, 50 grams to 3000 grams, 50 grams to 2500 grams, 50
- the food product has a total calorie content from about 200 kcals to 1000 kcals.
- the food product may have a calorie content from about 200 kcals to 1000 kcals, 400 kcals to 1000 kcals, 600 kcals to 1000 kcals,
- about 20% to 75% of calories in the food product are derived from an oil or fat.
- the oil or fat is the processed oil of any of the embodiments herein.
- the processed oil has a MAG content of equal to or greater than 30% by weight of the total weight of the processed oil.
- the processed oil has a MAG content of from about 40% to about 99% by weight of the total weight of the processed oil.
- the processed oil has a TAG content of less than 5% by weight of the total weight of the processed oil.
- about 20% to 50% of calories in the food product are derived from the carbohydrate source.
- 10% to 50% of calories in the food product are derived from the protein source.
- a food product of the present disclosure comprises a processed oil of the present disclosure.
- the EMO-based products are consumed by individuals with poorly functioning digestive systems, by way of example but not limitation, individuals suffering from EPI or individuals who take PERT with food. In some embodiments, the EMO- based products are consumed by individuals who desire faster or more complete conversion of lipids to serum triglycerides.
- a method for feeding a human or animal subject with a poorly functioning digestive system comprises administering to said patient a food product described in any of the above embodiments or combinations of such embodiments.
- the human or animal subject is suffering from EPI.
- the human or animal subject is suffering from cystic fibrosis, pancreatitis, pancreatic cancer, or cholestasis.
- a method for promoting glucose homeostasis in a subject in need thereof comprising administering to the subject a composition comprising a processed oil of the present disclosure.
- the subject is suffering from a condition that affects glucose homeostasis.
- the condition is insulin resistance or diabetes mellitus.
- the condition is type P diabetes.
- the diabetes is type P diabetes.
- 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
- DI deionized
- Reactor temperature was increased to 70° C and agitation resumed for 1 hour to inactivate the enzyme.
- Step 2 Esterification with Glycerol.
- FFA re-esterified with glycerol they produce a mixture of MAGs, DAGs and TAGs.
- the proportion of MAGs in the product can be highly enriched (at least 60% but as high as 95%). This was un-expected.
- the reaction product from step 1 (about 10L) was cooled to about 30° C and agitated at 300 RPM. 10 kg of Food-grade glycerol were added to the Lipid mixture, and the temperature maintained at ⁇ 30° C. The mixture was agitated to generate a dispersion of the oil and glycerol.
- a vacuum was applied: First a vacuum (25 mmHg, Torr) was applied with receiver in place to collect water. Once evaporation of the residual water had stopped, 20g of Amano Lipase G dissolved in water (50 mL) was added to the reactor.
- the temperature was lowered to 23 °C and the vacuum was changed to 5 mmHg using an oil diaphragm pump and a cold trap to collect the water.
- the mixture was stirred at 300 RPM at 23 °C under vacuum for 72 hrs, at which time the vacuum was broken and the mixture was blanketed with nitrogen gas.
- the mixture was analyzed after 72 hrs with TLC to evaluate the conversion to MAGs as shown in FIGURE 1.
- Step 3 Lipase Inactivation and Phase Separation. After the reaction was complete, the lipase was inactivated by heating the mixture (under a Nitrogen gas blanket) to 70°C for 1 hr. At this point the MAG oil and glycerol are well mixed and very hard to separate through traditional gravity or centrifugal methods. After considerable experimentation, we found that the lipid can be separated from the excess glycerol by adding 0.3%wt of salt (NaCl) to the reaction mixture under agitation. The product mixture was then allowed to cool to about 60°C and left without agitation for about 1 hr.
- salt NaCl
- the lipid oil phase separated from the remaining heavier glycerol phase.
- the glycerol phase was removed: it contains some salt, residual water and the dissolved inactivated enzyme which is contained in the visible interface.
- the glycerol phase can be reused after membrane filtration and should be kept for recycle.
- Tocopherol (Vitamin E) was added to give a concentration of 200 ppm (0.02% wt) of the product oil.
- the hydrolyzed oil about 10 kg was ready for use and could be stored under nitrogen blanket).
- Example 2 Characterization of oil produced in Example 1.
- FIGURE 1 depicts the final results of steps 1 to 3 in the process of making a product enriched in MAG compared to starting TAG-rich oil as describe in Example 1.
- FIGURE 2 illustrates that tocopherol initially present in the olive oil is preserved following the steps described in Example 1.
- the tocopherol spot can be seen tracking above the TAG spot in all three lanes.
- a sample 500 ml was added to a 5-ml reaction tube containing 2 ml boron trifluoride solution (12% in methanol), 20 ml dimethoxypropane and 100 m ⁇ of a tridecanoic acid internal standard solution (10 mg/ml).
- the reaction tube was vortexed and incubated in a heating block at 60°C for 30 minutes.
- the reaction tube was removed from the heating block and allowed to cool for 15 minutes. Then, 1 ml of distilled water was added to quench the reaction, followed by 1 ml of hexane. The reaction tube was vortexed for 60 seconds and the phases were allowed to separate for 3 minutes. The top (hydrophobic) phase was removed to a 1.5-ml tube containing about 50 mg sodium sulfate (anhydrous). After vortexing for 60 seconds, the 1.5-ml tube was centrifuged and -500 m ⁇ of the clarified, dried hydrophobic phase was transferred to a gas chromatography sample vial.
- FIGURE 3 depicts the distribution of FFA, MAG, DAG, and TAG in Ensure and a GBFS product of the present disclosure. Percent FFA, MAG, DAG and TAG in the oils determined by Thin Layer Chromatography.
- Example 3 Another example of the process of making a product enriched in MAG compared to starting TAG-rich oil.
- Plant oil was added to citric acid and sodium hydroxide (caustic) in DI water and heated to 33 °C +/- 2 °C. A low vacuum was applied to de-gas to remove oxygen. Lipase AY was added. Hydrolysis of the mixture was performed for 14 - 24 hours under a Nitrogen blanket at a temperature of 33 °C +/- 2 °C.
- Lipase was inactivated at a temperature of 70 °C +/- 2 °C for 1 hour. The aqueous phase with inactivated enzyme was drained. Glycerol was added. Then the reaction was cooled to 22 °C +/- 2 °C. Then Lipase G was added and water was evaporated under a moderate vacuum.
- Re-esterification was carried out for 72 hours under high vacuum (around 720 mmHg) at a temperature of 20 °C +/- 2 °C.
- Lipase G was inactivated at 70 °C +/- 2 °C for one hour and salt was added to the reaction.
- Enzyme inactivation and phase separation was carried out under a Nitrogen blanket for 1 hour at 70 °C +/- 2 °C.
- the aqueous phase with inactivated enzyme, glycerol, and salt was drained.
- the reaction was cooled to 60 °C +/- 2 °C.
- Antioxidant was added.
- the final product was stored at 4 °C +/- 2 °C under nitrogen.
- Example 4 Ready-to-Drink formulation incorporating MAGs and hydrolyzed protein
- a product of the present disclosure was produced as a conventional“milk shake” formulation that includes a source of fats, proteins, carbohydrates, vitamins and fiber in addition to the traditional surfactants and stabilizing agents typically found in these products.
- An individual serving was 250 ml.
- ingredients as would appear on the ingredient label were as follows: Water, Organic Agave Syrup, Hydrolyzed Pea Protein, Hydrolyzed Oil Blend, Gum Arabic, Sunflower Lecithin, Xanthan Gum, Oligosaccharides, Potassium Sorbate, Sodium Benzoate, Instant Coffee, Natural Organic Vanilla Flavor, Vitamin C, Vitamin E Succinate, Vitamin A Palmitate, Niacinamide, D-Calcium Pantothinate, Pyrodoxine HC1, Thiamine HC1, Riboflavin, Vitamin D3, Folic Acid, Cyanocobalamin, Vitamin K2.
- Carbohydrates were supplied as simple sugars (glucose and fructose) from fruit and agave syrups.
- Protein in the product was partially hydrolyzed pea protein (PURIS Pea Protein 870H, World Food Processing LLC, Turtle Lake, WI 54889).
- EHP extensively hydrolyzed pea protein
- peptides in a size range more bio-available for transport across the intestinal wall.
- EHP was produced by further enzyme hydrolysis.
- partially hydrolyzed pea protein (Puris Pea Protein 870H described above) protein was dissolved in 100 mM Phosphate buffer to a concentration of 25 mg/ml. Enzyme was added and the reaction incubated at 50° overnight.
- Three different commercial GRAS enzymes were evaluated: Alcalase, Thermoase and flavourzyme.
- the average size of un-hydrolyzed pea protein was -200 amino acids.
- the average size of the Puris Pea 870H partially hydrolyzed material was 34 amino acids, with a substantial amount in the 2-40 amino acid range, similar to other (whey-based) protein hydrolysate products.
- FIGURE 5 depicts the distribution of amino acids and peptides in ready-to-drink nutritional drinks as reported in E. Phillips et al., 2005 Peptide-Based Formulas: the
- FIGURE 5 depicts the percentage of amino acids (Y - Axis) of the size 1 amino acid, 2-4 amino acids, 9-10 amino acids, 10-40 amino acids, or greater than 40 amino acids in the products Peptamen, Perative, Crucial, Pivot, and the GBFS of the present disclosure (X-Axis).
- the average size of the GBFS EHP is 3-4 amino acids, mostly 1 - 7 amino acids.
- Fat is provided in the form of the re-structured Lipid MAG and were produced from a blend of olive oil (70%), sunflower oil (21%) and flax seed oil (9%) to provide the energy and other benefits of poly-unsaturated fatty acids (PUFA), omega-6 PUFA and omega-3 PUFA.
- PUFA poly-unsaturated fatty acids
- omega-6 PUFA omega-6 PUFA
- omega-3 PUFA Omega-6/omega-3 ratio
- Gum Arabic, sunflower lecithin, and xanthan gum are common GRAS food ingredients used to provides structure and stability for the drink. Oligosaccharides provide non- digestable fiber. Potassium Sorbate and Sodium Benzoate are common food preservatives.
- % DV Percentage Daily Values
- Table 4 depicts a scan of TLC plates illustrating the concentrations of MAG and FFA in the enzyme modified EMO produced from an olive oil/flax oil/sunflower oil blend (ratio of 7/2/1).
- step 2 was extended to 84 hours to establish upper limits on timing and temperature to avoid TAG formation.
- reaction time of 72 hours for step 2 was found to be a practical and productive stopping point and illustrated in Example 6.
- TAG-free EMO was produced using almond oil. Reaction conditions were as described in Example 1. Step 2 was 72 hours to minimize TAG production.
- FIGURES 6A-6B depict the 13 C-NMR analysis of the EMO produced from almond oil.
- FIGURE 6A illustrates that 13 C-NMR signal associated with authentic TAG
- FIGURE 6B illustrates the 13 C-NMR signal for the EMO. It shows that there is no discemable TAG signals. Integration of the actual signals indicates an acyl glycerol distribution between MAG:DAG of 88%: 12%. Samples were analyzed on a JEOL model ECA600II NMR spectrometer operating at 600 MHz proton and 150 MHz carbon. Samples were made up in 5 mm tubes and run locked with CDC13 at ambient temperature.
- Example 7 Clinical Testing of an EMO -based Ready-To-Dr ink-Shake
- the clinical study was a single center, randomized, double-blind, cross-over trial assessing an EMO-based ready-to-drink shake (RTDS) for blood lipid levels, safety, tolerability and palatability compared to a standard nutritional supplement used concomitantly with pancreatic enzyme replacement therapy capsules (“PERT”).
- RTDS EMO-based ready-to-drink shake
- pancreatic enzyme product 5. Currently receiving treatment with a commercially available pancreatic enzyme product for more than 3 months.
- Stable body weight defined as no more than 5% decline within 3 months of enrollment.
- Medically acceptable methods of birth control include bilateral tubal ligation or the use of either a contraceptive implant, a contraceptive injection (Depo-ProveraTM), an intrauterine device, or an oral contraceptive taken within the past 3 months where the subject agrees to continue using during the study or to adopt another birth control method, or a double-barrier method which consists of a combination of any two of the following: diaphragm, cervical cap, condom, or spermicide.
- DIOS distal intestinal obstruction syndrome
- pancreatin capsules Any type of malignancy involving the digestive tract in the last 5 years. 12. Known allergy to pancreatin or inactive ingredients (excipients) of pancreatin capsules.
- lipid lowering therapy including statins, fibrates, niacin, and proprotein convertase subtilisin kexin type 9 (PCSK9) inhibitors that cannot be held at least 14 days prior to Day 1 and through Day 15 of the study .
- PCSK9 proprotein convertase subtilisin kexin type 9
- Patients were male or female, aged 12 years or older with a diagnosis of cystic fibrosis. Patients were also currently receiving treatment with a commercially available pancreatic enzyme product for more than 3 months and had a clinically stable condition without evidence of acute respiratory disease within 1 month of enrollment.
- the standard nutritional supplement contained: Water, Glucose Syrup, Sugar, Vegetable Oil (Canola, High Oleic Sunflower, Com), Milk Protein Concentrate, and less than 2% of Soy Protein Isolate, Calcium Caseinate, Sodium Caseinate, Gum Acacia,
- Fructooligosaccharides Inulin (from Chicory), Soy Lecithin, Salt, Natural and Artificial Flavor, Carrageenan Potassium Citrate, Calcium Phosphate, Magnesium Phosphate, Magnesium
- Chloride Sodium Ascorbate, Choline Bitartrate, DL- Alpha Tocopheryl Acetate, Ascorbic Acid, Potassium Chloride, Ferrous Sulfate, Zinc Sulfate, Niacinamide, Calcium Pantothenate,
- the RTDS contained: Water, Organic Date Syrup, Enzymatically Modified Almond Oil, Enzymatically Hydrolyzed Pea Protein, Soluble Corn Fiber, Cocoa Powder, Natural Flavors, Salt, Vitamin C, Vitamin E (dl-alpha-tocopheryl acetate), Niacinamide, Pantothenic acid (calcium-D-pantothenate), Vitamin B6 (pyridoxine hydrochloride), Vitamin A (retinyl palmitate), Vitamin B2 (riboflavin), Vitamin B1 (thiamine hydrochloride), L-methylfolate, Vitamin Kl, Vitamin D3 (cholecalciferol), Biotin, Vitamin B 12 (cyanocobalamin).
- the nutritional supplement was 5.9% fat, 5.9% protein and 19% carbs by weight while the RTDS was 7.4% fat, 4.7% protein and 9.8% carbs by weight.
- the dosage of lipid was 0.5g/kg body weight.
- the lipid in the standard nutritional supplement was a blend of TAGs from canola, high oleic sunflower and com oil. In the interventional drink the MAGs were produced from almond oil.
- the dosage of lipid for each patient was based upon well-established“Lipid Tolerance Tests”, which are similar in design and scope to well-known glucose tolerance tests. The recommended dosage for these tests is 0.5 -1.0 g/kg administered over 20 -30 minutes. Samples were taken at the start of the test and hourly for 6 hours. Serum triglyceride levels were measured using standard laboratory methods.
- the PERT dosage used in the study followed the manufacturer’s recommended dosage guidelines of 2,500 iu of lipase activity per gram of fat ingested. This translated to 3-4 capsules during the crossover stage of the study.
- FIGURE 7 depicts the increase in serum triglycerides following ingestion of the EMO-based ready-to-drink shake in two patients.
- the dashed lines represent patients that received 0.5 g per Kg of body weight of enzyme-modified almond oil and the solid lines represent patients that received 0.5 g per Kg of body weight of canola, high oleic sunflower and com oil incorporated into the RTDS consumed over a half-hour period.
- FIGURE 7 illustrates that the enzyme-modified oil in the RTDS was absorbed by the patients and converted into serum triglycerides.
- FIGURE 8 depicts the increase in serum triglycerides in another patient following ingestion of the test drinks.
- the dashed line represents serum triglycerides following ingestion of MAG-based RTDS without PERT and the solid line represents standard of care RTDS with PERT.
- the patients received 0.5 g per Kg of body weight of enzyme- modified almond oil or 0.5 g per Kg of body weight of com oil, incorporated in the RTDS consumed over a half-hour period.
- Bile acids from the liver are required for this activity.
- the TAGs in the standard of care drink could not be emulsified into the micro-emulsions required for optimal lipase activity in the small intestine, and thus serum triglycerides did not increase as quickly as with the MAG formulation, which does not require lipase activity.
- the actual dosage of lipids per patient was the same in all cases: 0.5 g/kg body mass.
- FIGURE 9 depicts the increase in serum glucose averaged from 8 patients from each of Arm 1 and Arm 2 in the study over the six hour sampling period. Patients who consumed the RTDS showed a pronounced decrease in maximum post-prandial serum glucose and remained below the standard nutritional supplement cohort.
- EMO-based nutritional supplement which is high in 1-monoacylglycerols such as 1-oleyl monoglycerol, was able to positively impact glucose homeostasis compared to the standard nutritional supplement with PERT which would only be expected to yield a small amount of 2- monoacylglycerols such as 2-oleyl monoglycerol.
- 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.
- a high calorie RTDS can be prepared as follows: Add DI water (-60% of final volume) into main mixing vessel, and heat water to -60° C. Mix in Hydrolyzed Protein, then add Agave syrup. Use hand mixer to combine. In a separate container, combine warm (60° C) EMO and lecithin. When lecithin has dissolved, add EMO/Lecithin to aqueous phase & mix. Add additional water to achieve final weight (volume). Emulsify with shear blender. To prepare a very high calorie RTDS, add higher levels of the components.
- This method can also be used to produce high calorie products in semi-solid formats such as puddings, mousses,“popsicles” and ice cream-like products using the beverage base recipe and adding viscosity altering agents such as xanthan gum and gum acacia.
- a high calorie bar can be prepared as follows: Add DI water (-60% of final volume) into main mixing vessel, and heat water to -60° C. Mix in Hydrolyzed Protein, then add Agave syrup. In a separate container, combine warm (60° C) EMO and lecithin with hand mixer. When lecithin has dissolved, add EMO/Lecithin to aqueous phase & mix. Add additional water to achieve final weight (volume).
- 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
- Enzyme modified almond oil was prepared as described in Example 6.
- AOCS Official Method Cd 29b-13 (Revised 2017) - 2- and 3-MCPD Fatty Acid Esters and Glycidol Fatty Acid Esters in Edible Oils and Fats by Alkaline Transesterification and GC/MS. This method is used for the determination of fatty acid esters of 2-chloropropane- 1,3-diol (2-MCPD), 3 -chloropropane- 1 ,2-diol (3-MCPD) and glycidol in edible oils and fats. See also AOCS Official Methods Cd 29a-13 or Cd 29c-13.
- Bound glycidol is the sum of all glycidyl derivatives that are cleaved by alkaline-catalyzed alcoholysis. The content of bound glycidol is reported in milligrams per kilogram (mg/kg).
- Bound 2-MCPD is the sum of all 2-MCPD- derivatives that are cleaved by alkaline-catalyzed alcoholysis. The content of bound 2-MCPD is reported in milligrams per kilogram (mg/kg).
- Bound 3-MCPD is the sum of all 3-MCPD- derivatives that are cleaved by alkaline-catalyzed alcoholysis. The content of bound 3-MCPD is reported in milligrams per kilogram (mg/kg).
- This method describes a procedure for the parallel determination of glycidol together with 2-MCPD and 3-MCPD present in bound or free form in oils and fats.
- the method is based on alkaline-catalyzed ester cleavage, transformation of the released glycidol into monobromopropanediol (MBPD) and derived free diols (MCPD and MBPD) with phenylboronic acid (PBA).
- MBPD monobromopropanediol
- MCPD and MBPD derived free diols
- PBA phenylboronic acid
- the total 2-MCPD (free and bound) and 3-MCPD (free and bound) in the starting oil was 0.65 mg/kg and 1.17 mg/kg, respectively.
- the enzyme modified almond oil (Example 6) had a total 2-MCPD (free and bound) and 3-MCPD (free and bound) each of ⁇ 0.10 mg/kg, which is below the limit of quantification of the assay to measure MCPD (0.10 mg/kg).
- the sums of the total detected MCPD in the starting almond oil and in the enzyme modified oil was 1.82 mg/kg and ⁇ 0.10 mg/kg, respectively.
- MCT, canola and almond oils were processed according to the manufacturing method of the present disclosure. Fatty acid profiles for each were measured in both the starting oil and the MAG oil as shown in Table 9 below.
- Fatty acids were analyzed after derivatization as the fatty acid methyl esters and compared to standards.
- a sample 500 ml was added to a 5-ml reaction tube containing 2 ml boron trifluoride solution (12% in methanol), 20 ml dimethoxypropane and 100 ml of a tridecanoic acid internal standard solution (10 mg/ml).
- the reaction tube was vortexed and incubated in a heating block at 60°C for 30 minutes.
- the reaction tube was removed from the heating block and allowed to cool for 15 minutes.
- 1 ml of distilled water was added to quench the reaction, followed by 1 ml of hexane.
- the reaction tube was vortexed for 60 seconds and the phases were allowed to separate for 3 minutes.
- the top (hydrophobic) phase was removed to a 1.5-ml tube containing about 50 mg sodium sulfate (anhydrous).
- the 1.5-ml tube was centrifuged and ⁇ 500 ml of the clarified, dried hydrophobic phase was transferred to a gas chromatography sample vial.
- Samples were analyzed using an Agilent 7890A gas chromatograph with Flame ionization detector and Agilent Openlab CDS Chemstation software.
- both the starting oil and MAG oil contained substantially the same fatty acid profiles.
- Example 13 The EMO Process conservees Essential Fatty Acids Found in Original Oil
- Canola EMO was produced as described in Example 1. Fatty acids were measured as described in Example 2. Results of the fatty acid analysis are shown in FIGURE 11. Canola oil and the EMO produced from the canola oil mtaining the integrity of the fatty acid profile and include the essential fatty acids linoleic and linolenic acids. Similar results were obtained with EMO from olive oil, sunflower oil and almond oil.
- Example 14 Beneficial Compounds are Preserved [00216] Vegetable oils contain trace quantities of many lipids, steroids, esters and phenolic compounds that contribute to the taste and health benefits of the oils. Many of these compounds are preserved or enriched in the EMO process. This is illustrated in FIGURES 12A- 12B. Canola EMO was prepared as described in Example 1. Lipid samples were derivatized with 3-picolylamide for LC/MS/MS analysis. In brief, 150 mL of standard (0.1-100 mg/mL) and 20 mL of internal standard mixture were mixed and dried under nitrogen.
- LC-MS analysis was in Ionization mode: positive (total fatty acid & lipidomics) & negative (lipidomics) ionization.
- Software used for analysis Thermo Scientific Freestyle & LipidSearch.
- Orbitrap fusion method data dependent acquisition MS 2 (total fatty acid) & MS.
- Glycosphingolipids e.g.
- Glycoglycerolipids e.g. Monogalactodiacylglycerol
- Phosphatidylmethanol e.g. Sitosteryl ester
- Neutral lipids e.g. Campesterol ester
- Sphingolipids phosphatidyl glycerol ,wax esters and sphingomyelin. Coenzyme was also found to be enhanced.
- a food product comprises an oil and has a total caloric content of from about 25 kcal to about 1,000 kcal, wherein from about 5% to about 75% of the total caloric content is derived from said oil, and wherein the oil comprises less than 10% by weight triacylglycerides (TAGs) based on the total weight of the oil, wherein the oil is substantially free of monochloropropandiol (MCPD).
- TAGs triacylglycerides
- the oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the oil.
- MAGs monoacylglyceride
- the oil comprises greater than 60% by weight MAGs based on the total weight of the oil.
- the oil comprises greater than 70% by weight MAGs based on the total weight of the oil.
- the oil comprises greater than 80% by weight MAGs based on the total weight of the oil.
- the oil comprises greater than 90% by weight MAGs based on the total weight of the oil.
- the food product further comprises a carbohydrate source.
- the food product further comprises a carbohydrate source and the carbohydrate source comprises a fruit or agave syrup.
- the food product further comprises a carbohydrate source and the carbohydrate source comprises simple sugars.
- the food product further comprises a carbohydrate source and from about 20% to about 50% of calories are derived from the carbohydrate source.
- the food product comprises a carbohydrate source and further comprises a protein source.
- the food product comprises a carbohydrate source and further comprises a protein source, and from about 10% to about 50% of calories are derived from the protein source.
- the food product comprises a carbohydrate source and further comprises a protein source
- the protein source comprises an hydrolyzed or partially hydrolyzed protein
- the food product comprises a carbohydrate source and further comprises a protein source
- the protein source comprises an hydrolyzed or partially hydrolyzed protein, wherein the hydrolyzed protein is selected from hydrolyzed pea protein and a whey-based hydrolysate product.
- the food product further comprises a protein source.
- the food product further comprises a protein source, wherein from about 10% to about 50% of calories are derived from the protein source.
- the food product further comprises a protein source, wherein the protein source comprises an hydrolyzed or partially hydrolyzed protein.
- the food product further comprises a protein source, wherein the protein source comprises an hydrolyzed or partially hydrolyzed protein, and wherein the hydrolyzed protein is selected from hydrolyzed pea protein and a whey-based hydrolysate product.
- the oil is a processed oil derived from an oil source.
- the oil is a processed oil derived from an oil source, wherein 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 oil is a processed oil derived from an oil source, wherein 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, and wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof.
- the oil is a processed oil derived from an oil source, wherein 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, wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof, and wherein the antioxidant is tocopherol.
- the oil is a processed oil derived from an oil source, wherein 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, wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof, wherein the antioxidant is tocopherol, and wherein said tocopherol is selected from a-tocopherol, b-tocopherol, d-tocopherol, g- tocopherol, a-tocotrienol, b-tocotrienol, d-tocotrienol, and g-tocotrienol.
- a food product comprises a processed oil, a
- carbohydrate source and a protein source, and having a total weight from about 25 grams to about 500 grams with a caloric density of from about 1 kcal per gram to about 5 kcal per gram, wherein the processed oil comprises from about 10% to about 50% of the total caloric content, and wherein the processed oil has a MAG content of equal to or greater than 40% by weight based on the total weight of the processed oil and a TAG content of equal to or less than 10% by weight based on the total weight of the processed oil, and wherein the processed oil has less than 0.10 mg/kg MCPD.
- a product comprises a processed oil derived from an oil source, wherein the processed oil comprises a MAG content equal to or greater than 40% by weight of the total weight of the processed oil, wherein the processed oil is either free of TAGs or comprises a TAG content that is equal to or less than 10% by weight of the total weight of the processed oil, and wherein 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, wherein the oil source comprise from about 1.00 mg/kg to about 12.00 mg/kg MCPD, and wherein the processed oil comprises less than 0.100 mg/kg MCPD.
- said oil source is from an origin selected from a plant an animal, algae or fish.
- said oil source is of plant origin.
- said oil source is selected from the group consisting of olive oil, sunflower oil, com oil, almond oil, rapeseed oil, palm oil, soybean oil, flaxseed oil, and mixtures thereof.
- the non-oil ingredients are selected from the group consisting of antioxidants, vitamins, and mixtures thereof.
- the non-oil ingredients are selected from the group consisting of antioxidants, vitamins, and mixtures thereof and the antioxidant is tocopherol.
- the non-oil ingredients are selected from the group consisting of antioxidants, vitamins, and mixtures thereof, the antioxidant is tocopherol, and the tocopherol is selected from the group consisting of a-tocopherol, b-tocopherol, d-tocopherol, g-tocopherol, a-tocotrienol, b- tocotrienol, d-tocotrienol, and g-tocotrienol.
- the 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 processed oil comprises a MAG content of from about 50% to about 95% by weight based on the total weight of the processed oil, and the processed oil comprises a TAG content from about 5% to about 0.5% by weight based on the total weight of the processed oil.
- the processed oil comprises a TAG content from about 5% to about 0.5% by weight based on the total weight of the processed oil.
- a method for making a monoacylglycerol-enriched oil comprises: mixing a starting oil comprising triacylglycerols (TAGs) and from about 1.00 mg/kg to about 12.00 mg/kg of MCPD, wherein the TAGs are in an amount greater than 50% by weight based on the total weight of the starting oil, a buffer solution and a first enzyme capable of hydrolyzing said TAGs to free fatty acids (FFAs) to yield a first reaction mixture; allowing said first reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs for a first period of time to yield an aqueous phase and a first lipid reaction product comprising FFAs; inactivating said first enzyme in said first lipid reaction product; collecting said first lipid reaction product by removing it from the aqueous phase; mixing said first lipid reaction product with a food-grade glycerol and a second enzyme capable of esterifying FFAs to form a second reaction
- TAGs triacylglyce
- the starting oil is an oil derived from plant, animal or fish origin.
- the starting oil is a plant oil or a mixture of plant oils.
- the starting oil is a plant oil selected from the group consisting of olive oil, sunflower oil, com oil, almond oil, rapeseed oil, palm oil, soybean oil, flaxseed oil, and mixtures thereof.
- said first enzyme is a lipase.
- said first enzyme is lipase AY.
- said buffer solution is a sodium citrate solution.
- said first period of time is a period of time sufficient to hydrolyze at least 94% of the TAGs in said starting oil.
- said first period of time is between about 14 and about 24 hours.
- said step of allowing said reaction mixture to react under conditions sufficient for said first enzyme to hydrolyze said TAGs is performed at a temperature between about 30°C and about 35°C.
- 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 second enzyme is a lipase.
- said second enzyme is lipase G.
- said second period of time is a period of time sufficient to result in enrichment of MAGs in the lipid oil phase of about 60% to 95%.
- said second period of time is between about 24 hours and about 72 hours.
- said step of allowing said second reaction mixture to react for a second period of time to yield a lipid oil phase and a glycerol phase is performed at a temperature between about 17°C and 23°C.
- the method further comprises drying said second lipid reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of water from the second lipid reaction product.
- the method further comprises drying said second lipid reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of water from the second lipid reaction product, wherein said step of drying said second lipid reaction product is performed at a temperature between 20°C-30°C.
- the method further comprises drying said second lipid reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of water from the second lipid reaction product, wherein said drying step is applied throughout the second period of time.
- said step of inactivating said second enzyme is performed by heating said second lipid reaction product.
- said step of inactivating said second enzyme is performed by heating said second lipid reaction product, wherein said heating is performed at a temperature of at least 70°C for at least 1 hour.
- said step of separating said lipid oil phase from said glycerol phase comprise adding sodium chloride to said second lipid reaction product.
- said step of separating said lipid oil phase from said glycerol phase comprise adding sodium chloride to said second lipid reaction product, wherein the final concentration of sodium chloride comprises up to 0.3 weight percent sodium chloride.
- the method further comprises before mixing said first lipid reaction product and food-grade glycerol and a second enzyme capable of esterifying FFAs and glycerol, reestablishing a nitrogen atmosphere over said first lipid reaction product.
- the method further comprises adding tocopherol to said lipid oil phase after collecting said lipid oil phase.
- the lipid oil phase comprises MAGs in an amount from about 40% to about 99% by weight based on the total weight of the lipid oil phase and wherein the lipid oil phase either is free of TAGs or comprises TAGs in an about from about 0.1% to about 10% by weight based on the total weight of the lipid oil phase.
- a processed oil comprises oleic acid monolgyceride (MOG) and having a total fatty acid content, wherein said MOG contributes between about 5% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monolgyceride
- the processed oil comprises less than 10% by weight triacylglycerides (TAGs) based on the total weight of the processed oil.
- the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 60% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 70% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 80% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 90% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil is processed oil derived from an oil source.
- the processed oil is processed oil derived from an oil source, and 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 processed oil is processed oil derived from an oil source, and 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, wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof.
- the processed oil is processed oil derived from an oil source, and 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, wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof, and wherein the antioxidant is tocopherol.
- the processed oil is processed oil derived from an oil source, and 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, wherein the non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof, wherein the antioxidant is tocopherol, and wherein said tocopherol is selected from a-tocopherol, b- tocopherol, d-tocopherol, g-tocopherol, a-tocotrienol, b-tocotrienol, d-tocotrienol, and g- tocotrienol.
- the processed oil is substantially free of monochloropropandiol (MCPD).
- the processed oil has less than 0.10 mg/kg monochloropropandiol (MCPD).
- said oil source is from an origin selected from a plant, an animal, algae or fish.
- said oil source is of plant origin.
- said oil source is selected from the group consisting of safflower oil, grape oil, Silybum marianum oil, hemp oil, sunflower oil, wheat germ oil, pumpkin seed oil, sesame oil, rice bran oil, almond oil, rapeseed oil, peanut oil, olive oil, and coconut oil.
- 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.
- said processed oil comprises a TAG content from about 5% to about 0.5% by weight based on the total weight of the processed oil.
- the MOG in said processed oil comprises at least 50% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in said processed oil comprises at least 60% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in said processed oil comprises at least 70% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in said processed oil comprises at least 80% 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 1.5% to about 90% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises linoleic acid, wherein said linoleic acid is present in said processed oil in an amount of about 10% to about 90% by weight out of the total fatty acid content of the processed oil.
- 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.
- the processed oil further comprises linoleic acid, wherein said linoleic acid is present in said processed oil in an amount of about 10% to about 25% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises linolenic acid, wherein said linolenic acid is present in said processed oil in amount of about 0.01% to about 2% by weight out of the total fatty acid content of the processed oil.
- a ratio between the amount of oleic acid and linoleic acid in said processed oil is between about 0.01 and about 5.
- a ratio between the amount of oleic acid and linoleic acid in said processed oil is between about 1 and about 4.
- a ratio between the amount of oleic acid and linolenic acid in said processed oil is between about 1 and about 100.
- a ratio between the amount of oleic acid and linolenic acid in said processed oil is between about 10 and 100.
- a ratio between the amount of oleic acid and linolenic acid in said processed oil is between about 10 and 30.
- said fatty acid profile comprises oleic acid, linoleic acid and linolenic acid.
- the amount of oleic acid, linoleic acid and linolenic acid in the processed oil is within about 10% of the amount of oleic acid, linoleic acid and linolenic acid, respectively, in the pre-processed oil from which the processed oil was produced.
- 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.
- the processed oil comprises three times the amount of MAGs relative to the amount of TAGs in the pre-processed oil from which the processed oil was produced.
- the processed oil comprises oleic acid in the form of oleic acid monoglyceride in an amount that is about the same as the amount of oleic acid 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 linolenic acid in the processed oil is within about 10% 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 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 processed oil comprises oleic acid and linoleic acid, wherein a ratio of oleic acid to linoleic acid in the processed oil is between about 0.01 and about 5, and wherein the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the ratio of oleic acid to linoleic acid in the processed oil is between about 1 and about 4.
- the ratio of oleic acid to linoleic acid in the processed oil is between about 3 and about 4.
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 1 and about 100.
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 100.
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 30.
- a processed oil comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 1 and about 100, 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 processed oil comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 100, 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 processed oil comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 30, and wherein the processed oil comprises greater than 50% by weight
- MAGs monoacylglyceride
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linoleic acid in the processed oil is between about 0.01 and about 5.
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linoleic acid in the processed oil is between about 1 and about 4.
- the processed oil further comprises linoleic acid, wherein a ratio of oleic acid to linoleic acid in the processed oil is between about 3 and about 4.
- oleic acid monoglyceride MOG
- At least a portion of said oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 50% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- MOG oleic acid monoglyceride
- 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
- At least a portion of said oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 70% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- MOG oleic acid monoglyceride
- At least a portion of said oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 80% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- MOG oleic acid monoglyceride
- the processed oil comprises less than 10% by weight triacylglycerides (TAGs) based on the total weight of the processed oil.
- TAGs triacylglycerides
- the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 60% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 70% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 80% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 90% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil is derived from an oil source.
- 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.
- non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof.
- said antioxidant is tocopherol.
- said tocopherol is selected from a- tocopherol, b-tocopherol, d-tocopherol, g-tocopherol, a-tocotrienol, b-tocotrienol, d-tocotrienol, and g-tocotrienol.
- the processed oil is substantially free of monochloropropandiol (MCPD).
- the processed oil has less than 0.10 mg/kg monochloropropandiol (MCPD).
- the oil source is from an origin selected from a plant, an animal, algae or fish.
- said oil source is of plant origin.
- said oil source is selected from the group consisting of safflower oil, grape oil, Silybum mariamm oil, hemp oil, sunflower oil, wheat germ oil, pumpkin seed oil, sesame oil, rice bran oil, almond oil, rapeseed oil, peanut oil, olive oil, and coconut oil.
- 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.
- said processed oil comprises a TAG content from about 5% to about 0.5% by weight based on the total weight of the processed oil.
- said processed oil has a fatty acid profile that is substantially the same as a fatty acid profile of the pre-processed oil from which the processed oil was produced.
- said fatty acid profile comprises oleic acid, linoleic acid and linolenic acid
- the amount of oleic acid, linoleic acid and linolenic acid in the processed oil is within about 10% of the amount of oleic acid, linoleic acid and linolenic acid, respectively, in the pre-processed oil from which the processed oil was produced.
- 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.
- the processed oil comprises three times the amount of MAGs relative to the amount of TAGs in the pre-processed oil from which the processed oil was produced.
- the processed oil comprises oleic acid in the form of oleic acid monoglyceride in an amount that is about the same as the amount of oleic acid in the pre-processed oil from which the processed oil was produced.
- a processed oil comprises oleic acid and linoleic acid and having a total fatty acid content, wherein said linoleic acid is present in an amount from about 10% to about 90% by weight out of the total fatty acid content of the processed oil, and wherein the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- said linoleic acid is present in an amount from about 20% to about 90% by weight out of the total fatty acid content of the processed oil.
- said linoleic acid is present in an amount from about 10% to about 25% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises linolenic acid, wherein said linolenic acid is present in an amount from about 0.01% to about 2% by weight out of the total fatty acid content of the processed oil.
- a ratio of oleic acid to linoleic acid in the processed oil is between about 0.01 and about 5.
- a ratio of oleic acid to linoleic acid in the processed oil is between about 1 and about 4.
- a ratio of oleic acid to linoleic acid in the processed oil is between about 3 and about 4.
- a ratio of oleic acid to linolenic acid in the processed oil is between about 1 and about 100.
- a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 100.
- a ratio of oleic acid to linolenic acid in the processed oil is between about 10 and about 30.
- the MOG in the processed oil comprises at least 50% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in the processed oil comprises at least 60% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in the processed oil comprises at least 70% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the MOG in the processed oil comprises at least 80% by weight 1-oleyl monoglyceride out of the total amount of MOG.
- the processed oil comprises less than 10% by weight triacylglycerides (TAGs) based on the total weight of the processed oil.
- TAGs triacylglycerides
- the processed oil comprises greater than 50% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 60% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- the processed oil comprises greater than 70% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- the processed oil comprises greater than 80% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil comprises greater than 90% by weight monoacylglyceride (MAGs) based on the total weight of the processed oil.
- MAGs monoacylglyceride
- the processed oil is processed oil derived from an oil source.
- 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.
- non-oil ingredients are selected from antioxidants, vitamins, and mixtures thereof.
- said antioxidant is tocopherol.
- said tocopherol is selected from a- tocopherol, b-tocopherol, d-tocopherol, g-tocopherol, a-tocotrienol, b-tocotrienol, d-tocotrienol, and g-tocotrienol.
- the processed oil is substantially free of monochloropropandiol (MCPD).
- the processed oil has less than 0.10 mg/kg monochloropropandiol (MCPD).
- said oil source is from an origin selected from a plant, an animal, algae or fish.
- the oil source is of plant origin.
- said oil source is selected from the group consisting of safflower oil, grape oil, Silybum mariamm oil, hemp oil, sunflower oil, wheat germ oil, pumpkin seed oil, sesame oil, rice bran oil, almond oil, rapeseed oil, peanut oil, olive oil, and coconut oil.
- 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.
- said processed oil comprises a TAG content from about 5% to about 0.5% by weight based on the total weight of the processed oil.
- said processed oil has a fatty acid profile that is substantially the same as a fatty acid profile of the pre-processed oil from which the processed oil was produced.
- said fatty acid profile comprises oleic acid, linoleic acid and linolenic acid.
- the amount of oleic acid, linoleic acid and linolenic acid in the processed oil is within about 10% of the amount of oleic acid, linoleic acid and linolenic acid, respectively, in the pre-processed oil from which the processed oil was produced.
- 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.
- the processed oil comprises about the same amount of MAGs relative to the amount of TAGs in the pre-processed oil from which the processed oil was produced.
- the processed oil comprises oleic acid in the form of oleic acid
- a processed oil has a fatty acid profile comprising oleic acid, linoleic acid and linolenic acid, wherein the amount of olric acid, linoleic acid and linolenic acid in the processed oil is within about 10% 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
- MAGs monoacylglyceride
- 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 promoting glucose homeostasis in a subject in need thereof comprises: administering to said subject a composition comprising a processed oil.
- a method for treating type II diabetes in a subject in need thereof comprises: administering to said subject a composition comprising a processed oil.
- a method for promoting glucose homeostasis 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
- 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
- At least 60% by weight of said MOG is 1-oleyl monoglyceride.
- At least 70% by weight of said MOG is 1-oleyl monoglyceride.
- At least 80% by weight of said MOG is 1-oleyl 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 composition is a food product comprising the processed oil of a food product of any of the first, second or third embodiment and any of the foregoing aspects thereof.
- said subject is suffering from a condition that affects glucose homeostasis.
- the condition is insulin resistance or type P diabetes.
- said MOG contributes between about 10% and about 75% by weight of the total fatty acid content of the processed oil.
- said MOG contributes between about 20% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG contributes between about 30% and about 75% by weight of the total fatty acid content of the processed oil.
- said MOG contributes between about 40% and about 75% by weight of the total fatty acid content of the processed oil.
- said MOG contributes between about 50% and about 75% by weight of the total fatty acid content of the processed oil.
- said MOG contributes between about 60% and about 75% by weight of the total fatty acid content of the processed oil.
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes 5% to about 75% by weight of the fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 10% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 20% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 30% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 40% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 50% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- said processed oil comprises oleic acid monoglyceride (MOG) in an amount that contributes between about 60% and about 75% by weight of the total fatty acid content of the processed oil.
- MOG oleic acid monoglyceride
- a processed oil has a fatty acid profile wherein the fatty acid profile of the processed oil is substantially the same as 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 food product comprises the processed oil of any one of the fifth, sixth, seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth or fourteenth embodiment or any of the foregoing aspects of the fifth, sixth, seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth or fourteenth embodiments.
- a processed oil comprises greater than 50% 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 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 70% 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 80% 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 5% 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 10% 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 20% to about 75% by wright out of the total fatty acid content of the processed oil.
- the processed oil further comprises oleic acid in amount of from about 30% 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 40% 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 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 linoleic acid in an amount of from about 1.5% to about 90% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises linoleic acid in an amount of from about 10% to about 25% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises linolenic acid in an amount of from about 0.1% to about 2% by weight out of the total fatty acid content of the processed oil.
- the processed oil further comprises oleic acid and linoleic acid, wherein a ratio of oleic acid to linoleic acid is between about 0.01 and 5.
- the processed oil further comprises oleic acid and linoleic acid, wherein a ratio of oleic acid to linoleic acid is between about 1 and 4.
- the processed oil further comprises oleic acid and linoleic acid, wherein a ratio of oleic acid to linoleic acid is between about 3 and 4.
- the processed oil further comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid is between about 1 and 100.
- 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.
- the processed oil further comprises oleic acid and linolenic acid, wherein a ratio of oleic acid to linolenic acid is between about 10 and 30.
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Abstract
Description
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US201962794412P | 2019-01-18 | 2019-01-18 | |
US201962833558P | 2019-04-12 | 2019-04-12 | |
PCT/US2020/014182 WO2020150661A1 (en) | 2019-01-18 | 2020-01-17 | Method of making monoacylglyceride oils and food products containing monoacylglyceride oils |
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EP (1) | EP3911164A1 (en) |
JP (1) | JP2022517271A (en) |
CN (1) | CN113747796A (en) |
AU (1) | AU2020207945A1 (en) |
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JP2024515611A (en) * | 2021-04-13 | 2024-04-10 | グリコスバイオ インコーポレーテッド | Drug delivery using monoacylglycerol and free fatty acid based compositions |
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JP4391673B2 (en) * | 2000-08-08 | 2009-12-24 | 花王株式会社 | Oil composition |
US20040209953A1 (en) * | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
EP2643445B1 (en) * | 2010-11-23 | 2019-01-30 | Cargill, Incorporated | Lipid-based wax compositions substantially free of fat bloom and methods of making |
CA3060716A1 (en) * | 2017-05-08 | 2018-11-15 | Bunge Loders Croklaan B.V. | Emulsifier composition obtainable from free fatty acids |
WO2019075307A1 (en) * | 2017-10-13 | 2019-04-18 | Glycosbio Food Sciences, Inc. | Method of making monoacylglyceride oils and food products containing monoacylglyceride oils |
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WO2020150661A1 (en) | 2020-07-23 |
CN113747796A (en) | 2021-12-03 |
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