Method of making monoacylglyceride oils and food products containing monoacylglyceride oils

Abstract

To provide processed oils with a high monoacylglyceride (MAG) content and foods incorporating the processed oils.SOLUTION: There is provided a processed oil comprising monoacylglycerol (MAG), diacylglycerol (DAG), and free fatty acids (FFA), wherein MAG constitutes from about 30 wt.% to about 90 wt.% of the total weight of the processed oil, wherein DAG constitutes from about 10 wt.% to about 30 wt.% of the total weight of the processed oil, wherein FFA constitutes from about 5 wt.% to about 60 wt.% of the total weight of the processed oil, and further comprising non-oil ingredients that are naturally present in the processed oil, and wherein the processed oil is substantially free of monochloropropandiol (MCPD).SELECTED DRAWING: None

Description

Technical Field

[0001] Cross - Reference to Related Applications This application claims the benefit of U.S. Provisional Application No. 62 / 794,412, filed on Jan. 18, 2019, and U.S. Provisional Application No. 62 / 833,558, filed on Apr. 12, 2019, the entire contents of each of which are hereby incorporated by reference in their entirety.

[0002] Technical Field The present invention relates to a method for producing monoacylglycerol oil and a food containing monoacylglycerol oil.

Background Art

[0003] Chronic deficiency in the secretion of digestive enzymes by the pancreas is called exocrine pancreatic insufficiency (EPI). Without these digestive enzymes, patients suffering from EPI cannot properly digest nutrients in food and may suffer from malnutrition and abdominal disorders. EPI is common in individuals with chronic pancreatitis and several other chronic gastrointestinal disorders. EPI also appears in patients suffering from cystic fibrosis. Pancreatic enzyme replacement therapy (PERT) can reduce the effects of EPI, and individuals take enzyme capsules each time they consume food. Conventionally, PERT treatments contain pancreatic enzymes extracted from porcine pancreas.

[0004] Lipids are high - energy - density compounds and a source of essential long - chain fatty acids. Typically, consumed lipids containing a high proportion of triacylglycerol (TAG) are digested by lipase secreted from the pancreas into free fatty acids (FFA) and monoacylglycerol (MAG). Blocking the release of lipase from the pancreas severely impairs the digestion of fats and oils containing triacylglycerol. In the case of patients suffering from EPI, this can lead to significant malnutrition because calories, essential fatty acids, and fat - soluble nutrients are trapped in undigested lipid particles and pass through the body.

[0005] There is a clinical need for alternative nutrient sources that can be consumed by individuals with EPI without the need for PERT supplementation.

[0006] Partially hydrolyzed fats and oils in the form of MAG do not require PERT and are readily absorbed by individuals with EPI. MAG oil-based products are being evaluated clinically as capsule-based nutritional supplements. However, capsules are utilized to avoid their unpleasant taste. For conventional sources of MAG oil, the starting oil is chemically or enzymatically treated to produce MAG, which is then extracted with a solvent and distilled to fractionate the MAG from other components of the starting oil. These MAG products contain very small amounts of contaminating free fatty acids (FFA), DAG (diacylglycerol), and TAG and are sold as relatively pure products containing substantially no other compounds. Thus, conventional sources of MAG oil often lack other natural compounds found in oils such as tocopherols.

[0007] There is a clinical need for nutritional products with a very high energy calorie density that can be consumed by individuals with inefficient or defective digestive systems. In addition to individuals with pancreatic pathologies (e.g., patients with cystic fibrosis, pancreatitis, and pancreatic cancer), other patients with diagnosed or undiagnosed exocrine pancreatic insufficiency (EPI) would benefit from the product. Furthermore, individuals with bile dysfunction (cholestasis) can benefit from "pre-digested" fats that do not require bile acids for emulsification. There are high-calorie "energy bars" and energy drinks on the market. However, these products are not suitable for individuals who cannot digest (hydrolyze) the fat in the product. To date, there have been no formulations of lipids in liquid (shake) and solid (bar) forms suitable for "PERT-free" use. These formulations would be a source of "Complete Nutrition" and could meet all of an individual's calorie and essential fatty acid requirements. Liquid nutrition could be in the form of an oral nutritional supplement (ONS) product for enteral nutrition products.

[0008] Therefore, there is a need for high calorie density foods that can be consumed by individuals with an inefficient or defective digestive system. This application describes a method for producing an edible enzyme-modified oil (EMO) that is substantially free of TAG.

[0009] 3-Monochloropropane-1,2-diol (MCPD) and glycidyl esters are formed during the refining of edible oils. These compounds are toxic to humans and need to be minimized in food. 3-MCPD is currently classified by the International Agency for Research on Cancer (IARC) as possibly carcinogenic to humans (Group 2B). Glycidol is classified by IARC and the US National Toxicology Program as probably carcinogenic to humans (Group 2A). Current standards recommend an exposure of less than 2 μg / kg body weight per day, which is less than 140 μg / day for a 70 kg male and less than 10 μg / day for a 5 kg (about 10 lb) infant.

[0010] MCPD compounds were first detected in acid (HCl) hydrolyzed proteins, but in 2008, the presence of MCPD esters in refined vegetable oils was discovered. It was found that the problem was widespread. Many edible oils are processed to remove components that have an adverse effect on appearance, taste, storage stability, safety, and consumer acceptance. Monoacyl and diacyl glycerols (MAG and DAG) in oils can react with chloride ions in the deodorization process to form 3-monochloropropane-1,2-diol (3-MCPD) esters and glycidyl esters (GE).

[0011] Table 1 below shows the levels of MCPD compounds in the sampling of edible oils in the United States (from Food Additives & Contaminants: Part A, 2013 Vol. 30, No. 12, 2081 - 2092).

Table 1

[0012] The estimated exposure of U.S. infants to 3-MCPD and glycidyl esters from the consumption of infant formula has recently been reported (J. Spungen et al. Food Additives & Contaminants: Part A 2018, VOL. 35, NO. 6, 1085-1092). In this analysis, FDA data on the concentrations of 3-MCPD and glycidyl esters (as 3-MCPD and glycidol equivalents, respectively) in a small convenience sample of infant formula were used to estimate exposure from the consumption of infant formula by infants aged 0 to 6 months. The estimated exposures to 3-MCPD and GE based on the average concentrations of all infant formulas were 7-10 and 2 μg / kg body weight / day, respectively. The estimated average exposures when consuming infant formula produced by individual manufacturers were 1-14 μg / kg body weight / day for 3-MCPD and 1-3 μg / kg for GE.

[0013] Therefore, there is a need for methods to reduce and eliminate these compounds in edible oils. The method of the present application for producing an edible enzyme-modified oil (EMO) substantially free of contaminants such as TAG and MCPD thus addresses this need.

[0014] Some vegetable oils are rich in oleic acid. These oils have demonstrated health benefits. Some of these may be due to oleic acid and oils rich in this fatty acid such as olive oil, almond oil, canola oil. Triolein is a TAG that is very rich in oleic acid, as exemplified below. Triolein is 100% esterified with oleic acid at all three positions of glycerol. The three positions are defined as "sn-1, sn-2 and sn-3". Sn is the "stereochemical number". [Chemical formula]

[0015] Considering the health benefits of these oils, there is a need for compositions and methods that provide the health benefits of these oils to individuals suffering from EPI and make the beneficial components of the oils more available. SUMMARY OF THE INVENTION

[0016] The present disclosure is directed to products comprising a processed oil derived from an oil source. In one embodiment, the processed oil comprises a MAG content of 30 wt% or more of the total weight of the processed oil, a DAG content of about 10 wt% to about 30 wt% of the total weight of the processed oil, and an FFA content of about 5 wt% to about 60 wt% of the total weight of the processed oil, the processed oil does not contain TAG or contains a TAG content of 5 wt% or less of the total weight of the processed oil, the processed oil is derived from an oil source and contains non-oil components that are naturally present in the oil source, such that no non-oil components are added to the processed oil.

[0017] In some embodiments, the oil source is derived from a source selected from plants, animals, fish, or mixtures thereof. In some embodiments, the oil source contains MCPD compounds. In these embodiments, the processed oil is substantially free of MCPD compounds.

[0018] In some embodiments, the non-oil components of the product are selected from antioxidants, vitamins, and mixtures thereof.

[0019] In some embodiments, the product contains more than 1 wt% MAG of the total weight of the product.

[0020] In some embodiments, the product contains more than 50 wt% MAG of the total weight of the product.

[0021] The present disclosure is also directed to foods. In one embodiment, the food contains an oil having a calorie density of about 1 kcal / g to about 5 kcal / g, and about 20% to about 50% of the calories are derived from the oil.

[0022] In some embodiments, the oil of the food is a processed oil derived from an oil source, and the processed oil has an MAG content of 30 wt% or more of the total weight of the processed oil, a DAG content of about 10 wt% to about 30 wt% of the total weight of the processed oil, and an FFA content of about 5 wt% to about 60 wt% of the total weight of the processed oil. The processed oil contains no TAG or contains a TAG content of about 5 wt% or less of the total weight of the processed oil. The processed oil is derived from an oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil.

[0023] In some embodiments, the oil source of the food is derived from a source selected from plants, animals, or fish.

[0024] In some embodiments, the non-oil components of the food are selected from antioxidants, vitamins, and mixtures thereof.

[0025] In some embodiments, the food contains more than 1 wt% MAG of the total weight of the product.

[0026] In some embodiments, the food contains more than 50 wt% MAG of the total weight of the product.

[0027] In some embodiments, the food has a total weight of about 25 grams to about 3000 grams.

[0028] In some embodiments, the food has a total calorie content of about 1 kcal to about 5 kcal per gram.

[0029] In some embodiments, the food may further contain a carbohydrate source.

[0030] In some embodiments, the food may further contain a protein source.

[0031] In some embodiments, the oil contributes 5% to 95% of the total calorie content of the food.

[0032] The present disclosure also relates to a method for producing an oil enriched in monoacylglycerol. In one embodiment, the method comprises mixing a starting oil containing triacylglycerol (TAG) with a buffer and a first enzyme capable of hydrolyzing the TAG into free fatty acids (FFA) to produce a first reaction mixture; reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG for a first period to produce a reaction product of an aqueous phase and a lipid (free fatty acid); inactivating the first enzyme in the reaction product; recovering the lipid reaction product; mixing the lipid reaction product with food-grade glycerol and a second enzyme capable of esterifying the FFA to form a second reaction mixture; reacting the second reaction mixture for a second period to produce a lipid oil phase and a glycerol phase of the reaction product; inactivating the second enzyme in the reaction product; adding a salt to the reaction, separating the lipid oil phase from the glycerol phase; and recovering the lipid oil phase.

[0033] In some embodiments, the starting oil is an oil derived from plants, animals, marine organisms, or mixtures thereof. In some embodiments, the starting oil contains MCPD compounds and the lipid oil phase is substantially free of MCPD compounds.

[0034] In some embodiments, the first enzyme is lipase AY.

[0035] In some embodiments, the first period is a period sufficient to hydrolyze at least 94% of the TAG in the starting oil.

[0036] In some embodiments, the first period is from about 14 hours to 24 hours.

[0037] In some embodiments, the step of reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG is carried out at a temperature of about 30°C to about 35°C.

[0038] In some embodiments, the step of mixing a starting oil containing triacylglycerol (TAG), a buffer, and a first enzyme capable of hydrolyzing the TAG into free fatty acids (FFA), and reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG into FFA is performed under a nitrogen atmosphere.

[0039] In some embodiments, the second enzyme is lipase G.

[0040] In some embodiments, the second period is a period sufficient to result in a concentration of MAG in the lipid oil phase of about 60% to 95%.

[0041] In some embodiments, the second period is from about 24 hours to about 72 hours.

[0042] In some embodiments, the step of reacting the second reaction mixture for a second period to produce a lipid oil phase and a glycerol phase is performed at a temperature of about 17°C to 23°C.

[0043] In some embodiments, the method further comprises drying the reaction product by applying a third period of vacuum sufficient to remove at least some of the water from the reaction product.

[0044] In some embodiments, the step of drying the reaction product is performed at a temperature of 20°C to 30°C.

[0045] In some embodiments, the drying step is applied throughout the second period.

[0046] In some embodiments, the step of inactivating the second enzyme is performed by heating the reaction product.

[0047] In some embodiments, the heating is performed at a temperature of at least 70°C for at least 1 hour.

[0048] In some embodiments, the step of separating the lipid oil phase from the glycerol phase comprises adding sodium chloride to the reaction product.

[0049] In some embodiments, the final concentration of sodium chloride comprises up to 0.3 weight percent sodium chloride.

[0050] In some embodiments, the method further comprises reconstructing a nitrogen atmosphere over the lipid reaction product prior to mixing the lipid reaction product with food grade glycerol and a second enzyme capable of esterifying FFA and glycerol.

[0051] In some embodiments, prior to performing the step of recovering the lipid reaction product, at least a portion of the aqueous phase is removed, at least a portion of the aqueous phase is replaced with about an equal volume of water, and the step of waiting for a second period is repeated.

[0052] In some embodiments, the method further comprises adding tocopherol to the lipid oil phase after recovering the lipid oil phase.

[0053] In some embodiments, a processed oil having a total fatty acid content comprises monoglyceryl oleate (MOG) in an amount that contributes from about 5 wt% to about 75 wt% of the total fatty acid content of the processed oil composition.

[0054] In some embodiments, the processed oil comprises oleic acid and linoleic acid in a ratio of about 0.01 to about 5 and has greater than 50 wt% monoacylglycerol (MAG) based on the total weight of the processed oil.

[0055] In some embodiments, the processed oil comprises oleic acid and linolenic acid in a ratio of about 1 to about 100 and has greater than 50 wt% monoacylglycerol (MAG) based on the total weight of the processed oil.

[0056] In some embodiments, the processed oil contains oleic acid and linoleic acid, has a total fatty acid content, and the linoleic acid is present in an amount of about 10 wt% to about 90 wt% of the total fatty acid content of the processed oil.

[0057] In some embodiments, 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 is produced.

[0058] In some embodiments, the processed oil has a fatty acid profile that includes oleic acid, linoleic acid, and linolenic acid, and the amounts of oleic acid, linoleic acid, and linolenic acid are within about 10% each of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0059] In some embodiments, the processed oil has a fatty acid profile that includes oleic acid, linoleic acid, and linolenic acid, and the amounts of oleic acid, linoleic acid, and linolenic acid are within about 1% each of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0060] In some embodiments, a method of promoting glucose homeostasis in a subject in need thereof includes administering to the subject a composition comprising a processed oil containing oleic acid monoglyceride, wherein at least 50 wt% of the oleic acid monoglyceride is 1-oleoyl monoglyceride.

[0061] In some embodiments, a method of treating a subject in need of treatment for type II diabetes includes administering to the subject a composition comprising a processed oil containing oleic acid monoglyceride, wherein at least 50 wt% of the oleic acid monoglyceride is 1-oleoyl monoglyceride.

[0062] In some embodiments, a method of promoting glucose homeostasis in a subject in need thereof includes administering to the subject a composition comprising the processed oil of the present disclosure.

[0063] In some embodiments, a method for treating a subject in need of treating diabetes comprises administering to the subject a composition comprising the processed oil of the present disclosure.

Brief Description of the Drawings

[0064]

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DETAILED DESCRIPTION OF THE INVENTION

[0065] It should be understood that both the foregoing general description and the following detailed description are merely exemplary and explanatory and do not limit the claimed invention. In this application, unless specifically stated otherwise, the use of the singular includes the plural, the words "a" or "an" mean "at least one", and the use of "or" means "and / or". Further, the use of the term "including", as well as other forms such as "includes" and "included", is not limiting. Also, terms such as "element" or "component" include both an element or component that includes one unit and an element or component that includes more than one unit, unless specifically stated otherwise.

[0066] The section headings used herein are for organizational purposes only and should not be construed as limiting the subject matter described. All documents or portions of documents cited in this application, including but not limited to patents, patent applications, articles, books, and papers, are hereby expressly incorporated by reference in their entirety for any purpose. If one or more of the incorporated documents and similar materials define terms in a way that conflicts with the definitions of terms in this application, this application prevails.

[0067] As used in the context of the present invention, "enriched" means having a higher amount than the starting material. For example, an oil enriched in MAG is an oil having a MAG content greater than the starting MAG content before the enrichment process, or an oil having a greater proportion of MAG than the proportion the starting oil had before the enrichment process. The enrichment process can be done by converting TAG to MAG, thereby increasing the content and proportion of MAG and decreasing the content or proportion of TAG.

[0068] Triacylglycerol (also known as triglyceride, "TAG") is a glyceride consisting of three fatty acid chains covalently bonded to a glycerol molecule via ester linkages. TAG may be classified as having a long or medium chain length. Long-chain TAG contains fatty acids having 14 or more carbons, and medium-chain TAG contains fatty acids having 6 - 12 carbons. Long-chain TAG can contain ω3 and ω6 fatty acids. Medium-chain TAG does not contain ω3 or ω6 fatty acids because it has saturated fatty acids. Long-chain TAG (LCT) and medium-chain triglyceride (MCT) can serve as an energy source.

[0069] Diacylglycerol (also known as diglyceride, "DAG") is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule via ester linkages.

[0070] Monoacylglycerol (also known as monoglyceride, "MAG") is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule via an ester linkage.

[0071] As used herein, the term "processed oil" refers to a non-natural oil composition that substantially does not contain TAG or has a reduced amount of TAG relative to a pre-modified or pre-processed oil.

[0072] As used herein, the term "enzyme-modified oil" or "EMO" refers to a processed oil in which, for example, using the enzyme conversions of the present disclosure, TAG has been enzymatically converted to MAG.

[0073] As used herein, the term "food" refers to manufactured or non-natural food. The food referred to herein is manufactured as a whole and is non-natural, but can include various combinations of natural ingredients, it being understood that such combinations do not occur in nature or, if they do occur in nature, do not occur in the relative amounts in which they are used in food.

[0074] 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 present invention are used in experimental animals, including but not limited to rodents such as mice, rats, hamsters, and primates, in veterinary applications, and in the development of animal models of disease.

[0075] "Treatment" is an intervention that is intended to prevent the onset of a disorder or to change the pathology or symptoms of a disorder. Thus, "treatment" can refer to both therapeutic treatment and prophylactic or preventative measures. Those in need of treatment include those who already have a disorder and those in whom the disorder is to be prevented. In the treatment of tumors (e.g., cancer), a therapeutic agent can directly reduce the pathology of tumor cells or make the tumor cells more sensitive to treatment with other therapeutic agents (e.g., radiation therapy and / or chemotherapy).

[0076] As used herein, a "non-oil component" is a naturally occurring component in an oil source that is not MAG, DAG, TAG, FFA, or a lipid.

[0077] In some embodiments, the starting oil may include, but is not limited to, for example, plant-derived oils (such as olive oil, almond oil, canola oil, coconut oil, cottonseed oil, palm kernel oil, palm olein oil, palm stearin oil, peanut oil, linseed oil, sunflower seed oil, corn oil, grape seed oil, palm oil, soybean oil, etc.), or animal-derived oils (such as fish oil, sardine oil, or anchovy oil, or algal oil, etc.), or any mixture of the above-mentioned vegetable oils and / or animal oils. In one aspect, the starting oil includes a blend of olive oil, sunflower seed oil, and linseed oil, where about 50 wt% to about 80 wt% of the total weight of the starting oil is olive oil, about 10 wt% to about 30 wt% of the total weight of the starting oil is sunflower seed oil, and about 5 wt% to about 20 wt% of the total weight of the starting oil is linseed oil. In another aspect, about 50 wt% to about 80 wt% of the total weight of the starting oil is olive oil, about 10 wt% to about 30 wt% of the total weight of the starting oil is linseed oil, and about 5 wt% to about 20 wt% of the total weight of the starting oil is sunflower seed oil.

[0078] In some embodiments, the starting oil contains MCPD compounds. The MCPD compounds can be in an amount of about 0.30 mg / kg to about 12.0 mg / kg, or about 1.0 mg / kg to about 11.00 mg / kg, or about 2.00 mg / kg to about 10.50 mg / kg. Examples of starting oils containing MCPD compounds include almonds, canola, coconut, corn, cottonseed, grape seeds, olives, palms, palm kernels, palm olein, palm stearin, peanuts, soybeans, and sunflowers.

[0079] In some embodiments, the process of making a product enriched in MAG includes a first step of hydrolyzing TAG. Without limitation, for example, the hydrolysis of TAG can be carried out by lipases such as lipase AY (Amano Enzymes, USA Elgin IL, USA), or any non-positional specific lipase that cleaves at the sn-1, sn-2, and sn-3 positions.

[0080] In some embodiments, the first step of hydrolyzing TAG can be carried out at a temperature of about 30°C to 35°C. By way of example and not limitation, the first step of hydrolyzing TAG can be carried out at 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 at a temperature of 30°C, 31°C, 32°C, 33°C, 34°C, or 35°C.

[0081] In some embodiments, the first step of hydrolyzing TAG can be carried out for about 14 hours to 24 hours. By way of example and not limitation, the first step of hydrolyzing TAG can 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 for about 14 hours, 15 hours, 16 hours, 17 hours, 18 hours, 19 hours, 20 hours, 21 hours, 22 hours, 23 hours, or 24 hours.

[0082] In some embodiments, the first step of hydrolyzing TAG results in hydrolysis of substantially all of the TAG. By way of example and not limitation, the first step of hydrolyzing TAG 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% of the TAG, or at least 94%, 95%, 96%, 97%, 98%, 99%, or 100% of the TAG.

[0083] In some embodiments, the process of making a product enriched in MAG includes a second step of esterification with glycerol to enrich the MAG oil content. By way of non-limiting example, this second step of esterification can be carried out by a lipase, such as lipase G (Amano Enzymes, USA Elgin IL, USA), or any positional specific lipase that catalyzes esterification at the sn-1 position but does not effectively catalyze the formation of the second or third esters on glycerol (which produces DAG and TAG).

[0084] In some embodiments, the second step of esterification with glycerol to enrich the MAG oil content results in enriching the MAG in the product to about 70% - 95%. By way of non-limiting example, the MAG oil content can be enriched to 70% - 95%, 75% - 95%, 80% - 95%, 85% - 95%, 90% - 95%, 70% - 90%, 75% - 90%, 80% - 90%, 85% - 90%, 70% - 85%, 75% - 85%, 80% - 85%, 70% - 80%, 75% - 80%, 70% - 75%, or 70%, 75%, 80%, 85%, 90%, or 95%.

[0085] In some embodiments, the second step of esterification with glycerol can be carried out at a temperature of about 17°C - 23°C. By way of non-limiting example, the esterification with glycerol can be carried out at 17°C - 23°C, 18°C - 23°C, 19°C - 23°C, 20°C - 23°C, 21°C - 23°C, 22°C - 23°C, 17°C - 22°C, 18°C - 22°C, 19°C - 22°C, 20°C - 22°C, 21°C - 22°C, 17°C - 21°C, 18°C - 21°C, 19°C - 21°C, 20°C - 21°C, 17°C - 20°C, 18°C - 20°C, 19°C - 20°C, 17°C - 19°C, 18°C - 19°C, 17°C - 18°C, or 17°C, 18°C, 19°C, 20°C, 21°C, 22°C, or 23°C.

[0086] In some embodiments, the second step of esterification with glycerol can be carried out for about 24 hours to 72 hours. By way of non-limiting example, the second step of esterification with glycerol can 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.

[0087] In some embodiments, the process of making a product enriched in MAG includes a third step of lipase inactivation and phase separation.

[0088] The product obtained from the above embodiments results in a processed oil having an MAG content of 40 wt% or more based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 40 wt% to about 99 wt% based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 50 wt% to about 99 wt% based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 60 wt% to about 99 wt% based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 70 wt% to about 99 wt% based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 80 wt% to about 99 wt% based on the total weight of the processed oil. In certain embodiments, the MAG content is from about 50 wt% to about 80 wt% based on the total weight of the processed oil. In any of the above embodiments, the TAG content is 5 wt% or less based on the total weight of the processed oil. In any of the above embodiments, the TAG content is 4 wt% or less, 3 wt% or less, 2 wt% or less, 1 wt% or less based on the total weight of the processed oil.

[0089] The products obtained from the above-described embodiments generally result in a processed oil that is substantially free of MCPD compounds. However, the starting oil may have more than 0.30 mg / kg of MCPD compounds and, in some cases, may have from about 1.0 mg / kg to about 12.00 mg / kg. More specifically, the processed oil obtained from the above method contains less than 100 mg / kg of MCPD and includes levels that are not detected by standard assays. As used herein, the term "substantially free" with respect to the amount of MCPD levels in the processed oil of the present invention means a level that is below the detection limit of the assay described in Example 11 below.

[0090] The products obtained from the above-described embodiments result in a processed oil that is enriched in MAG, specifically 1-MAG (MAG esterified at the sn-1 position). In the case of a processed oil made from a starting oil having an oleic acid content, this results in the production of 1-oleoyl monoacylglycerol (1-OG). Embodiments of the manufacturing process of the present disclosure have been found to be capable of efficiently converting even sn-2 oleic acid TAGs to 1-OG. For example, embodiments of the manufacturing process of the present disclosure starting from triolein can obtain three 1-OG molecules from a single triolein molecule, while in the digestion of triolein by pancreatic lipase, the lipase releases the oleic acid moieties at the sn-1 and sn-3 positions as free fatty acids, so that only one-third of the total oleic acid can be obtained in the form of monoacylglycerol (specifically, not 1-OG but 2-monoacylglycerol (2-OG)). Thus, the processed oil produced by the manufacturing method of the present disclosure can obtain a 1-OG content that is up to three times greater compared to normal digestion processes. The following reaction schematic shows the conversion of triolein to 2-OG and two free oleic acid molecules (Process A - normal digestion) and the conversion of triolein to three molecules of 1-OG (Process B) by the process of the present disclosure.

Chemical formula

[0091] Furthermore, it has also been found that in the manufacturing process embodiments of the present disclosure, the fatty acid profile of the starting oil in the processing oil can be preserved. Table 2 below shows the representative fatty acid profiles of various starting oils and provides the percentages of total fatty acid methyl esters (FAME). Nd - not determined. SAF - safflower, GRP - grape, SIL - milk thistle (Silynum marianum), HMP - hemp, SFL - sunflower, WHG - wheat germ, PMS - pumpkin seed, SES - sesame, RB - rice bran, ALM - almond, RPS - rapeseed (canola), PNT - peanut, OL - olive, COC - coconut, oils. Table 2 also provides the oleic acid / linoleic acid ratio and the oleic acid / linolenic acid ratio for each oil.

Table 2

[0092] In particular, linoleic acid (ω3 fatty acid) and linolenic acid (ω6 fatty acid) are known to be essential for humans and can be used in the production of longer-chain, more unsaturated fatty acids (otherwise known as long-chain polyunsaturated fatty acids (LC-PUFA)) including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).

[0093] In some embodiments, the product comprises the processing oil of the present disclosure. In some embodiments, the processing oil itself is a single product.

[0094] In some embodiments, the processing oil comprises an MAG content of 30 wt% or more of the total weight of the processing oil. By way of non-limiting example, the processing oil may have an MAG content of about 30% - 95%, 40% - 95%, 50% - 95%, 60% - 95%, 70% - 95%, 80% - 95%, 90% - 95%, 30% - 90%, 40% - 90%, 50% - 90%, 60% - 90%, 70% - 90%, 80% - 90%, 30% - 80%, 40% - 80%, 50% - 80%, 60% - 80%, 70% - 80%, 30% - 70%, 40% - 70%, 50% - 70%, 60% - 70%, 30% - 60%, 40% - 60%, 50% - 60%, 30% - 50%, 40% - 50%, or about 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% of the total weight of the processing oil.

[0095] In some embodiments, including the above embodiments regarding the MAG content, the processing oil comprises a DAG content of 5 wt% or more of the total weight of the processing oil. By way of non-limiting example, the processing oil may have a DAG content of about 5% - 66%, 10% - 66%, 20% - 66%, 30% - 66%, 40% - 66%, 50 - 66%, 5% - 50%, 10% - 50%, 20% - 50%, 30% - 50%, 40% - 50%, 5% - 40%, 10% - 40%, 20% - 40%, 30% - 40%, 5% - 30%, 10% - 30%, 20% - 30%, 5% - 20%, 10% - 20%, 5% - 10%, or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, or 66% of the total weight of the processing oil.

[0096] In some embodiments, including the above embodiments regarding the MAG and / or DAG content, the process oil comprises an FFA content of 5 wt% or more of the total weight of the process oil. By way of non-limiting example, the process oil may have an MAG content of about 5 wt% to 66 wt%, 10 wt% to 66 wt%, 20 wt% to 66 wt%, 30 wt% to 66 wt%, 40 wt% to 66 wt%, 50 to 66 wt%, 5 wt% to 50 wt%, 10 wt% to 50 wt%, 20 wt% to 50 wt%, 30 wt% to 50 wt%, 40 wt% to 50 wt%, 5 wt% to 40 wt%, 10 wt% to 40 wt%, 20 wt% to 40 wt%, 30 wt% to 40 wt%, 5 wt% to 30 wt%, 10 wt% to 30 wt%, 20 wt% to 30 wt%, 5 wt% to 20 wt%, 10 wt% to 20 wt%, 5 wt% to 15 wt%, 10 wt% to 15 wt%, 5 wt% to 10 wt%, or about 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, or 66 wt% of the total weight of the process oil.

[0097] In some embodiments, including the above embodiments regarding the MAG, DAG, and / or FFA content, the process oil does not contain TAG or comprises a TAG content of 5 wt% or less of the total weight of the process oil. By way of non-limiting example, the process oil may have a TAG content of about 0 wt% to 5 wt%, 1 wt% to 5 wt%, 2 wt% to 5 wt%, 3 wt% to 5 wt%, 4 wt% to 5 wt%, 0 wt% to 4 wt%, 1 wt% to 4 wt%, 2% to 4 wt%, 3 wt% to 4 wt%, 0 wt% to 3 wt%, 1 wt% to 3 wt%, 2 wt% to 3 wt%, 0 wt% to 2 wt%, 1 wt% to 2 wt%, 0 wt% to 1 wt%, or 0 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, or 5 wt% of the total weight of the process oil. As a further non-limiting example, the TAG content may be less than 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.1%.

[0098] In some embodiments, the processing oil comprises about 30 wt% to 80 wt% MAG, about 10 wt% to about 30 wt% DAG, about 0 wt% to about 5 wt% TAG, and about 5 wt% to about 60 wt% FFA, based on the total weight of the processing oil.

[0099] In any of the embodiments herein, the processing oil is derived from an oil source and contains non-oil components that are naturally present in the oil source, and thus no non-oil components are added to the processing oil. By way of non-limiting example, such non-oily components can include antioxidants such as tocopherols (including α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, or γ-tocotrienol), and other vitamins such as vitamin K and structurally similar 2-methyl-1,4-naphthoquinone(3-) derivatives. In some embodiments, the antioxidant is selected from natural (e.g., mixed tocopherols or ascorbic acid) and synthetic (e.g., butylated hydroxyanisole or butylated hydroxytoluene) antioxidants. Further examples of non-oil components include ceramide phosphate, monogalactosyldiacylglycerol, phosphatidylmethanol, sitosteryl ester, campesteryl ester, sphingolipids, phosphatidylglycerol, wax ester, and sphingomyelin.

[0100] In any of the embodiments of this specification, the processing oil contains monoglyceryl oleate (MOG) and has a total fatty acid content. MOG can contribute from about 5 wt% to about 75 wt% of the total fatty acid content of the processing oil. In some embodiments, by way of example and not limitation, MOG can contribute from about 10 wt% to about 75 wt%, from about 20 wt% to about 75 wt%, from about 30 wt% to about 75 wt%, from about 40 wt% to about 75 wt%, from about 50 wt% to about 75 wt%, or from about 60 wt% to about 75 wt% of the total fatty acid content of the processing oil. In some embodiments, the processing oil contains oleic acid in amounts of about 5 wt% and about 75 wt% of the total fatty acid content of the processing oil. In some embodiments, by way of example and not limitation, oleic acid can contribute from about 10 wt% to about 75 wt%, from about 20 wt% to about 75 wt%, from about 30 wt% to about 75 wt%, from about 40 wt% to about 75 wt%, from about 50 wt% to about 75 wt%, or from about 60 wt% to about 75 wt% of the total fatty acid content of the processing oil.

[0101] In any of the embodiments of this specification, the processing oil contains MOG, and MOG contains at least 50 wt% 1-oleoyl monoglyceride (1-OG) of the total amount of MOG. By way of example and not limitation, the processing oil can contain 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 of the total amount of MOG.

[0102] In any of the embodiments of this specification, the processing oil contains oleic acid in an amount of about 10 wt% to about 75 wt% of the total fatty acid content of the processing oil. By way of example and not limitation, oleic acid can be present in an amount of about 10 wt% to about 75 wt%, about 20 wt% to about 75 wt%, about 30 wt% to about 75 wt%, about 40 wt% to about 75 wt%, about 50 wt% to about 75 wt%, about 60 wt% to about 75 wt%, about 10 wt% to about 20 wt%, about 10 wt% to about 30 wt%, about 10 wt% to about 40 wt%, about 10 wt% to about 50 wt%, or about 10 wt% to about 60 wt% of the total fatty acid content of the processing oil. In any of the embodiments of this specification, oleic acid is esterified at the sn-1 position. By way of example and not limitation, the processing oil can contain 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 the total amount of oleic acid esterified at the sn-1 position.

[0103] In any of the embodiments of this specification, the processing oil contains linoleic acid in an amount of about 1.5 wt% to about 90 wt% of the total fatty acid content of the processing oil. By way of example and not limitation, linoleic acid can be present in an amount of about 10 wt% to about 90 wt%, about 20 wt% to about 90 wt%, about 30 wt% to about 90 wt%, about 40 wt% to about 90 wt%, about 50 wt% to about 90 wt%, about 60 wt% to about 90 wt%, about 70 wt% to about 90 wt%, about 80 wt% to about 90 wt%, about 10 wt% to about 25 wt%, or about 10 wt% to about 20 wt% of the total fatty acid content of the processing oil. In some embodiments, the processing oil contains oleic acid and linoleic acid, and the ratio of oleic acid:linoleic acid is about 0.01 to 5. By way of example and not limitation, the ratio of oleic acid:linoleic acid can be 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.

[0104] In any of the embodiments of this specification, the processing oil contains linolenic acid in an amount of about 0.01 wt% to about 2 wt% of the total fatty acid content of the processing oil. By way of non-limiting example, linolenic acid can be present in an amount of about 0.1 to about 2 wt%, about 0.5 to about 2 wt%, about 1% to about 2 wt%, or about 1.5 wt% to about 2 wt% of the total fatty acid content of the processing oil. In some embodiments, the processing oil contains oleic acid and linolenic acid, and the ratio of oleic acid to linolenic acid is about 1 to about 100. By way of non-limiting example, the ratio of oleic acid:linolenic acid can be about 10 to about 100, about 20 to about 100, about 30 to about 100, about 40 to about 100, about 50 to about 100, about 60 to 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. It should be understood that references to fatty acids in the claims are not to be construed as limited to free fatty acids only and can refer to fatty acids in glyceride form. In the processing oils of the present disclosure, the fatty acids are primarily in MAG form, and in the pre-processing oils, they are primarily in TAG form. In certain cases, to a lesser extent, the fatty acids may be in free or DAG form. In the processing oil, the free fatty acids are typically less than 10%.

[0105] In any of the embodiments of this specification, the processing oil has a fatty acid profile that is substantially the same as the fatty acid profile of the pre-processing oil from which the processing oil is produced. By way of non-limiting example, the fatty acid profile of the processing 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. In some embodiments, the fatty acid profile contains oleic acid, linoleic acid, and linolenic acid. However, any combination of fatty acids can form the fatty acid profile. By way of non-limiting example, the fatty acid profile can contain the fatty acids listed in Table 2, as well as any combination of EPA and DHA.

[0106] In any of the embodiments of this specification, the processed oil contains three times the amount of MAG molecules compared to the number of TAG molecules in the pre-processed oil before the oil is produced. For example, on a molar basis, the amount of oleic acid in the form of MAG in the processed oil can be up to three times the amount of oleic acid in the TAG in the pre-processed oil. By way of non-limiting example, 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 TAG in the pre-processed oil. For example, each oleic acid moiety in the form of TAG in the pre-processed oil can be converted to oleic acid MAG, such that, for example, up to three oleic acid moieties, such as in triolein, are converted to three oleic acid MAGs. In some embodiments, the amount of MAG in the processed oil is three times the amount of TAG in the pre-processed oil before the processed oil is produced. For example, the number of MAGs produced corresponds to approximately three times the number of TAGs in the pre-processed oil. In some embodiments, the processed oil contains oleic acid in the form of oleic acid monoglyceride in an amount substantially the same as the amount of oleic acid in the pre-processed oil before the processed oil is produced.

[0107] In some embodiments, the product or food can contain at least 1% MAG. By way of non-limiting example, the food can contain at least 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt% or more, or any range or amount therebetween of MAG in the product or food. As a further non-limiting example, the product or food can contain 5 wt% to 15 wt% MAG of the total weight of the product or food.

[0108] In some embodiments, the product or food may contain at least 3% by weight of any of the processing oils of the embodiments herein, based on the total weight of the product or food. By way of non-limiting example, the food may contain 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% by weight or more of any of the processing oils of the embodiments herein, and any range or amount therebetween, of the product or food.

[0109] In some embodiments, the food may further comprise a carbohydrate source. By way of non-limiting example, such carbohydrate source may include monosaccharides such as glucose and fructose, derived from carbohydrate sources such as fruits and agave syrup. Other carbohydrate sources include other plant-based liquid sugars, starches, and sugar alcohols.

[0110] In some embodiments, the food may further comprise a protein source. In certain aspects, the protein source may be hydrolyzable or partially hydrolyzable. By way of example and not limitation, such protein sources can include milk proteins (casein and whey), as well as other plant proteins including those from soy, rice and rice bran, lentils, chickpeas, peanuts, almonds, spirulina (algae), quinoa, mycoprotein, chia seeds and flax seeds. The hydrolyzed protein may be highly hydrolyzed, and the legume protein is enriched in peptides 1 - 10 amino acids in length. In some embodiments, the protein is enriched in peptides 1 - 10 amino acids in length by about 25% - 75% compared to commercially available partially hydrolyzed proteins and peptames and other whey-based hydrolysis products such as Crucial. By way of example and not limitation, the protein is enriched in peptides 1 - 10 amino acids in length by at least 25% - 75%, 35% - 75%, 45% - 75%, 55% - 75%, 65% - 75%, 25% - 65%, 35% - 65%, 45% - 65%, 55% - 65%, 25% - 55%, 35% - 55%, 45% - 55%, 25% - 45%, 35% - 45%, 25% - 35%, or 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or 75%.

[0111] In some embodiments, the food can be liquid, semi-solid or solid. By way of example and not limitation, semi-solids can include products such as puddings, mousses, pops, or ice cream. By way of example and not limitation, liquids can be shakes or other drinks. By way of example and not limitation, solids can be bars or other solid foods.

[0112] In some embodiments, the product or food further comprises a viscosity modifier. The viscosity modifier can be, by way of example but not limited to, xanthan gum or acacia gum. In some embodiments, the product or food can further comprise components that improve structure or stability, such as, by way of example but not limited to, gum arabic, sunflower lecithin, and xanthan gum. In some embodiments, the product or food further comprises a fiber source such as, by way of example but not limited to, oligosaccharides. In some embodiments, the product or food can further comprise a food preservative such as, by way of example but not limited to, sodium benzoate or potassium sorbate.

[0113] In some embodiments, the product or food further comprises a flavor, masker, or blocker. By way of example but not limited to, the flavor can include chocolate, vanilla, strawberry, or other flavors.

[0114] In some embodiments, the food product has a total weight of at least 25 grams. By way of non-limiting example, 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 of from about 25 grams to about 3000 grams. By way of non-limiting example, the food product can have a weight of from 25 grams to 3000 grams, from 25 grams to 2500 grams, from 25 grams to 2000 grams, from 25 to 1000 grams, from 25 grams to 500 grams, from 50 grams to 3000 grams, from 50 grams to 2500 grams, from 50 grams to 2000 grams, from 50 grams to 1500 grams, from 50 grams to 1000 grams, from 50 grams to 500 grams, from 100 grams to 3000 grams, from 100 grams to 2500 grams, from 100 grams to 2000 grams, from 100 grams to 1500 grams, from 100 grams to 1000 grams, from 100 grams to 500 grams, from 250 grams to 3000 grams, from 250 grams to 2500 grams, from 250 grams to 2000 grams, from 250 grams to 1500 grams, from 250 grams to 1000 grams, from 250 grams to 500 grams, from 500 grams to 3000 grams, from 500 grams to 2500 grams, from 500 grams to 2000 grams, from 500 grams to 1500 grams, from 500 grams to 1000 grams, from 1000 grams to 3000 grams, from 1000 grams to 2500 grams, from 1000 grams to 2000 grams, from 1000 grams to 1500 grams, from 1500 grams to 3000 grams, from 1500 grams to 3000 grams, from 2000 grams to 3000 grams, from 2000 grams to 2500 grams, from 25 grams to 250 grams, from 50 grams to 250 grams, from 100 grams to 250 grams, from 25 grams to 100 grams, from 50 grams to 100 grams, from 25 grams to 50 grams, or a total weight of 25 grams, 50 grams, 100 grams, 150 grams, 200 grams, 250 grams, 300 grams, 350 grams, 400 grams, 450 grams, 500 grams, 1000 grams, 1500 grams, 2000 grams, 2500 grams, or 3000 grams or less.

[0115] In some embodiments, the food has a total calorie content of about 200 kcal to 1000 kcal. By way of example and not limitation, the food can have a calorie content of about 200 kcal to 1000 kcal, 400 kcal to 1000 kcal, 600 kcal to 1000 kcal, 800 kcal to 1000 kcal, 200 kcal to 800 kcal, 400 kcal to 800 kcal, 600 kcal to 800 kcal, 200 kcal to 600 kcal, 400 kcal to 600 kcal, 200 kcal to 400 kcal, or 200 kcal, 300 kcal, 400 kcal, 500 kcal, 600 kcal, 700 kcal, 800 kcal, 900 kcal, or 1000 kcal or less.

[0116] In some embodiments, about 20% to 75% of the calories in the food are derived from oil or fat. In one aspect, the oil or fat is any of the processed oils of the embodiments herein. In yet another aspect, the processed oil has an MAG content of 30 wt% or more of the total weight of the processed oil. In other aspects, the processed oil has an MAG content of about 40 wt% to about 99 wt% of the total weight of the processed oil. In yet another aspect, the processed oil has a TAG content of less than 5 wt% of the total weight of the processed oil. By way of non-limiting example, 20% to 50%, 30% to 50%, 40% to 50%, 20% to 40%, 30% to 40%, 20% to 30%, 20% to 75%, 30% to 75%, 40% to 75%, 50% to 75%, 60% to 75%, 70% to 75%, 20% to 70%, 30% to 70%, 40% to 70%, 50% to 70%, 60% to 70%, 20% to 60%, 30% to 60%, 40% to 60%, 50% to 60%, or about 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, or 75% of the calories of the food are derived from any of the processed oils described above.

[0117] In any of the above embodiments of the food, about 20% to 50% of the calories of the food are derived from a carbohydrate source. By way of non-limiting example, 20% to 50%, 30% to 50%, 40% to 50%, 20% to 40%, 30% to 40%, 20% to 30%, or about 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, or 50% of the calories of the food are derived from a carbohydrate source.

[0118] In any of the above-described embodiments regarding food, about 10% to 50% of the calories of the food are derived from the protein source. Without limitation, by way of example, 10% to 50%, 20% to 50%, 30% to 50%, 40% to 50%, 10% to 40%, 20% to 40%, 30% to 40%, 10% to 30%, 20% to 30%, 10% to 20%, or about 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, or 50% of the calories of the food are derived from the protein source.

[0119] It should be understood that the embodiments disclosed above for food can be combined.

[0120] In some embodiments, the food of the present disclosure comprises the processed oil of the present disclosure.

[0121] In some embodiments, the EMO-based product is consumed by an individual having a dysfunctional digestive system, including, without limitation, by way of example, an individual suffering from EPI, or an individual utilizing PERT with food. In some embodiments, the EMO-based product is consumed by an individual desiring a faster or more complete conversion of lipids to serum triglycerides. Accordingly, a method for feeding a human or animal subject having a dysfunctional digestive system is provided. The method includes administering to the patient a food according to any of the above-described embodiments, or a combination of such embodiments. In one aspect, the human or animal subject suffers from EPI. In another aspect, the human or animal subject suffers from cystic fibrosis, pancreatitis, pancreatic cancer, or biliary stasis.

[0122] In some embodiments, a method for promoting glucose homeostasis in a subject in need thereof is provided, comprising administering to the subject a composition comprising the processed oil of the present disclosure. In some embodiments, the subject suffers from a condition that affects glucose homeostasis. In some embodiments, the condition is insulin resistance or diabetes. In some embodiments, the condition is type II diabetes.

[0123] In some embodiments, a method for treating a subject in need of treatment for diabetes is provided, comprising administering to the subject a composition comprising the processed oil of the present disclosure. In some embodiments, the diabetes is type II diabetes.

Examples

[0124] Example 1: A process for producing a product enriched in MAG compared to a starting oil rich in TAG. The method for producing a product enriched in MAG compared to a starting oil rich in TAG involves three important steps. (1) Mild enzymatic reaction: sequentially hydrolyzing triglycerides (TAG) to convert natural oil into a specific combination of FFA, MAG, DAG, and low-residual TAG, (2) Esterification with glycerol: mainly producing a large amount of MAG and leaving a low concentration of FFA, and (3) Isolation of the modified lipid product: which is achieved by phase separation, with or without the aid of centrifugation.

[0125] Step 1. Enzymatic conversion of triacylglycerol Preparation of buffer. A sodium citrate solution (100 mM, pH 5.8) was prepared in a stirred tank reactor. 11.1 L of deionized (DI) water was placed in a mixing vessel, the stirrer was set at 200 RPM, and 0.213 kg of citric acid (anhydrous) was added. After dissolving the powder, the pH was adjusted to pH = 5.8 with sodium hydroxide solution (about 0.121 kg). 220 mL was removed for subsequent enzyme preparation.

[0126] Preparation of enzyme solution. The enzyme solution was prepared in another 250 mL bottle with gentle stirring. 200 mL of citrate buffer was placed in a mixing container. 10 g of AMANO lipase AY was added and the bottle was shaken until the enzyme was dissolved.

[0127] Conversion of triglyceride oil mixture. Three vegetable oils, olive oil, linseed oil and sunflower seed oil were added to a container to obtain a total of 10 kg of vegetable oil mixture. Vacuum was applied to reduce the pressure to about 20 mmHg to degas the material (especially from any dissolved oxygen). Stirring was set at 200 RPM, the mixture was heated to 33 °C and stirred for about 15 minutes to remove any dissolved gas. Then the vacuum was replaced with a nitrogen gas atmosphere. Once the mixture was well dispersed, the enzyme preparation in 220 mL of buffer was added. Stirring was continued and the reaction was monitored for 24 hours until the conversion to FFA was complete based on TLC analysis.

[0128] The reactor temperature was raised to 70 °C, stirring was restarted and the enzyme was inactivated for 1 hour.

[0129] Stirring was stopped and the phases were separated for about 60 minutes.

[0130] To ensure removal of residual protein at the interface, the aqueous phase (lower phase) was removed along with a small amount of the oil phase.

[0131] Step 2. Esterification with glycerol. Typically, re-esterifying FFA with glycerol produces a mixture of MAG, DAG and TAG. It was found that by significantly reducing the temperature (below 25 °C) and removing the water formed during the reaction (by evaporation), the proportion of MAG in the product could be highly concentrated (at least 60% but up to 95%). This was unexpected.

[0132] In this reaction, the reaction product from step 1 (about 10 L) was cooled to about 30 °C and stirred at 300 RPM. 10 kg of food-grade glycerol was added to the lipid mixture, and the temperature was maintained at about 30 °C. The mixture was stirred to produce a dispersion of oil and glycerol. A vacuum was applied to dry the reaction mixture. First, a vacuum (25 mmHg, Torr) was applied, and water was recovered in a receiver at a predetermined position. When the evaporation of the residual water stopped, 20 g of Amano lipase G dissolved in water (50 mL) was added to the reactor. The temperature was lowered to 23 °C, and using an oil diaphragm pump and a cold trap, the vacuum was changed to 5 mmHg to recover water. This mixture was stirred at 300 RPM under vacuum at 23 °C for 72 hours. At this point, the vacuum was broken, and the mixture was covered with nitrogen gas. Using TLC, the mixture was analyzed after 72 hours, and as shown in Figure 1, the conversion to MAG was evaluated.

[0133] Step 3. Lipase inactivation and phase separation. After the reaction was completed, the lipase was inactivated by heating the mixture to 70 °C for 1 hour (under nitrogen gas coating). At this point, the MAG oil and glycerol were well mixed, and it was very difficult to separate them by conventional gravity or centrifugation methods. After conducting a significant amount of experiments, it was found that by adding 0.3 wt% of salt (NaCl) to the reaction mixture under stirring, the lipid could be separated from the excess glycerol. The resulting mixture was then cooled to about 60 °C and left standing without stirring for about 1 hour.

[0134] The lipid oil phase was separated from the remaining heavier glycerol phase. The glycerol phase was removed. This contained some salt, residual water, and the dissolved inactivated enzyme (contained in the visible interface). The glycerol phase can be reused after membrane filtration and needs to be stored for recycling. Tocopherol (vitamin E) was added to obtain a product oil with a concentration of 200 ppm (0.02 wt%). The hydrolyzed oil (about 10 kg) can be used immediately and can be stored under nitrogen coating.

[0135] Storage of the product. The final hydrolysis product was transferred to a food-grade container with a nitrogen gas overlay for storage and transportation.

[0136] Example 2: Characterization of the oil produced in Example 1 The reaction products and the overall process can be evaluated using thin-layer chromatography and gas chromatography.

[0137] Thin-layer chromatography test. The components of the oil sample were separated using a TLC plate (Analtech Uniplate Silica Gel GHL, 20×20 cm, 250 μm, containing an inorganic binder). The solvent was a hexane:diethyl ether:acetic acid (70:30:1) solution. A typical sample size was 3 μL. After the solvent front had moved near the top of the plate (about 1 cm), the plate was removed from the TLC tank and the solvent was evaporated in a draft. The components were visualized in the TLC tank with iodine vapor (at room temperature), and the relative intensities were estimated by colorimetric imaging (Amersham 600 Imager). After 15 minutes in the tank, the plate was removed and photographed. After 30 - 60 minutes, the intensity of the spots decreased.

[0138] Physical properties were determined to establish the consistency, color, water content, fat, and oil (miscibility) of the product.

[0139] Figure 1 shows the final results of Steps 1 - 3 in the process of producing a product enriched in MAG compared to the starting TAG-rich oil, as described in Example 1. Figure 2 shows that the tocopherols initially present in the olive oil are preserved after the steps described in Example 1. In Figure 2, it can be seen that the tocopherol spots track above the TAG spots in all three lanes.

[0140] Fatty Acid Profile Test - Gas Chromatography. The lipid components included C10:0 capric acid, C12:0 lauric acid, C14:0 myristic acid, C16:0 palmitic acid, C18:0 stearic acid, C18:1 oleic acid, C18:2 linoleic acid, and C18:3 α-linolenic acid, which were analyzed after derivatization as fatty acid methyl esters and compared to standards. For derivatization, the sample (500 μl) was added to a 5 ml reaction tube containing 2 ml of boron trifluoride solution (12% in methanol), 20 μl of dimethoxypropane, and 100 μl of tridecane acid internal standard solution (10 mg / ml). The reaction tube was vortexed and incubated in a heat block at 60 °C for 30 minutes.

[0141] The reaction tube was removed from the heat block and cooled 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 separated for 3 minutes. The upper (hydrophobic) phase was transferred to a 1.5 ml tube containing approximately 50 mg of sodium sulfate (anhydrous). After vortexing for 60 seconds, the 1.5 ml tube was centrifuged and approximately 500 μl of the clarified dry hydrophobic phase was transferred to a gas chromatography sample vial.

[0142] The samples were analyzed using an Agilent 7890A gas chromatograph with a flame ionization detector and Agilent Openlab CDS Chemstation software. GC column: Omegawax 100 (15 m × 0.1 mm × 0.1 μm) column. The results were converted to weight % by internal standard reference.

[0143] Figure 3 shows the distribution of FFA, MAG, DAG, and TAG in the Ensure and GBFS products of the present disclosure. The % of FFA, MAG, DAG, and TAG in the oil determined by thin layer chromatography.

[0144] Example 3: Another example of a process for making a product enriched in MAG compared to a TAG-rich starting oil. The following procedure is shown by the block diagram of FIG. 4.

[0145] Vegetable 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 degas and remove oxygen. Lipase AY was added. The hydrolysis of the mixture was carried out at a temperature of 33 °C + / - 2 °C for 14 to 24 hours under a nitrogen blanket.

[0146] The lipase was inactivated at a temperature of 70 °C + / - 2 °C for 1 hour. The aqueous phase containing the inactivated enzyme was drained. Glycerol was added. The reaction product was then cooled to 22 °C + / - 2 °C. Then, Lipase G was added and water was evaporated under a moderate vacuum.

[0147] Re-esterification was carried out at a temperature of 20 °C + / - 2 °C for 72 hours under a high vacuum (about 720 mmHg). Lipase G was inactivated at 70 °C + / - 2 °C for 1 hour and salts were added to the reaction product.

[0148] Enzyme inactivation and phase separation were carried out at 70 °C + / - 2 °C for 1 hour under a nitrogen blanket. The aqueous phase containing the inactivated enzyme, glycerol, and salts was drained. The reaction was cooled to 60 °C + / - 2 °C. An antioxidant was added. The final product was stored at 4 °C + / - 2 °C under nitrogen.

[0149] Example 4: Ready-to-Drink Formulation Incorporating MAG and Hydrolyzed Protein The products of the present disclosure were manufactured as a conventional "milkshake" formulation containing a fat source, a protein source, a carbohydrate source, a vitamin source, and a fiber source, in addition to the conventional surfactants and stabilizers typically found in these products. Individual servings were 250 ml. The ingredients listed on the ingredient label were as follows. Water, organic agave syrup, hydrolyzed soy 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, calcium D-pantothenate, pyridoxine hydrochloride, thiamine hydrochloride, riboflavin, vitamin D3, folic acid, cyanocobalamin, vitamin K2.

[0150] Carbohydrates were supplied as monosaccharides (glucose and fructose) from fruits and agave syrup.

[0151] The protein in the product was a partially hydrolyzed soy protein (PURIS Pea Protein 870H, World Food Processing LLC, Turtle Lake, WI 54889).

[0152] The inventors also produced a highly hydrolyzed soy protein (EHP) containing peptides in a more biologically available size range for cross-membrane transport across the intestinal wall. EHP was produced by further enzymatic hydrolysis. For example, a partially hydrolyzed soy protein (Puris Pea Protein 870H described above) protein was dissolved at a concentration of 25 mg / ml in 100 mM phosphate buffer. Enzyme was added and the reaction was incubated overnight at 50°. Three different commercially available GRAS enzymes were evaluated. Alcalase, Thermoase, Flavorzyme.

[0153] The average size and distribution of peptides in the protein sample were evaluated using size exclusion chromatography. The sample was dissolved in 100 mM phosphate buffer (pH 6.8) at a concentration of 25 mg / ml and analyzed on a Shimadzu HPLC equipped with a UV detector (214 nm) using a Phenomenex Yarra 3um SEC-2000 column (eluted with 100 mM sodium phosphate buffer (pH 6.8) at a flow rate of 0.8 mL / min at room temperature). The sample was compared to a molecular weight standard (Phenomenex SEC standard part ALO-3042). Sizes were estimated using a calibration curve generated from known molecular weight standards. The average size of the non-hydrolyzed legume protein was approximately 200 amino acids. The average size of the Puris Pea 870H partially hydrolyzed product was 34 amino acids, with a significant amount in the 2 - 40 amino acid range, similar to other (whey-based) protein hydrolysates.

[0154] Figure 5 shows the distribution of amino acids and peptides in ready-to-drink beverage nutritional drinks (as reported in E. Phillips et al., 2005 Peptide-Based Formulas: the Nutraceuticals of Enteral Feeding? EPCN October: 40 - 45) compared to the GBFS hydrolyzed legume protein described above. Figure 5 shows the percentage of amino acid sizes (Y-axis) (1 amino acid, 2 - 4 amino acids, 9 - 10 amino acids, 10 - 40 amino acids, or more 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, mainly 1 - 7 amino acids.

[0155] Fats are provided in the form of reconstituted lipid MAG and are manufactured from a blend of olive oil (70%), sunflower oil (21%) and linseed oil (9%) to provide the energy and other benefits of polyunsaturated fatty acids (PUFA), ω6 PUFA, and ω3 PUFA. The ratio of ω6 to ω3 is approximately 4:1.

[0156] Arabic gum, sunflower lecithin, and xanthan gum are common GRAS food ingredients used to provide structure and stability to the drink. Oligosaccharides provide non-digestible fiber. Potassium sorbate and sodium benzoate are common food preservatives. Instant coffee and vanilla provide flavor.

[0157] A vitamin package containing fat-soluble vitamins and water-soluble vitamins was included.

[0158] The nutrition label of the prototype product is shown in Table 3. In Table 3, the **percent daily value (DV%) is based on a 2,000-calorie diet. †The daily value (DV) has not been established.

Table 3

[0159] Sensory evaluation. FFA generated from the vegetable oil blend was found to be off-tasting by the taste panel. Surprisingly, the MAG oil generated from this blend had a good mouthfeel and was similar in taste and texture to the original triglyceride oil. When the MAG oil was formulated into the RTDS product described above, its flavor was acceptable and indistinguishable from similar commercial products having intact (undigested) lipids and proteins.

[0160] Example 5: Production of Multiple Batches of EMO The timing of the process described in Example 1 for manufacturing EMO was evaluated to produce an oil having a MAG content of greater than 70%, a MAG + FFA content of greater than 85%, and a TAG content of 5% or less.

[0161] Table 4 shows a scan of a TLC plate showing the concentrations of MAG and FFA in enzymatically modified EMO generated from a blend of olive oil / linseed oil / sunflower oil (7:2:1 ratio). In these experiments, step 2 was extended to 84 hours to establish the upper limits of timing and temperature to avoid TAG formation. [Table 4]

[0162] This reaction can be monitored substantially in real time by TLC analysis and stopped at any point during step 2 to obtain the desired amounts of MAG, DAG, TAG, and FFA. It has been found that 72 hours of reaction time for step 2 is a practical and productive stopping point, as illustrated in Example 6.

[0163] Example 6: Evaluation of TAG-free enzymatically modified almond oil by NMR analysis. TAG-free EMO was generated using almond oil. The reaction conditions were as described in Example 1. Step 2 was 72 hours, minimizing TAG formation.

[0164] Figures 6A - 6B show the 13 13C-NMR analysis of EMO generated from almond oil. Figure 6A shows the 13 13C-NMR signals associated with standard TAG (tristearin), and characteristic peaks at 62.173 ppm and 68.921 ppm. Figure 6B shows the 13 13C-NMR signals of the EMO. It shows the absence of distinguishable TAG signals. The integral values of the actual signals indicate that the acylglycerol distribution between MAG:DAG is 88%:12%. Samples were analyzed on a JEOL model ECA600II NMR spectrometer operating at 600 MHz protons and 150 MHz carbon. Samples were prepared in 5 mm tubes and run at ambient temperature, locked with CDCl3.

[0165] Example 7: Clinical trial of an EMO-based ready-to-drink shake The test was designed to show that patients with EPI can consume the TAG-free oil-produced food manufactured by the inventors without taking enzyme supplements, absorb lipids in the serum, and still produce TAG.

[0166] The clinical trial was a single-site, randomized, double-blind, crossover study that evaluated 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").

[0167] The inclusion criteria for the trial were as follows: 1. Provision of a signed and dated informed consent form. 2. Demonstration of the willingness to comply with all trial procedures and availability during the trial period. 3. Male or female, 12 years of age or older. 4. Diagnosis of CF. 5. Currently receiving treatment with a commercially available pancreatic enzyme product for at least 3 months. 6. Clinically stable condition without evidence of acute respiratory disease within 1 month of enrollment. 7. Stable body weight (defined as not having lost more than 5% within 3 months of enrollment). 8. Women of childbearing potential must agree to continue using a medically acceptable method of contraception throughout the trial and for 30 days after the last dose of the investigational product. Medically acceptable methods of contraception include bilateral tubal ligation or contraceptive implant, contraceptive injection (Depo-Provera (trademark)), intrauterine device, or oral contraceptives taken within the past 3 months (if the subject agrees to continue using them during the study), or another method of contraceptive control, or the use of a double-barrier method consisting of any combination of two of the following: pessary, cervical cap, condom, or spermicide. 9. Ability to take oral medications and oral liquid nutritional supplements, and willingness to comply with the trial intervention. 10. Agreement to comply with lifestyle considerations (see Section 5.3) during the trial period.

[0168] The exclusion criteria for the clinical trial included the following: 1. Evidence of cardiovascular, respiratory (excluding underlying diseases), urogenital, gastrointestinal / liver (excluding underlying diseases), hematological / immunological, head, ear, eye, nose, throat, dermatological / connective tissue, musculoskeletal, metabolic / nutritional (excluding underlying diseases), endocrine (excluding diabetes under management), neurological / psychiatric, allergy (to milk, nuts, or soy), recent major surgery, or other related diseases (revealed by medical history, physical examination, and / or clinical tests) that may limit participation in or completion of the study. 2. History of acute abdomen in the past year. 3. History of fibrotic colon disease. 4. History of distal intestinal obstruction syndrome (DIOS) within 6 months before registration. 5. Solid organ transplantation or surgery affecting the large intestine other than appendectomy. 6. Small intestine surgery that significantly affects absorption ability (e.g., gastrectomy or pancreatectomy). 7. Inflammatory bowel disease including chronic diarrhea diseases not related to pancreatic insufficiency. 8. Celiac disease or Crohn's disease. 9. Receiving enteral tube nutrition for more than 50% of daily calorie intake. 10. Pregnant or lactating. 11. Any type of malignancy involving the digestive tract in the past 5 years. 12. Known allergy to the inactive ingredients (excipients) of pancreatin or pancreatin capsules. 13. Suspicion of non-compliance or non-cooperation. 14. Intake of investigational drug within 30 days before the start of the clinical trial. 15. Mental disorders or any other lack of suitability in the investigator's findings that exclude the subject's ability to participate in or complete the trial. 16. Diagnosis of human immunodeficiency virus in the medical history. 17. Lung transplantation or other solid organ transplantation, or description of a forced expiratory volume (FEV) of 25% or less. 18. Use of lipid-lowering therapies, including statins, fibrates, niacin, and proprotein convertase subtilisin / kexin type 9 (PCSK9) inhibitors, that cannot be taken from at least 14 days prior to Day 1 of the trial through Day 15 of the trial. Patients were male or female 12 years of age and older with a diagnosis of cystic fibrosis. Patients were also currently receiving treatment with a commercially available pancreatic enzyme product for at least 3 months and were in a clinically stable condition without evidence of acute respiratory disease within 1 month of enrollment.

[0169] Patients visited the clinic after an overnight fast and a standardized dinner. Patients in Arm 1 (10 patients) were administered RTDS along with PERT placebo, and patients in Arm 2 (10 patients) were administered a standard nutritional supplement with PERT. Serial blood samples (0, 1, 2, 3, 4, 5, 6 hours) over 6 hours were obtained from patients in both study arms without repeated administration of RTDS or the standard nutritional supplement. Water consumption was allowed during the study.

[0170] Patients returned to the clinic for Treatment 2 (crossover treatment) after an overnight fast and a standardized evening meal. Patients in Arm 1 were administered a standard nutritional supplement with PERT, and patients in Arm 2 were administered RTDS along with PERT placebo. Serial blood samples (0, 1, 2, 3, 4, 5, 6 hours) over 6 hours were obtained from patients in both study arms without repeated administration of RTDS or the standard nutritional supplement.

[0171] Standard nutritional supplements contained the following: water, glucose syrup, sugar, vegetable oils (canola, high oleic sunflower, corn), milk protein concentrate, and less than 2% soy protein isolate, calcium caseinate, sodium caseinate, acacia gum, fructooligosaccharides, inulin (from chicory), soy lecithin, salt, natural and artificial flavors, carrageenan potassium citrate, calcium phosphate, magnesium phosphate, magnesium chloride, sodium ascorbate, choline bitartrate, DL-α-tocopheryl acetate, ascorbic acid, potassium chloride, ferrous sulfate, zinc sulfate, niacinamide, calcium pantothenate, manganese sulfate, copper sulfate, pyridoxine hydrochloride, thiamine hydrochloride, β-carotene, vitamin A palmitate, riboflavin, folic acid, chromium chloride, biotin, potassium iodide, phylloquinone, sodium selenite, sodium molybdate, vitamin D3, vitamin B12.

[0172] RTDs contained the following: water, organic date syrup, enzyme-modified almond oil, enzyme-hydrolyzed soy protein, soluble corn fiber, cocoa powder, natural flavor, salt, vitamin C, vitamin E (dl-α-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 K1, vitamin D3 (cholecalciferol), biotin, vitamin B12 (cyanocobalamin).

[0173] The nutritional supplement was 5.9% fat, 5.9% protein, and 19% carbohydrates, and the RTD was 7.4% fat, 4.7% protein, and 9.8% carbohydrates.

[0174] The lipid dosage was 0.5 g / kg body weight. The lipids in the standard nutritional supplement were a blend of TAGs derived from canola oil, high-oleic sunflower oil, and corn oil. In the intervention drink, MAG was produced from almond oil. The lipid dosage for each patient was based on a well-established "lipid load test", which is similar to the glucose load test with a well-known design and scope. 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 then hourly for 6 hours. Serum triglyceride levels were measured using standard laboratory methods.

[0175] The PERT dosage used in this study followed the dosage guidelines recommended by the manufacturer (2,500 IU of lipase activity per gram of fat ingested), which corresponded to 3 - 4 capsules during the crossover phase of the study.

[0176] Figure 7 shows the increase in serum triglycerides after ingestion of an EMO-based ready-to-drink shake in two patients. In Figure 7, the dashed line represents the patient who received 0.5 g of enzyme-modified almond oil per kg of body weight, and the solid line represents the patient who received 0.5 g of canola oil, high-oleic sunflower oil, and corn oil per kg of body weight. These were incorporated into the RTDS and consumed over half an hour. Figure 7 shows that the enzyme-modified oil in the RTDS was absorbed by the patients and converted to serum triglycerides.

[0177] Figure 8 shows the increase in serum triglycerides in another patient after ingestion of the test drink. In Figure 8, the dashed line represents the serum triglycerides after ingestion of a MAG-based RTDS without PERT, and the solid line represents the standard care RTDS with PERT. The patient received either 0.5 g of enzyme-modified almond oil per kg of body weight or 0.5 g of corn oil per kg of body weight. These were incorporated into the RTDS and consumed over half an hour.

[0178] In this patient, lipid absorption and conversion to serum triglycerides were significantly faster after ingestion of MAG-based RTDS not relying on PERT than after ingestion of TAG-based (standard care) products relying on PERT. This suggests that the patient not only suffered from biliary stasis (disruption of bile flow from the liver) in addition to EPI and lacked sufficient enzymes, so that the canola oil, high-oleic acid sunflower oil, and corn oil in the standard care drink could not be properly emulsified. For pancreatic lipase to generate the surface area required for hydrolysis of oil into MAG and FFA transported to enterocytes, the oil needs to be emulsified into very small droplets. This activity requires bile acids derived from the liver. Since the TAGs in the standard of care drink could not be emulsified into the microemulsions required for optimal lipase activity in the small intestine, serum triglycerides did not increase as rapidly as the MAG formulation that does not require lipase activity.

[0179] The actual lipid dosage per patient was the same in all cases. 0.5 g / kg body weight.

[0180] The hypothetical glucose intake of a 65 kg patient in the clinical trial for standard nutritional supplements and RTDS is shown in Table 5 below. Most of the sugars and carbohydrates in the control drink are starch or amylose and are easily converted to glucose. In the test drink, the amount of drink that a hypothetical 65 kg patient would consume is small (the test drink has a high lipid concentration), and the carbohydrates are supplied in a smaller amount as a 50:50 mixture of fructose and glucose. Therefore, the actual glucose consumed is small.

Table 5

[0181] Figure 9 shows the increase in serum glucose averaged from 8 patients each from Arm 1 and Arm 2 in the clinical trial over a 6-hour sampling period. Patients who consumed the RTDS showed a marked decrease in peak postprandial serum glucose and remained below the standard nutritional supplement cohort. These results indicate that an EMO-based nutritional supplement with a high amount of 1-monoacylglycerol such as 1-oleoyl monoglycerol was able to have a beneficial effect on glucose homeostasis compared to a standard nutritional supplement by PERT that is expected to produce only a small amount of 2-monoacylglycerol such as 2-oleoyl monoglycerol. Based on the amount of glucose administered, a higher serum glucose level was expected for the RTDS cohort, and the effect shown was unexpected.

[0182] Figure 10 shows the levels of serum triglycerides averaged from 8 patients each from Arm 1 and Arm 2 in the clinical trial over a 6-hour sampling period. Both the test group and the control group showed similar triglyceride levels, indicating that the patients absorbed the same amount of lipids from either the standard nutritional supplement by PERT or the RTDS without PERT.

[0183] Example 8: High-Calorie, PERT-Free Ready-to-Drink Shake The high-calorie RTDS can be prepared as follows: Add DI water (about 60% of the final volume) to the main mixing container and heat to about 60°C. Mix the hydrolyzed protein and then add the agave syrup. Combine using a hand mixer. In a separate container, combine the warm (60°C) EMO and lecithin. Once the lecithin has dissolved, add the EMO / lecithin to the aqueous phase and mix. Add additional water to make the final weight (volume). Emulsify using a shear blender. To prepare a very high-calorie RTDS, add higher levels of the ingredients.

[0184] Following the production of the beverage base, various flavors, maskers, and blockers can be added to produce unique products such as chocolate, vanilla, and strawberry.

[0185] Also, this method can be used to produce high-calorie products in semi-solid forms such as puddings, mousses, "pops," and ice cream-like products by adding viscosity modifiers such as xanthan gum and acacia gum using the beverage base recipe.

[0186] Table 6 shows the main components and nutritional values of high-calorie (1.5 kcal / mL) RTDS.

Table 6

[0187] Table 7 shows the main components and nutritional values of very high-calorie (2.5 kcal / mL) RDTS.

Table 7

[0188] Example 9: High-Calorie, PERT-Free Bar The high-calorie bar can be prepared as follows. Add DI water (about 60% of the final volume) to the main mixing container and heat to about 60°C. Mix the hydrolyzed protein and then add the agave syrup. In a separate container, combine warm (60°C) EMO and lecithin using a hand mixer. Once the lecithin has dissolved, add the EMO / lecithin to the aqueous phase and mix. Add additional water to bring to the final weight (volume).

[0189] Table 8 shows the main components and nutritional values of the high-calorie, PERT-free bar.

Table 8

[0190] After the base is manufactured and before baking, various flavors, maskers, and blockers can be added to produce unique products such as chocolate and vanilla.

[0191] Example 10: Production of Ready-to-Drink Shakes Add DI water to the main mixing container and heat to approximately 60 °C + / - 2 °C. Once the water reaches 60 °C, add sugar syrup (such as agave syrup or date syrup) while stirring slowly. Mix to form a solution. Weigh the dry weights of the individual substances (vitamin / mineral mixture and hydrolyzed protein) and combine them in a separate container. Thoroughly mix the dry ingredients. Slowly and directly add the mixed dry ingredients to the main mixing container while sweep-stirring with gentle agitation. Weigh the EMO in a separate container. Heat the EMO to 60 °C + / - 2 °C. Slowly add the sunflower lecithin to the EMO and mix (if necessary) with moderate agitation until the sunflower lecithin is completely mixed into the solution. Slowly add the EMO / sunflower lecithin mixture to the main mixing container. Add distilled water to increase the volume to 95% of the total fluid mass and return the temperature to 70 °C + / - 2 °C. Slowly add flavor and coloring agents to the main mixing container. Slowly add a stabilizer (such as acacia gum) to the main mixing container. Mix the solution for 20 minutes (to increase the viscosity). Maintain the temperature of the solution at 70 °C + / - 2 °C. Add an appropriate amount of distilled water to bring the solution to its final volume. Pass the material through a pressure drop homogenizer(s) to produce a stable emulsion. Pasteurize or sterilize the material. Cool the material to room temperature. Fill the product into packages.

[0192] Example 11: Removal of MCPD from Almond Oil The enzyme-modified almond oil was prepared as described in Example 6.

[0193] Samples of enzymatically modified almond oil were sent to a third-party laboratory (Eurofins Eurofins Scientific Inc. Nutrition Analysis Center 2200 Rittenhouse Street, Suite 150 Des Moines, IA 50321) for analysis using the standard methods described below.

[0194] AOCS Official Method Cd 29b-13 (Revised 2017) - Determination of 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. Also refer to AOCS Official Methods Cd 29a-13 or Cd 29c-13. Bound glycidol is the sum of all glycidyl derivatives 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 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 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 concurrent determination of glycidol along with 2-MCPD and 3-MCPD, present in either bound or free form in oils and fats. This method is based on alkaline-catalyzed ester cleavage, conversion of the liberated glycidol to monobromopropanediol (MBPD), and derivatization of the free diols (MCPD and MBPD) with phenylboronic acid (PBA). Free MCPD and glycidol are present in oils and fats only in small to negligible amounts, but significant contents will increase in proportion to the determined amounts of the bound analytes. This method is applicable to solid and liquid fats and oils.

[0195] Results. The total 2-MCPD (free and bound) and total 3-MCPD (free and bound) in the starting oil were 0.65 mg / kg and 1.17 mg / kg, respectively. The enzyme-modified almond oil (Example 6) had total 2-MCPD (free and bound) and total 3-MCPD (free and bound) of less than 0.10 mg / kg each, below the lower limit of quantification (0.10 mg / kg) of the assay for measuring MCPD. Thus, the total MCPD detected in the starting almond oil and the enzyme-modified oil were 1.82 mg / kg and less than 0.10 mg / kg, respectively.

[0196] Accordingly, the present invention is well adapted to attain the ends and advantages mentioned as well as those inherent therein. Many changes may be made by those skilled in the art, and such changes are encompassed within the spirit of the invention as partially shown by the appended claims.

[0197] Example 12: Fatty acid profiles of starting oil and MAG oil MCT, canola and almond oils were processed according to the production method of the present disclosure. As shown in Table 9 below, the fatty acid profile of each was measured in both the starting oil and the MAG oil.

[0198] The fatty acids were analyzed as fatty acid methyl esters after derivatization and compared to standards. For derivatization, the sample (500 μl) was added to a 5 ml reaction tube containing 2 ml of boron trifluoride solution (12% in methanol), 20 μl of dimethoxypropane, and 100 μl of tridecane acid internal standard solution (10 mg / ml). The reaction tube was vortexed and incubated in a heat block at 60 °C for 30 minutes. The reaction tube was removed from the heat block and cooled 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 separated for 3 minutes. The upper (hydrophobic) phase was transferred to a 1.5 ml tube containing approximately 50 mg of sodium sulfate (anhydrous). After vortexing for 60 seconds, the 1.5 ml tube was centrifuged and approximately 500 μl of the clarified dry hydrophobic phase was transferred to a gas chromatography sample vial. The sample was analyzed using an Agilent 7890A gas chromatograph with a flame ionization detector and Agilent Openlab CDS Chemstation software. GC column: Omegawax 100 (15 m × 0.1 mm × 0.1 μm) column. The results were converted to weight % by internal standard reference.

Table 9

[0199] As shown, both the starting oil and the MAG oil contained substantially the same fatty acid profile.

[0200] Another experiment was conducted using almond oil and canola oil, and the data in Table 10 were obtained, showing the same results for oleic acid, linoleic acid, and linolenic acid.

Table 10

[0201] These results demonstrate that the fatty acid profile of the starting oil in MAG oil can be preserved by the manufacturing process of the present disclosure. These results differ from conventional "distilled" oils in that their fatty acid profiles are significantly different from the starting oil based on the functional use of the distilled oil.

[0202] These results also demonstrate that the processing oil of the present disclosure can provide "complete nutrition" by providing linoleic acid and linolenic acid. Similar results are expected for high EPA and high DHA oils such as fish oil and algal oil to provide complete nutrition formulations.

[0203] Example 13: The EMO process preserves the essential fatty acids contained in the original oil Canola EMO was manufactured as described in Example 1. Fatty acids were measured as described in Example 2. Figure 11 shows the results of the fatty acid analysis. Canola oil and EMO produced from canola oil maintain the integrity of the fatty acid profile and contain the essential fatty acids linoleic acid and linolenic acid. Similar results were obtained for EMO from olive oil, sunflower oil, and almond oil. Commercially available "monostearin" (Profood Products, Naperville, IL) contains little or no unsaturated fatty acids, and "Capmul GMO50" (Abitec Corporation, Janesville, WI) is mainly the monounsaturated fatty acid, oleic acid, contains little linoleic acid, and substantially no fatty acids of linolenic acid or gondoic acid (C20:1).

[0204] Example 14: Beneficial compounds are preserved Vegetable oils contain trace amounts of many lipids, steroids, esters, and phenolic compounds, which contribute to the taste and health benefits of the oil. Many of these compounds are preserved or concentrated in the EMO process. This is shown 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. Briefly, 150 μL of standard (0.1 - 100 μg / mL) and 20 μL of internal standard mixture were mixed and dried under nitrogen. To the dried residue, 200 μL of oxalyl chloride (2M in dichloromethane) was added, and the mixture was incubated on a heat block at 65 °C for 5 minutes and then dried under nitrogen. To the residue, 150 μL of 3-picolylamine (1% in acetonitrile, v / v) was added to form 3-picolylamide (FA-PA). The mixture was incubated at room temperature for 5 minutes and then dried under nitrogen to obtain derivatized FA. The dried FA derivative was dissolved in 1000 μL of ethanol and further diluted 10-fold with ethanol before LC-MS analysis. LC-MS analysis was performed in ionization modes: positive ionization (total fatty acids and lipid mix) and negative ionization (lipid mix). Software used for analysis: Thermo Scientific Freestyle&LipidSearch. Orbitrap fusion method: data-dependent acquisition MS 2 (Total fatty acids)&MS.

[0205] Compounds that are preserved or enhanced include: glycosphingolipids (e.g., ceramide phosphate), glyceroglycolipids (e.g., monogalactosyldiacylglycerol), phosphatidylmethanol, steroids (e.g., sitosteryl ester), neutral lipids (e.g., campesteryl ester), sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin. Coenzymes were also found to be enhanced.

[0206] These compounds are not retained in commercial (distillate) monoglyceride products.

[0207] In the first embodiment, the food contains oil, has a total calorie content of about 25 kcal to about 1,000 kcal, and about 5% to about 75% of the total calorie content is derived from the oil. The oil contains less than 10% by weight of triacylglycerol (TAG) based on the total weight of the oil, and the oil is substantially free of 3-monochloropropane-1,2-diol (MCPD).

[0208] In one aspect of the first embodiment, the oil contains more than 50% by weight of monoacylglycerol (MAG) based on the total weight of the oil.

[0209] In another aspect of the first embodiment, the oil contains more than 60% by weight of MAG based on the total weight of the oil.

[0210] In another aspect of the first embodiment, the oil contains more than 70% by weight of MAG based on the total weight of the oil.

[0211] In another aspect of the first embodiment, the oil contains more than 80% by weight of MAG based on the total weight of the oil.

[0212] In another aspect of the first embodiment, the oil contains more than 90% by weight of MAG based on the total weight of the oil.

[0213] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, about 10% to about 60% of the total calorie content is derived from the oil.

[0214] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, about 20% to about 50% of the total calorie content is derived from the oil.

[0215] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, about 25% to about 45% of the total calorie content is derived from the oil.

[0216] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, about 30% to about 40% of the total calorie content is derived from the oil.

[0217] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further comprises a carbohydrate source.

[0218] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further comprises a carbohydrate source, and the carbohydrate source comprises fruit or agave syrup.

[0219] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further comprises a carbohydrate source, and the carbohydrate source comprises monosaccharides.

[0220] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further comprises a carbohydrate source, and about 20% to about 50% of the calories are derived from the carbohydrate source.

[0221] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food comprises a carbohydrate source and further comprises a protein source.

[0222] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food comprises a carbohydrate source and further comprises a protein source, and about 10% to about 50% of the calories are derived from the protein source.

[0223] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food comprises a carbohydrate source and further comprises a protein source, and the protein source comprises hydrolyzed or partially hydrolyzed protein.

[0224] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food includes a carbohydrate source and further includes a protein source, the protein source includes hydrolyzed or partially hydrolyzed protein, and the hydrolyzed protein is selected from hydrolyzed legume protein and whey-based hydrolysis products.

[0225] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further includes a protein source.

[0226] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further includes a protein source, and about 10% to about 50% of the calories are derived from the protein source.

[0227] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further includes a protein source, the protein source includes hydrolyzed or partially hydrolyzed protein.

[0228] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the food further includes a protein source, the protein source includes hydrolyzed or partially hydrolyzed protein, and the hydrolyzed protein is selected from hydrolyzed legume protein and whey-based hydrolysis products.

[0229] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the oil is a processed oil derived from an oil source.

[0230] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, and thus, no non-oil components are added to the processed oil.

[0231] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof.

[0232] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is tocopherol.

[0233] In another aspect of the first embodiment, or in any of the foregoing aspects of the first embodiment, the oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, the antioxidant is tocopherol, and the tocopherol is selected from α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, and γ-tocotrienol.

[0234] In the second embodiment, the food contains a processed oil, a carbohydrate source, and a protein source, has a calorie density of about 1 kcal to about 5 kcal per gram, and has a total weight of about 25 grams to about 500 grams, the processed oil contains about 10% to about 50% of the total calorie content, the processed oil has an MAG content of 40% by weight or more based on the total weight of the processed oil and a TAG content of 10% by weight or less based on the total weight of the processed oil, and the processed oil has an MCPD of less than 0.10 mg / kg.

[0235] In the third embodiment, the product contains a processed oil derived from an oil source, the processed oil contains a MAG content of 40% by weight or more of the total weight of the processed oil, the processed oil contains no TAG or contains a TAG content of 10% by weight or less of the total weight of the processed oil, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, the oil source contains from about 1.00 mg / kg to about 12.00 mg / kg of MCPD, and the processed oil contains less than 0.100 mg / kg of MCPD.

[0236] In one aspect of the third embodiment, the oil source is derived from a source selected from plants, animals, algae, or fish.

[0237] In another aspect of the third embodiment, the oil source is of plant origin.

[0238] In another aspect of the third embodiment, the oil source is selected from the group consisting of olive oil, sunflower oil, corn oil, almond oil, rapeseed oil, palm oil, soybean oil, linseed oil, and mixtures thereof.

[0239] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the non-oily component is selected from the group consisting of antioxidants, vitamins, and mixtures thereof.

[0240] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the non-oil component is selected from the group consisting of antioxidants, vitamins, and mixtures thereof, and the antioxidant is tocopherol.

[0241] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the non-oil component is 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 α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, and γ-tocotrienol.

[0242] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the processing oil contains a MAG content of about 50 wt% to about 95 wt% based on the total weight of the processing oil.

[0243] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the processing oil contains a MAG content of about 50 wt% to about 95 wt% based on the total weight of the processing oil, and the processing oil contains a TAG content of about 5 wt% to about 0.5 wt% based on the total weight of the processing oil.

[0244] In another aspect of the third embodiment, or in any of the foregoing aspects of the third embodiment, the processing oil contains a TAG content of about 5 wt% to about 0.5 wt% based on the total weight of the processing oil.

[0245] In a fourth embodiment, a method for producing oil enriched in monoacylglycerol comprises: starting oil containing triacylglycerol (TAG) and about 1.00 mg / kg to about 12.00 mg / kg of MCPD (TAG is in an amount greater than 50% by weight based on the total weight of the starting oil), mixing with a buffer and a first enzyme capable of hydrolyzing the TAG into free fatty acids (FFA) to produce a first reaction mixture; reacting the first reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG for a first period to produce a first lipid reaction product containing an aqueous phase and FFA; inactivating the first enzyme in the first lipid reaction product; recovering the first lipid reaction product by removing it from the aqueous phase; mixing the first lipid reaction product with a second enzyme capable of esterifying food-grade glycerol and FFA to form a second reaction mixture; reacting the second reaction mixture for a second period to produce a second lipid reaction product containing a lipid oil phase and a glycerol phase; inactivating the second enzyme in the second lipid reaction product; adding salt to the reaction product and separating the lipid oil phase from the glycerol phase; and recovering the lipid oil phase, wherein the lipid oil phase is substantially free of MCPD.

[0246] In one aspect of the fourth embodiment, the starting oil is an oil derived from a plant, animal, or fish origin.

[0247] In another aspect of the fourth embodiment, the starting oil is a vegetable oil or a mixture of vegetable oils.

[0248] In another aspect of the fourth embodiment, the starting oil is a vegetable oil selected from the group consisting of olive oil, sunflower oil, corn oil, almond oil, rapeseed oil, palm oil, soybean oil, linseed oil, and mixtures thereof.

[0249] In another aspect of the fourth embodiment, the first enzyme is lipase.

[0250] In another aspect of the fourth embodiment, the first enzyme is lipase AY.

[0251] In another aspect of the fourth embodiment, the buffer solution is a sodium citrate solution.

[0252] In another aspect of the fourth embodiment, the first period is a period sufficient to hydrolyze at least 94% of the TAG in the starting oil.

[0253] In another aspect of the fourth embodiment, the first period is from about 14 to about 24 hours.

[0254] In another aspect of the fourth embodiment, the step of reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG is carried out at a temperature of about 30°C to about 35°C.

[0255] In another aspect of the fourth embodiment, a starting oil containing triacylglycerol (TAG), a buffer solution, and a first enzyme capable of hydrolyzing the TAG into free fatty acids (FFA) are mixed, and the step of reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG into FFA is carried out under a nitrogen atmosphere.

[0256] In another aspect of the fourth embodiment, the second enzyme is lipase.

[0257] In another aspect of the fourth embodiment, the second enzyme is lipase G.

[0258] In another aspect of the fourth embodiment, the second period is a period sufficient to result in the enrichment of MAG in the lipid oil phase of about 60% to 95%.

[0259] In another aspect of the fourth embodiment, the second period is from about 24 hours to about 72 hours.

[0260] In another aspect of the fourth embodiment, the step of reacting the second reaction mixture for a second period to produce a lipid oil phase and a glycerol phase is carried out at a temperature of about 17°C to 23°C.

[0261] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the method further comprises drying the second lipid reaction product by applying a third period of vacuum sufficient to remove at least a portion of the water from the second lipid reaction product.

[0262] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the method further comprises drying the second lipid reaction product by applying a third period of vacuum sufficient to remove at least a portion of the water from the second lipid reaction product, and the step of drying the second lipid reaction product is carried out at a temperature of 20°C to 30°C.

[0263] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the method further comprises drying the second lipid reaction product by applying a third period of vacuum sufficient to remove at least a portion of the water from the second lipid reaction product, and the drying step is applied throughout the second period.

[0264] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the step of inactivating the second enzyme is carried out by heating the second lipid reaction product.

[0265] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the step of inactivating the second enzyme is carried out by heating the second lipid reaction product, and the heating is carried out at a temperature of at least 70°C for at least 1 hour.

[0266] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the step of separating the lipid oil phase from the glycerol phase includes adding sodium chloride to the second lipid reaction product.

[0267] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the step of separating the lipid oil phase from the glycerol phase includes adding sodium chloride to the second lipid reaction product, and the final concentration of sodium chloride includes up to 0.3% by weight of sodium chloride.

[0268] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the method further includes reconstructing a nitrogen atmosphere over the first lipid reaction product before mixing the first lipid reaction product with food-grade glycerol and a second enzyme capable of esterifying FFA and glycerol.

[0269] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the method further includes adding tocopherol to the lipid oil phase after recovering the lipid oil phase.

[0270] In another aspect of the fourth embodiment, or in any of the foregoing aspects of the fourth embodiment, the lipid oil phase contains MAG in an amount of about 40% to about 99% by weight based on the total weight of the lipid oil phase, and the lipid oil phase either does not contain TAG or contains TAG in an amount of about 0.1% to about 10% by weight based on the total weight of the lipid oil phase.

[0271] In the fifth embodiment, the processed oil contains monoglyceryl oleate (MOG) and has a total fatty acid content, and the MOG constitutes about 5% to about 75% of the total fatty acid content of the processed oil.

[0272] In one aspect of the fifth embodiment, the processed oil contains less than 10% by weight of triacylglycerol (TAG) based on the total weight of the processed oil.

[0273] In another aspect of the fifth embodiment, the processing oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processing oil.

[0274] In another aspect of the fifth embodiment, the processing oil contains more than 60% by weight of monoacylglyceride (MAG) based on the total weight of the processing oil.

[0275] In another aspect of the fifth embodiment, the processing oil contains more than 70% by weight of monoacylglyceride (MAG) based on the total weight of the processing oil.

[0276] In another aspect of the fifth embodiment, the processing oil contains more than 80% by weight of monoacylglyceride (MAG) based on the total weight of the processing oil.

[0277] In another aspect of the fifth embodiment, the processing oil contains more than 90% by weight of monoacylglyceride (MAG) based on the total weight of the processing oil.

[0278] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil is a processing oil derived from an oil source.

[0279] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil is a processing oil derived from an oil source, the processing oil is derived from the oil source and contains non-oil components naturally present in the oil source, and thus no non-oil components are added to the processing oil.

[0280] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil is a processing oil derived from an oil source, the processing oil is derived from the oil source and contains non-oil components naturally present in the oil source, and thus no non-oil components are added to the processing oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof.

[0281] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is tocopherol.

[0282] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil is a processed oil derived from an oil source, the processed oil is derived from the oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil, the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, the antioxidant is tocopherol, and the tocopherol is selected from α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, and γ-tocotrienol.

[0283] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil is substantially free of 3-monochloropropane-1,2-diol (MCPD).

[0284] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil has less than 0.10 mg / kg of 3-monochloropropane-1,2-diol (MCPD).

[0285] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the oil source is derived from a source selected from plants, animals, algae, or fish.

[0286] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the oil source is plant-derived.

[0287] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the oil source is selected from the group consisting of safflower oil, grape oil, maria thistle 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.

[0288] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil contains a MAG content of about 50 wt% to about 95 wt% based on the total weight of the processed oil.

[0289] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil contains a TAG content of about 5 wt% to about 0.5 wt% based on the total weight of the processed oil.

[0290] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the MOG in the processed oil contains at least 50 wt% of 1-oleoyl monoglyceride of the total amount of MOG.

[0291] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the MOG in the processed oil contains at least 60 wt% of 1-oleoyl monoglyceride of the total amount of MOG.

[0292] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the MOG in the processed oil contains at least 70 wt% of 1-oleoyl monoglyceride of the total amount of MOG.

[0293] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the MOG in the processed oil contains at least 80 wt% of 1-oleoyl monoglyceride of the total amount of MOG.

[0294] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil further contains linoleic acid, and the linoleic acid is present in the processing oil in an amount of about 1.5 wt% to about 90 wt% of the total fatty acid content of the processing oil.

[0295] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil further contains linoleic acid, and the linoleic acid is present in the processing oil in an amount of about 10 wt% to about 90 wt% of the total fatty acid content of the processing oil.

[0296] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil further contains linoleic acid, and the linoleic acid is present in the processing oil in an amount of about 20 wt% to about 90 wt% of the total fatty acid content of the processing oil.

[0297] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil further contains linoleic acid, and the linoleic acid is present in the processing oil in an amount of about 10 wt% to about 25 wt% of the total fatty acid content of the processing oil.

[0298] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processing oil further contains linolenic acid, and the linolenic acid is present in the processing oil in an amount of about 0.01 wt% to about 2 wt% of the total fatty acid content of the processing oil.

[0299] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linoleic acid in the processing oil is about 0.01 to about 5.

[0300] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linoleic acid in the processing oil is about 1 to about 4.

[0301] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linoleic acid in the processed oil is from about 3 to about 4.

[0302] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linolenic acid in the processed oil is from about 1 to about 100.

[0303] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linolenic acid in the processed oil is from about 10 to 100.

[0304] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the ratio of the amount of oleic acid to linolenic acid in the processed oil is from about 10 to 30.

[0305] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, 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 is produced.

[0306] In one aspect of the foregoing aspects, the fatty acid profile includes oleic acid, linoleic acid, and linolenic acid.

[0307] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 10% of the amounts of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil is produced.

[0308] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 1% of the amounts of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil is produced.

[0309] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil contains three times the amount of MAG compared to the amount of TAG in the pre-processed oil from which the processed oil is produced.

[0310] In another aspect of the fifth embodiment, or in any of the foregoing aspects of the fifth embodiment, the processed oil contains oleic acid in the form of monoglyceryl oleate in an amount approximately the same as the amount of oleic acid in the pre-processed oil from which the processed oil is produced.

[0311] In the sixth embodiment, the processed oil has a fatty acid profile including oleic acid, linoleic acid, and linolenic acid, and the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 10% of the amounts of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil is produced, and the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0312] In the seventh embodiment, the processed oil has a fatty acid profile including oleic acid, linoleic acid, and linolenic acid, and the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 1% of the amounts of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil is produced, and the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0313] In the eighth embodiment, the processed oil contains oleic acid and linoleic acid, and the ratio of oleic acid to linoleic acid in the processed oil is from about 0.01 to about 5, and the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0314] In one aspect of the eighth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is from about 1 to about 4.

[0315] In another aspect of the eighth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is from about 3 to about 4.

[0316] In another aspect of the eighth embodiment, or in any of the foregoing aspects of the eighth embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linolenic acid in the processing oil is from about 1 to about 100.

[0317] In another aspect of the eighth embodiment, or in any of the foregoing aspects of the eighth embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 100.

[0318] In another aspect of the eighth embodiment, or in any of the foregoing aspects of the eighth embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 30.

[0319] In the ninth embodiment, the processing oil contains oleic acid and linolenic acid, the ratio of oleic acid to linolenic acid in the processing oil is from about 1 to about 100, and the processing oil contains more than 50% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil.

[0320] In the tenth embodiment, the processing oil contains oleic acid and linolenic acid, the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 100, and the processing oil contains more than 50% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil.

[0321] In the eleventh embodiment, the processing oil contains oleic acid and linolenic acid, the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 30, and the processing oil contains more than 50% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil.

[0322] In one aspect of the ninth, tenth, or eleventh embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linoleic acid in the processing oil is from about 0.01 to about 5.

[0323] In one aspect of the ninth, tenth, or eleventh embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linoleic acid in the processing oil is from about 1 to about 4.

[0324] In one aspect of the ninth, tenth, or eleventh embodiment, the processing oil further contains linoleic acid, and the ratio of oleic acid to linoleic acid in the processing oil is from about 3 to about 4.

[0325] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the aforementioned aspects of the eighth, ninth, tenth, or eleventh embodiment, at least a portion of the oleic acid is present in the form of oleic acid monoglyceride (MOG).

[0326] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the aforementioned aspects of the eighth, ninth, tenth, or eleventh embodiment, at least a portion of the oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 50% by weight of the total amount of MOG is 1-oleyl monoglyceride.

[0327] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the aforementioned aspects of the eighth, ninth, tenth, or eleventh embodiment, at least a portion of the oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 60% by weight of the total amount of MOG is 1-oleyl monoglyceride.

[0328] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the aforementioned aspects of the eighth, ninth, tenth, or eleventh embodiment, at least a portion of the oleic acid is present in the form of oleic acid monoglyceride (MOG), and at least 70% by weight of the total amount of MOG is 1-oleyl monoglyceride.

[0329] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, at least a part of the oleic acid is present in the form of monoglyceryl oleate (MOG), and at least 80% by weight of the total amount of MOG is 1-oleoyl monoglyceride.

[0330] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains less than 10% by weight of triacylglyceride (TAG) based on the total weight of the processed oil.

[0331] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0332] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains more than 60% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0333] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains more than 70% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0334] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains more than 80% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0335] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil contains more than 90% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0336] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil is derived from an oil source.

[0337] In one aspect of the foregoing aspects, the processed oil is derived from an oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processed oil.

[0338] In one aspect of the foregoing aspects, the non-oily components are selected from antioxidants, vitamins, and mixtures thereof.

[0339] In one aspect of the foregoing aspects, the antioxidant is tocopherol.

[0340] In one aspect of the foregoing aspects, the tocopherol is selected from α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, and γ-tocotrienol.

[0341] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil substantially does not contain 3-monochloropropane-1,2-diol (MCPD).

[0342] In the aspects of the eighth, ninth, tenth, or eleventh embodiment, and in any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil has less than 0.10 mg / kg of 3-monochloropropane-1,2-diol (MCPD).

[0343] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the foregoing aspects of the 8th, 9th, 10th, or 11th embodiment, the oil source is derived from a source selected from plants, animals, algae, or fish.

[0344] In one aspect of the foregoing aspects, the oil source is of plant origin.

[0345] In one aspect of the foregoing aspects, the oil source is selected from the group consisting of safflower oil, grape oil, marigold 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.

[0346] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the foregoing aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains an MAG content of about 50 wt% to about 95 wt% based on the total weight of the processed oil.

[0347] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the foregoing aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains a TAG content of about 5 wt% to about 0.5 wt% based on the total weight of the processed oil.

[0348] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the foregoing aspects of the 8th, 9th, 10th, or 11th embodiment, 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 is produced.

[0349] In one aspect of the foregoing aspects, the fatty acid profile includes oleic acid, linoleic acid, and linolenic acid.

[0350] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 10% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0351] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 1% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0352] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains three times the amount of MAG compared to the amount of TAG in the pre-processed oil from which the processed oil is produced.

[0353] In the aspects of the 8th, 9th, 10th, or 11th embodiment, and in any of the aforementioned aspects of the 8th, 9th, 10th, or 11th embodiment, the processed oil contains oleic acid in the form of oleic acid monoglyceride in an amount substantially the same as the amount of oleic acid in the pre-processed oil from which the processed oil is produced.

[0354] In the 12th embodiment, the processed oil contains oleic acid and linoleic acid and has a total fatty acid content, and the linoleic acid is present in an amount of about 10 wt% to about 90 wt% of the total fatty acid content of the processed oil, and the processed oil contains more than 50 wt% of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0355] In one aspect of the 12th embodiment, the linoleic acid is present in an amount of about 20 wt% to about 90 wt% of the total fatty acid content of the processed oil.

[0356] In another aspect of the 12th embodiment, the linoleic acid is present in an amount of about 10 wt% to about 25 wt% of the total fatty acid content of the processed oil.

[0357] In any of the aspects of the twelfth embodiment or the aforementioned aspects of the twelfth embodiment, the processing oil further contains linolenic acid, and the linolenic acid is present in an amount of about 0.01% by weight to about 2% by weight of the total fatty acid content of the processing oil.

[0358] In any of the aspects of the twelfth embodiment or the aforementioned aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processing oil is from about 0.01 to about 5.

[0359]

[0360] In any of the aspects of the twelfth embodiment or the aforementioned aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processing oil is from about 1 to about 4.

[0361] In any aspect of the twelfth embodiment or any of the aforementioned aspects of the twelfth embodiment, the ratio of oleic acid to linolenic acid in the processing oil is from about 1 to about 100.

[0362] In any aspect of the twelfth embodiment or any of the aforementioned aspects of the twelfth embodiment, the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 100.

[0363] In any aspect of the twelfth embodiment or any of the aforementioned aspects of the twelfth embodiment, the ratio of oleic acid to linolenic acid in the processing oil is from about 10 to about 30.

[0364] In any of the aspects of the twelfth embodiment or the aforementioned aspects of the twelfth embodiment, at least a part of the oleic acid is present in the form of oleic acid monoglyceride (MOG).

[0365] ​In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, MOG in the processed oil contains at least 50% by weight of 1-oleoyl monoglyceride out of the total amount of MOG.

[0366] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, MOG in the processed oil contains at least 60% by weight of 1-oleoyl monoglyceride out of the total amount of MOG.

[0367] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, MOG in the processed oil contains at least 70% by weight of 1-oleoyl monoglyceride out of the total amount of MOG.

[0368] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, MOG in the processed oil contains at least 80% by weight of 1-oleoyl monoglyceride out of the total amount of MOG.

[0369] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, the processed oil contains less than 10% by weight of triacylglyceride (TAG) based on the total weight of the processed oil.

[0370] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0371] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, the processed oil contains more than 60% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0372] In either the aspect of the 12th embodiment or any of the aforementioned aspects of the 12th embodiment, the processed oil contains more than 70% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0373] In either the aspect of the twelfth embodiment or any of the foregoing aspects of the twelfth embodiment, the processing oil contains more than 80% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil.

[0374] In either the aspect of the twelfth embodiment or any of the foregoing aspects of the twelfth embodiment, the processing oil contains more than 90% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil.

[0375] In either the aspect of the twelfth embodiment or any of the foregoing aspects of the twelfth embodiment, the processing oil is a processing oil derived from an oil source.

[0376] In one aspect of the foregoing aspects, the processing oil is derived from an oil source and contains non-oil components naturally present in the oil source, so that no non-oil components are added to the processing oil.

[0377] In one aspect of the foregoing aspects, the non-oily components are selected from antioxidants, vitamins, and mixtures thereof.

[0378] In one aspect of the foregoing aspects, the antioxidant is tocopherol.

[0379] In one aspect of the foregoing aspects, the tocopherol is selected from α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, α-tocotrienol, β-tocotrienol, δ-tocotrienol, and γ-tocotrienol.

[0380] In either the aspect of the twelfth embodiment or any of the foregoing aspects of the twelfth embodiment, the processing oil substantially does not contain 3-monochloropropane-1,2-diol (MCPD).

[0381] In one aspect of the twelfth embodiment or any of the foregoing aspects of the twelfth embodiment, the processing oil has less than 0.10 mg / kg of 3-monochloropropane-1,2-diol (MCPD).

[0382] In either the aspect of the twelfth embodiment or the above-described aspect of the twelfth embodiment, the oil source is derived from a source selected from plants, animals, algae, or fish.

[0383] In one aspect of the above-described aspect, the oil source is plant-derived.

[0384] In one aspect of the above-described aspect, the oil source is selected from the group consisting of safflower oil, grape oil, maria thistle 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.

[0385] In either the aspect of the twelfth embodiment or the above-described aspect of the twelfth embodiment, the processed oil contains an MAG content of about 50 wt% to about 95 wt% based on the total weight of the processed oil.

[0386] In either the aspect of the twelfth embodiment or the above-described aspect of the twelfth embodiment, the processed oil contains a TAG content of about 5 wt% to about 0.5 wt% based on the total weight of the processed oil.

[0387] In either the aspect of the twelfth embodiment or the above-described aspect of the twelfth embodiment, 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 is produced.

[0388] In one aspect of the above-described aspect, the fatty acid profile includes oleic acid, linoleic acid, and linolenic acid.

[0389] In either one aspect of the twelfth embodiment or the above-described aspect of the twelfth embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 10% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0390] In one aspect of the twelfth embodiment, or in any of the foregoing aspects of the twelfth embodiment, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 1% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced.

[0391] In an aspect of the twelfth embodiment, or in any of the foregoing aspects of the twelfth embodiment, the processed oil contains substantially the same amount of MAG as the amount of TAG in the pre-processed oil from which the processed oil is produced.

[0392] In one aspect of the twelfth embodiment, or in any of the foregoing aspects of the twelfth embodiment, the processed oil contains oleic acid in the form of oleic acid monoglyceride in an amount substantially the same as the amount of oleic acid in the pre-processed oil from which the processed oil is produced.

[0393] In the thirteenth embodiment, the processed oil has a fatty acid profile that includes oleic acid, linoleic acid, and linolenic acid, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 10% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced, and the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0394] In the fourteenth embodiment, the processed oil has a fatty acid profile that includes oleic acid, linoleic acid, and linolenic acid, the amounts of oleic acid, linoleic acid, and linolenic acid in the processed oil are each within about 1% of the amounts of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is produced, and the processed oil contains more than 50% by weight of monoacylglyceride (MAG) based on the total weight of the processed oil.

[0395] In the fifteenth embodiment, a method of promoting glucose homeostasis in a subject in need thereof includes administering to the subject a composition comprising the processed oil.

[0396] In the 16th embodiment, a method for treating a subject in need of treatment for type II diabetes comprises administering to the subject a composition comprising a processed oil.

[0397] In the 17th embodiment, a method for promoting glucose homeostasis in a subject in need thereof comprises administering to the subject a composition comprising a processed oil containing monoglyceryl oleate (MOG), wherein at least 50% by weight of the MOG is 1-oleoyl monoglyceride.

[0398] In the 18th embodiment, a method for treating a subject in need of treatment for diabetes comprises administering to the subject a composition comprising a processed oil containing monoglyceryl oleate (MOG), wherein at least 50% by weight of the MOG is 1-oleoyl monoglyceride.

[0399] In one aspect of the 17th or 18th embodiment, at least 60% by weight of the MOG is 1-oleoyl monoglyceride.

[0400] In another aspect of the 17th or 18th embodiment, at least 70% by weight of the MOG is 1-oleoyl monoglyceride.

[0401] In another aspect of the 17th or 18th embodiment, at least 80% by weight of the MOG is 1-oleoyl monoglyceride.

[0402] In an aspect of the 15th, 16th, 17th, or 18th embodiment, or any of the foregoing aspects of the 17th or 18th embodiment, the processed oil is a processed oil according to any one of the 5th to 14th embodiments and any of the foregoing aspects thereof.

[0403] In any aspect of the 15th, 16th, 17th, or 18th embodiment, or any aspect of any of the foregoing aspects of the 15th, 16th, 17th, or 18th embodiment, the composition is a food comprising a processed oil of any of the 1st, 2nd, or 3rd embodiments and any of the foregoing aspects thereof.

[0404] In one aspect of the 15th or 17th embodiment, or in any of the foregoing aspects of the 15th or 17th embodiment, the subject is suffering from a condition that affects glucose homeostasis.

[0405] In one aspect of the foregoing aspect, the condition is insulin resistance or type II diabetes.

[0406] In an aspect of the 5th, 6th, or 7th embodiment, or in any of the foregoing aspects of the 5th, 6th, or 7th embodiment, the MOG contributes from about 10% to about 75% by weight of the total fatty acid content of the processed oil.

[0407] In an aspect of the 5th, 6th, or 7th embodiment, or in any of the foregoing aspects of the 5th, 6th, or 7th embodiment, the MOG contributes from about 20% to about 75% by weight of the total fatty acid content of the processed oil.

[0408] In an aspect of the 5th, 6th, or 7th embodiment, or in any of the foregoing aspects of the 5th, 6th, or 7th embodiment, the MOG contributes from about 30% to about 75% by weight of the total fatty acid content of the processed oil.

[0409] In an aspect of the 5th, 6th, or 7th embodiment, or in any of the foregoing aspects of the 5th, 6th, or 7th embodiment, the MOG contributes from about 40% to about 75% by weight of the total fatty acid content of the processed oil.

[0410] In an aspect of the 5th, 6th, or 7th embodiment, or in any of the foregoing aspects of the 5th, 6th, or 7th embodiment, the MOG contributes from about 50% to about 75% by weight of the total fatty acid content of the processed oil.

[0411] In the aspect of the fifth, sixth, or seventh embodiment, or in any of the foregoing aspects of the fifth, sixth, or seventh embodiment, the MOG contributes to about 60 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0412] In the aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or in any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount that contributes to 5 wt% to about 75 wt% of the fatty acid content of the processed oil.

[0413] In the aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or in any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount that contributes to about 10 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0414] In the aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or in any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount that contributes to about 20 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0415] In the aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or in any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount that contributes to about 30 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0416] In the aspect of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, or in any of the foregoing aspects of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount contributing to about 40 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0417] In the aspect of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, or in any of the foregoing aspects of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount contributing to about 50 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0418] In the aspect of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, or in any of the foregoing aspects of the 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, the processed oil contains monoglyceryl oleate (MOG) in an amount contributing to about 60 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0419] In the 19th embodiment, the processed oil has a fatty acid profile, the fatty acid profile of the processed oil is substantially the same as that of the pre-processed oil before the processed oil is produced, and the processed oil contains more than 50 wt% of monoacylglycerol (MAG) based on the total weight of the processed oil.

[0420] In the 20th embodiment, the food contains the processed oil of any of the 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment, or any of the foregoing aspects of the 5th, 6th, 7th, 8th, 9th, 10th, 11th, 12th, 13th, or 14th embodiment.

[0421] In the 21st embodiment, the processed oil contains more than 50 wt% of monoacylglycerol (MAG) based on the total weight of the processed oil and has a total fatty acid content.

[0422] In the 22nd embodiment, the processing oil contains more than 60% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil and has a total fatty acid content.

[0423] In the 23rd embodiment, the processing oil contains more than 70% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil and has a total fatty acid content.

[0424] In the 24th embodiment, the processing oil contains more than 80% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil and has a total fatty acid content.

[0425] In the 25th embodiment, the processing oil contains more than 90% by weight of monoacylglycerol (MAG) based on the total weight of the processing oil and has a total fatty acid content.

[0426] In one aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processing oil further contains oleic acid in an amount of about 5% to about 75% of the total fatty acid content of the processing oil.

[0427] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processing oil further contains oleic acid in an amount of about 10% to about 75% of the total fatty acid content of the processing oil.

[0428] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processing oil further contains oleic acid in an amount of about 20% to about 75% of the total fatty acid content of the processing oil.

[0429] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processing oil further contains oleic acid in an amount of about 30% to about 75% of the total fatty acid content of the processing oil.

[0430] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processing oil further contains oleic acid in an amount of about 40% to about 75% of the total fatty acid content of the processing oil.

[0431] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid in an amount of about 50 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0432] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid in an amount of about 60 wt% to about 75 wt% of the total fatty acid content of the processed oil.

[0433] In an aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, or in any of the foregoing aspects of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains linoleic acid in an amount of about 1.5 wt% to about 90 wt% of the total fatty acid content of the processed oil.

[0434] In an aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, or in any of the foregoing aspects of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains linoleic acid in an amount of about 10 wt% to about 25 wt% of the total fatty acid content of the processed oil.

[0435] In an aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, or in any of the foregoing aspects of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains linolenic acid in an amount of about 0.1 wt% to about 2 wt% of the total fatty acid content of the processed oil.

[0436] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linoleic acid, and the ratio of oleic acid to linoleic acid is about 0.01 to 5.

[0437] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linoleic acid, and the ratio of oleic acid to linoleic acid is about 1 to 4.

[0438] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linoleic acid, and the ratio of oleic acid to linoleic acid is about 3 to 4.

[0439] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linolenic acid, and the ratio of oleic acid to linolenic acid is about 1 to 100.

[0440] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linolenic acid, and the ratio of oleic acid to linolenic acid is about 10 to 100.

[0441] In another aspect of the 21st, 22nd, 23rd, 24th, or 25th embodiment, the processed oil further contains oleic acid and linolenic acid, and the ratio of oleic acid to linolenic acid is about 10 to 30.

[0442] The foregoing description of specific embodiments of the present disclosure has been presented for purposes of illustration and description. Exemplary embodiments are selected and described in order to best explain the principles of the present disclosure and its practical applications, thereby enabling one of ordinary skill in the art to best utilize the subject matter. Various embodiments with various modifications are contemplated as being suitable for the particular uses intended. Different features and disclosures of the various embodiments within the present disclosure can be combined within the scope of the present disclosure.

Claims

1. 1. A processed oil comprising monoacylglycerols (MAG), diacylglycerols (DAG), and free fatty acids (FFA), wherein MAG comprises from about 30% to about 90% by weight of the total weight of said processed oil, DAG comprises from about 10% to about 30% by weight of the total weight of said processed oil, and FFA comprises from about 5% to about 60% by weight of the total weight of said processed oil, further comprising non-oil components naturally present in said processed oil, wherein said processed oil is substantially free of monochloropropanediol (MCPD).

2. 10. The processing oil of claim 1, further comprising triacylglycerols (TAGs), said TAGs comprising 5 wt% or less of the total weight of said processing oil.

3. 3. The processing oil of claim 1 or 2, wherein the non-oil components comprise an antioxidant.

4. 4. The processing oil of claim 3, wherein the antioxidant is a tocopherol.

5. 3. The processing oil of claim 1 or 2, wherein the non-oil components include vitamins.

6. 3. The processing oil of claim 1 or 2, wherein the non-oil components comprise one or more of ceramide phosphate, monogalactosyl diacylglycerol, phosphatidylmethanol, sitosteryl esters, campestrol esters, sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin.

7. 7. The processed oil of any one of claims 1 to 6, wherein the processed oil is derived from an oil source 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.

8. 7. The processed oil of any one of claims 1 to 6, wherein the processed oil is derived from a combination of two or more of the group consisting of safflower oil, grape oil, milk thistle 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.

9. The processing oil according to any one of claims 1 to 6, wherein the processing oil is derived from algae or fish.

10. 10. The processing oil of any one of claims 1 to 9, wherein the processing oil has a fatty acid content comprising oleic acid, linoleic acid, and linolenic acid.

11. 11. The processed oil of claim 10, wherein the amount of oleic acid is from 10% to about 75% by weight of the total fatty acid content of the processed oil.

12. 12. The processing oil of claim 11, wherein about 50% to about 99% of the oleic acid content is esterified at the sn-1 position.

13. 11. The processed oil of claim 10, wherein the amount of linoleic acid is from 1.5% to about 90% by weight of the total fatty acid content of the processed oil.

14. 11. The processed oil of claim 10, wherein the amount of linoleic acid is from 0.01% to about 2% by weight of the total fatty acid content of the processed oil.

15. A processing oil comprising: mixing a starting oil with a buffer and a first enzyme to produce a first reaction mixture, wherein the starting oil comprises triacylglycerol (TAG) and monochloropropanediol (MCPD), the TAG being in an amount greater than 50 wt.% based on a total weight of the starting oil, the MCPD being present in an amount of about 1.00 mg / kg to about 12.00 mg / kg of MCPD, the starting oil being free of monoacylglycerol (MAG) or being present in an amount less than 5 wt.% based on a total weight of the starting oil, and the first enzyme being capable of hydrolyzing the TAG to free fatty acids (FFAs); reacting the first reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAGs for a first period of time to produce an aqueous phase and a first lipid reaction product comprising FFAs; inactivating the first enzyme in the first lipid reaction product; recovering said first lipid reaction product by removing it from said aqueous phase; combining said first lipid reaction product with food grade glycerol and a second enzyme capable of esterifying FFAs to form a second reaction mixture; reacting the second reaction mixture for a second period of time to produce a second lipid reaction product comprising a lipid oil phase and a glycerol phase; inactivating the second enzyme in the second lipid reaction product; adding salt to the reaction product and separating the lipid oil phase from the glycerol phase; and 13. A processed oil produced from: recovering a lipid oil phase, wherein the lipid oil phase is the processed oil, the processed oil comprising MAG, diacylglycerol (DAG), and free fatty acids (FFA), the MAG being in an amount of about 30% to about 90% by weight based on the total weight of the processed oil, the DAG comprising about 10% to about 30% by weight of the total weight of the processed oil, and the FFA comprising about 5% to about 60% by weight of the total weight of the processed oil, the processed oil being free of TAG or comprising about 0.1% to about 5% by weight of TAG based on the total weight of the lipid oil phase, and the lipid oil phase being substantially free of MCPD.

16. 16. The processing oil of claim 15, wherein the starting oil has a fatty acid content including oleic acid, linoleic acid, and linolenic acid, and the amount of oleic acid, linoleic acid, and linolenic acid in the processing oil is within 10% of the amount of oleic acid, linoleic acid, and linolenic acid in the starting oil.

17. 17. The processing oil of claim 15 or 16, wherein the starting oil comprises one or more naturally occurring non-oil components selected from the group consisting of ceramide phosphate, monogalactosyl diacylglycerol, phosphatidylmethanol, sitosteryl esters, campestrol esters, sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin, and wherein the one or more naturally occurring non-oil components are maintained in the processing oil.

18. 1. A food product comprising a processed oil, a carbohydrate source, and a protein source, the food product having a total weight of at least 25 grams with a caloric density of about 1 kcal to about 5 kcal per gram, the processed oil constituting about 5% to about 75% of the total caloric content, the processed oil having a triacylglycerol (TAG) content of 5% or less by weight based on the total weight of the processed oil, the processed oil having a monochloropropanediol (MCPD) content of less than 0.10 mg / kg, and the processed oil having a fatty acid content including oleic acid, linoleic acid, and linolenic acid.

19. 20. The food product of claim 18, wherein the processed oil has a monoacylglycerol (MAG) content of 30% or more by weight, based on the total weight of the processed oil.

20. 20. The food product of claim 18 or 19, wherein the processed oil has a diacylglycerol (DAG) content of about 10% to about 30% by weight based on the total weight of the processed oil.

21. 21. The food product of any one of claims 18-20, wherein the processed oil has a free fatty acid (FFA) content of about 5% to about 60% by weight, based on the total weight of the processed oil.

22. 22. The food product of any one of claims 18-21, wherein the processed oil comprises non-oil components naturally occurring in the processed oil, the non-oil components comprising one or more of ceramide phosphate, monogalactosyl diacylglycerol, phosphatidylmethanol, cytosteryl esters, campestrol esters, sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin.

23. 23. The food product of any one of claims 18 to 22, wherein the amount of oleic acid is from 10% to about 75% by weight of the total fatty acid content of the processed oil.

24. 24. The food product of any one of claims 18 to 23, wherein from about 50% to about 99% of the oleic acid content is esterified at the sn-1 position.

25. 25. The food product of any one of claims 18 to 24, wherein the amount of linoleic acid is from 1.5% to about 90% by weight of the total fatty acid content of the processed oil.

26. 26. The food product of any one of claims 18 to 25, wherein the amount of linolenic acid is from 0.01% to about 2% by weight of the total fatty acid content of the processed oil.

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