Method for producing monoacylglyceride oil and food containing monoacylglyceride oil

Abstract

Compositions and methods are provided for incorporating processed oils having high monoacylglyceride (MAG) content into products and food products. In particular, methods are provided for producing processed oils with high MAG content.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Application No. 62 / 794,412, filed January 18, 2019, and U.S. Provisional Application No. 62 / 833,558, filed April 12, 2019, the entireties of each of which are incorporated herein by reference in their entirety.

[0002] Technical Field The present invention relates to a method for producing monoacylglyceride oils and food products containing monoacylglyceride oils. [Background technology]

[0003] A chronic deficiency in the secretion of digestive enzymes by the pancreas is called exocrine pancreatic insufficiency (EPI). Without these digestive enzymes, patients with EPI cannot properly digest the 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 with cystic fibrosis. Pancreatic enzyme replacement therapy (PERT) can reduce the effects of EPI, in which an individual takes an enzyme capsule every time they consume food. Traditionally, PERT treatment involves pancreatic enzymes extracted from pig pancreases.

[0004] Lipids are energy-dense compounds and a source of essential long-chain fatty acids. Typically, consumed lipids, which contain a high percentage of triacylglycerides (TAGs), are digested by lipase secreted from the pancreas into free fatty acids (FFAs) and monoacylglycerides (MAGs). Blocking the release of lipase from the pancreas results in very poor digestion of fats and oils containing triacylglycerides. For patients with EPI, this can lead to significant malnutrition, as calories, essential fatty acids, and fat-soluble nutrients are trapped in undigested lipid particles and pass easily through the entire body.

[0005] There is an unmet clinical need for alternative nutritional sources that individuals with EPI can consume without the need for supplementation with PERT.

[0006] Partially hydrolyzed fats and oils in the form of MAG do not require PERT and are easily absorbed by individuals with EPI. MAG oil-based products have been evaluated in clinics as capsule-based dietary supplements. However, to avoid its unpleasant taste, capsules are utilized. 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 are sold as relatively pure products that contain only trace amounts of the contaminating free fatty acids (FFAs), DAG (diacylglycerides) and TAG, and are substantially free of 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 very high energy caloric density that can be consumed by individuals with inefficient or failed digestive systems. In addition to individuals with pancreatic pathology (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. Additionally, individuals with impaired bile function (cholestasis) could 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 are unable to digest (hydrolyze) the fats in the products. To date, no one has formulated lipids into liquid (shakes) and solid (bars) forms suitable for "non-PERT" use. These formulations would be a "Complete Nutrition" source and could meet all the caloric and essential fatty acid requirements of the individual. Liquid nutrition could be in the form of an Oral Nutrition Supplement (ONS) product for enteral feeding products.

[0008] Thus, there is a need for high calorie density foods that can be consumed by individuals with inefficient or impaired digestive systems.The present application describes a method for producing edible enzyme modified oils (EMOs) that are substantially free of TAGs.

[0009] Monochloropropanediol (MCPD) and glycidyl esters are formed during the refining of edible oils. These compounds are toxic to humans and need to be minimized in foods. 3-MCPD is currently classified as a possible human carcinogen (Group 2B) according to the International Agency for Research on Cancer (IARC). Glycidol is classified as probably carcinogenic to humans (Group 2A) by IARC and the US National Toxicology Program. Current standards recommend exposure of less than 2ug / kg body weight per day, which is less than 140ug / day for a 70kg man and only less than 10ug / day for a 5kg (approximately 10lb) infant.

[0010] MCPD compounds were first detected in acid (HCl) hydrolyzed proteins, but in 2008, the presence of MCPD esters was discovered in refined vegetable oils. The problem turned out to be widespread. Many edible oils are processed to remove components that adversely affect appearance, taste, shelf life, safety, and consumer acceptance. Monoacyl and diacylglycerols (MAG and DAG) in the oils can react with chloride ions to produce 3-monochloropropanediol (3-MCPD) esters and glycidyl esters (GE) in the deodorization process.

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

[0012] Estimates of US infant exposure to consumption of 3-MCPD and glycidyl esters in infant formula have recently been reported (J. Spungen et al. Food Additives & Contaminants: Part TA 2018, VOL. 35, NO. 6, 1085-1092). In this analysis, US FDA data on concentrations of 3-MCPD and glycidyl esters (as 3-MCPD and glycidol equivalents, respectively) in small convenience samples of infant formula were used to estimate exposure from consumption of formula by infants aged 0-6 months. Exposure to 3-MCPD and GE based on the average concentrations across all formulas was estimated to be 7-10 and 2 μg / kg body weight / day, respectively. Estimated average exposure from consumption of formula produced by individual manufacturers was 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 edible enzyme modified oils (EMOs) that are substantially free of contaminants such as TAG and MCPD therefore addresses this need.

[0014] Some vegetable oils are rich in oleic acid. These oils have demonstrated health benefits, some of which may be attributed to oleic acid and oils rich in this fatty acid, such as olive oil, almond oil, and canola (rapeseed) 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 "stereo number". [ka]

[0015] Given the health benefits of these oils, there is a need for compositions and methods that can 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 that include processed oil derived from an oil source. In one embodiment, the processed oil includes 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 is free of TAG or includes a TAG content that is 5 wt% or less of the total weight of the processed oil, the processed oil includes non-oil components that are derived from and naturally present in the oil source, and thus no non-oil components are added to the processed oil.

[0017] In some embodiments, the oil source is derived from a source selected from a plant, an animal, a fish, or a mixture thereof. In some embodiments, the oil source comprises an MCPD compound. In these embodiments, the processed oil is substantially free of MCPD compounds.

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

[0019] In some embodiments, the product comprises greater than 1% MAG by weight of the total weight of the product.

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

[0021] The present disclosure is also directed to a food product, in one embodiment, the food product comprises an oil having a caloric 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 product is a processed oil derived from an oil source, the processed oil has a MAG content of 30% or more by weight of the total weight of the processed oil, a DAG content of about 10% to about 30% by weight of the total weight of the processed oil, and an FFA content of about 5% to about 60% by weight of the total weight of the processed oil, the processed oil is free of TAG or has a TAG content that is about 5% or less by weight of the total weight of the processed oil, and the processed oil is derived from and includes non-oil components naturally occurring in the oil source, such that no non-oil components are added to the processed oil.

[0023] In some embodiments, the oil source of the food product is derived from an origin selected from a plant, an animal, or a fish.

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

[0025] In some embodiments, the food product comprises greater than 1% MAG by weight of the total weight of the product.

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

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

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

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

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

[0031] In some embodiments, the oil contributes between 5% and 95% of the total caloric content of the food product.

[0032] The present disclosure is also directed to methods for making monoacylglycerol enriched oils. In one embodiment, the method includes combining a starting oil comprising triacylglycerol (TAG) with a buffer and a first enzyme capable of hydrolyzing the TAG to free fatty acids (FFAs) 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 of time to produce an aqueous phase and a lipid (free fatty acid) reaction product, inactivating the first enzyme in the reaction product, and recovering the lipid reaction product, combining the 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 lipid oil phase and a glycerol phase of the reaction product, inactivating the second enzyme in the reaction product, adding 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 a plant, an animal, a marine organism, or a mixture thereof. In some embodiments, the starting oil comprises an MCPD compound, 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 of time is sufficient to hydrolyze at least 94% of the TAG in the starting oil.

[0036] In some embodiments, the first period of time is between about 14 hours and 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 performed at a temperature of about 30°C to about 35°C.

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

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

[0040] In some embodiments, the second period of time is 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 of time 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 of time 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 includes drying the reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of the water from the reaction product.

[0044] In some embodiments, the step of drying the reaction product is carried out at a temperature between 20°C and 30°C.

[0045] In some embodiments, the drying step is applied for the entire second period of time.

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

[0047] In some embodiments, the heating is 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 percent sodium chloride by weight.

[0050] In some embodiments, the method further comprises re-establishing a nitrogen atmosphere over the lipid reaction product prior to combining the lipid reaction product with food grade glycerol and a second enzyme capable of esterifying FFAs and glycerol.

[0051] In some embodiments, prior to performing the step of recovering the lipid reaction products, the steps of removing at least a portion of the aqueous phase, replacing at least a portion of the aqueous phase with about an equal amount of water, and waiting a second period of time are 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, the processed oil having a total fatty acid content comprises monoglyceride oleate (MOG) in an amount contributing from about 5% to about 75% by weight 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% monoacylglycerides (MAG) by weight, based on the total weight of the processed oil.

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

[0056] In some embodiments, the processed oil has a total fatty acid content comprising oleic acid and linoleic acid, the linoleic acid being present in an amount of about 10% to about 90% by weight 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% of the amounts of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil is generated.

[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% of each other in the pre-processed oil from which the processed oil is generated.

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

[0061] In some embodiments, a method of treating type II diabetes in a subject in need thereof comprises administering to the subject a composition comprising a processed oil comprising oleic acid monoglyceride, wherein at least 50% by weight of the oleic acid monoglyceride is 1-oleyl monoglyceride.

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

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

[0064] [Figure 1] 1 shows a TLC separation of the components of the starting vegetable oil, the intermediate FFA, and the final MAG oil. [Diagram 2] 1 shows a TLC separation of the components of the starting vegetable oil, the intermediate FFA, and the final MAG oil. [Diagram 3] 1 shows the distribution of FFA, MAG, DAG, and TAG in "Ensure Original Nutritional Shake" and enzyme modified oil products ("GBFS") of the present disclosure. [Figure 4] FIG. 1 shows a block flow diagram of the production process of enzyme modified oil. [Diagram 5] 1 shows the distribution of amino acids and peptides in a ready-to-drink energy drink and GBFS hydrolyzed legume protein. [Figure 6A] The NMR spectrum of standard TAG (tristerol) is shown. [Figure 6B] 1 shows the NMR spectrum of enzyme-modified oil produced from almond oil. [Figure 7] FIG. 1 shows the increase in serum triglycerides following consumption of an EMO-based ready-to-drink shake. [Figure 8] FIG. 1 shows an increase in serum triglycerides following ingestion of a MAG-based RTDS without PERT. [Figure 9] 4 shows the serum glucose levels (mean) of patients after taking MAG-based RTDS without PERT or standard nutritional supplementation with PERT. [Figure 10] 1 shows the mean serum triglyceride levels of patients after taking RTDS on a non-PERT basis or standard nutritional supplementation with PERT. [Figure 11]1 shows the percentages of selected fatty acids in the canola oil and canola EMO of Example 13, and two commercially available monoglyceride samples. [Figure 12A] 1 shows the amounts of various compounds in canola oil and canola EMO of Example 14 based on LC / MS / MS analysis. [Figure 12B] 1 shows the amounts of various compounds in canola oil and canola EMO of Example 14 based on LC / MS / MS analysis. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0065] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention as claimed. In this application, unless specifically stated otherwise, the use of the singular includes the plural, and the word "a" or "an" means "at least one," and the use of "or" means "and / or." Furthermore, 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" encompass 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 merely for organizational purposes 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 expressly incorporated herein by reference in their entirety for any purpose. In the event that one or more of the incorporated literature and similar materials defines a term in a manner that contradicts the definition of the term in this application, this application shall control.

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

[0068] Triacylglycerols ("TAGs"), also known as triglycerides, are glycerides consisting of three fatty acid chains covalently attached to a glycerol molecule via ester bonds. TAGs may be classified as having long or medium chain lengths. Long-chain TAGs contain fatty acids with 14 or more carbons, while medium-chain TAGs contain fatty acids with 6-12 carbons. Long-chain TAGs may include ω3 and ω6 fatty acids. Medium-chain TAGs do not contain ω3 or ω6 fatty acids, as they have saturated fatty acids. Long-chain TAGs (LCTs) and medium-chain triglycerides (MCTs) can serve as energy sources.

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

[0070] Monoacylglycerols ("MAG"), also known as monoglycerides, are glycerides consisting of one fatty acid chain covalently attached to a glycerol molecule via an ester bond.

[0071] As used herein, the term "processed oil" refers to a non-natural oil composition that is substantially free of TAGs or has a reduced amount of TAGs relative to pre-modified or pre-processed oils.

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

[0073] As used herein, the term "food" refers to manufactured or non-natural foods. It is understood that the foods referred to herein are manufactured and non-natural in their entirety, but may contain various combinations of natural ingredients that do not occur in nature, or that, if present in nature, do not occur in the relative amounts that are used in foods.

[0074] The terms "patient," "individual," and "subject" are used interchangeably herein to 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 laboratory animals, including but not limited to rodents, including mice, rats, hamsters, and primates, in veterinary applications, and in the development of animal models of disease.

[0075] "Treatment" is an intervention intended to prevent the onset of a disorder or to alter 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 the disorder and those in whom the disorder is to be prevented. In tumor (e.g., cancer) treatment, a therapeutic agent may directly reduce the pathology of tumor cells or may make tumor cells more susceptible to treatment with other therapeutic agents (e.g., radiation therapy and / or chemotherapy).

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

[0077] In some embodiments, the starting oil may include, by way of example and not limitation, an oil of vegetable origin (such as olive oil, almond oil, canola oil, coconut oil, cottonseed oil, coconut shell oil, coconut olein oil, coconut stearin oil, peanut oil, linseed oil, sunflower seed oil, corn oil, grape seed oil, palm oil, soybean oil, etc.), or an oil of animal origin (such as fish oil, sardine oil, or anchovy oil, or algae oil), or a mixture of any of the above vegetable oils and / or animal oils. In one aspect, the starting oil comprises a blend of olive oil, sunflower seed oil, and linseed oil, wherein about 50% to about 80% by weight of the total weight of the starting oil is olive oil, about 10% to about 30% by weight of the total weight of the starting oil is sunflower seed oil, and about 5% to about 20% by weight of the total weight of the starting oil is linseed oil. In another embodiment, about 50% to about 80% by weight of the total weight of the starting oils is olive oil, about 10% to about 30% by weight of the total weight of the starting oils is linseed oil, and about 5% to about 20% by weight of the total weight of the starting oils is sunflower seed oil.

[0078] In some embodiments, the starting oil comprises an MCPD compound. The MCPD compound may 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 that contain an MCPD compound include almond, canola, coconut, corn, cottonseed, grapeseed, olive, palm, coconut shell, palm olein, palm stearin, peanut, soybean, and sunflower.

[0079] In some embodiments, the process for making a product enriched in MAG includes a first step of hydrolyzing TAG. By way of example and not limitation, the hydrolysis of TAG can be carried out by a lipase such as lipase AY (Amano Enzymes, USA Elgin IL, USA), or any non-position specific lipase that cleaves at sn-1, sn-2, and sn-3 positions.

[0080] In some embodiments, the first step of hydrolyzing TAG may be carried out at a temperature of about 30° C. to 35° C. By way of non-limiting example, the first step of hydrolyzing TAG may be carried out at a temperature of 30° C. to 35° C., 31° C. to 35° C., 32° C. to 35° C., 33° C. to 35° C., 30° C. to 34° C., 31° C. to 34° C., 32° C. to 34° C., 33° C. to 34° C., 30° C. to 33° C., 31° C. to 33° C., 32° C. to 33° C., 30° C. to 32° C., 31° C. to 32° C., 30° C. to 31° C., or 30° C., 31° C., 32° C., 33° C., 34° C., or 35° C.

[0081] In some embodiments, the first step of hydrolyzing TAG can be carried out for about 14 hours to 24 hours. By way of non-limiting example, 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 the TAG results in hydrolysis of substantially all of the TAG. By way of example and not limitation, the first step of hydrolyzing the TAG results in hydrolysis of 94%-100%, 95%-100%, 96%-100%, 97%-100%, 98%-100%, 99%-100%, 94%-99%, 95%-99%, 96%-99%, 97%-99%, 98%-99%, 94%-98%, 95%-98%, 96%-98%, 97%-98%, 94%-97%, 95%-97%, 96%-97%, 94%-96%, 95%-96%, or 94%-95% TAG, or at least 94%, 95%, 96%, 97%, 98%, 99%, or 100% TAG.

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

[0084] In some embodiments, the second step of esterification with glycerol to concentrate the MAG oil content results in concentrating the MAG in the product to about 70%-95%. By way of example and not limitation, the MAG oil content may be concentrated 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 may be carried out at a temperature of about 17° C. to 23° C. By way of non-limiting example, esterification with glycerol may be carried out at a temperature of 17° C. to 23° C., 18° C. to 23° C., 19° C. to 23° C., 20° C. to 23° C., 21° C. to 23° C., 22° C. to 23° C., 17° C. to 22° C., 18° C. to 22° C., 19° C. to 22° C., 20° C. to 22° C., 21° C. to 22° C., 17° C. to 21° C., 18° C. to 21° C., 19° C. to 21° C., 20° C. to 21° C., 17° C. to 20° C., 18° C. to 20° C., 19° C. to 20° C., 17° C. to 19° C., 18° C. to 19° C., 17° C. to 18° C., or 17° C., 18° C., 19° C., 20° C., 21° C., 22° C., or 23° C.

[0086] In some embodiments, the second step of esterification with glycerol may be carried out for about 24 hours to 72 hours. By way of example and not limitation, the second step of esterification with glycerol may be carried out for 24 hours to 72 hours, 36 hours to 72 hours, 48 ​​hours to 72 hours, 60 hours to 72 hours, 24 hours to 60 hours, 36 hours to 60 hours, 48 ​​hours to 60 hours, 24 hours to 48 hours, 36 hours to 48 hours, 24 hours to 36 hours, or 24 hours, 30 hours, 36 hours, 42 hours, 48 ​​hours, 54 hours, 60 hours, 66 hours, or 72 hours.

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

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

[0089] The products resulting from the above embodiments generally result in processed oils that are substantially free of MCPD compounds, although starting oils may have greater than 0.30 mg / kg MCPD compounds, and in some cases, from about 1.0 mg / kg to about 12.00 mg / kg. More specifically, the processed oils resulting from the above methods contain less than 100 mg / kg MCPD, including levels that are undetectable by standard assays. As used herein, the term "substantially free" with respect to the amount of MCPD levels in the processed oils of the present invention means levels that are below the detection limit of the assay described in Example 11 below.

[0090] The product obtained from the above embodiment is a processed oil enriched in MAG, specifically 1-MAG (MAG esterified at sn-1 position). In the case of processed oil made from starting oil with oleic acid content, this results in the production of 1-oleyl monoacylglyceride (1-OG). It has been found that the manufacturing process embodiment of the present disclosure can efficiently convert even sn-2 oleic acid TAG to 1-OG. For example, starting from triolein, the manufacturing process embodiment of the present disclosure can obtain three 1-OG molecules from a single triolein molecule, whereas in the digestion of triolein by pancreatic lipase, the lipase can obtain only one-third of the total oleic acid in the form of monoacylglycerol (specifically as 2-monoacylglycerol (2-OG) rather than 1-OG) due to the liberation of the oleic acid moieties at sn-1 and sn-3 positions as free fatty acids. Thus, the processed oil produced by the manufacturing method of the present disclosure can have up to three times the 1-OG content compared to the conventional digestion process. The following reaction schematics show the conversion of triolein to 2-OG and two free oleic acid molecules (Process A - conventional digestion) and the conversion of three molecules of triolein to 1-OG (Process B) by the process of the present disclosure. [ka]

[0091] It has also been found that the manufacturing process embodiment of the present disclosure can preserve the fatty acid profile of the starting oil in the processed oil. Table 2 below shows representative fatty acid profiles of various starting oils and provides the percentage of total fatty acid methyl esters (FAMEs). 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, oil. Table 2 also provides the oleic acid / linoleic acid ratio and oleic acid / linolenic acid ratio of each oil. [Table 2]

[0092] In particular, linoleic acid (an omega-3 fatty acid) and linolenic acid (an omega-6 fatty acid) are known to be essential for humans and can be used to produce longer-chain, more unsaturated fatty acids (otherwise known as long-chain polyunsaturated fatty acids (LC-PUFAs)), including eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA).

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

[0094] In some embodiments, the processing oil comprises a MAG content of 30% or more by weight of the total weight of the processing oil. By way of example and without limitation, the processing oil may comprise a 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%-8 ...80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-90%, 80%-9 ~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% MAG content.

[0095] In some embodiments, including those described above with respect to 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 example and not limitation, the processing oil may comprise a DAG 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 wt% 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 50 wt%, 5 ... The MAG content may be 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% by weight.

[0096] In some embodiments, including those described above with respect to MAG and / or DAG content, the processing oil comprises an FFA content of 5 wt% or more of the total weight of the processing oil. By way of example and not limitation, the processing oil may comprise an FFA content of about 5 wt%-66 wt%, 10 wt%-66 wt%, 20 wt%-66 wt%, 30 wt%-66 wt%, 40 wt%-66 wt%, 50 wt%-66 wt%, 5 wt%-50 wt%, 10 wt%-50 wt%, 20 wt%-50 wt%, 30 wt%-50 wt%, 40 wt%-50 wt%, 5 wt%-40 wt%, 10 wt%-40 wt%, 20 wt%-40 wt%, 30 wt% The MAG content may be about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, or 66% by weight.

[0097] In some embodiments, including those described above with respect to MAG, DAG and / or FFA content, the processing oil is free of TAG or contains a TAG content of 5 wt% or less of the total weight of the processing oil. By way of non-limiting example, the processing oil contains a TAG content of about 0 wt%-5 wt%, 1 wt%-5 wt%, 2 wt%-5 wt%, 3 wt%-5 wt%, 4 wt%-5 wt%, 0 wt%-4 wt%, 1 wt%-4 wt%, 2%-4 wt%, 3 wt%-4 wt%, 0 wt%-3 wt%, 1 wt%-3 wt%, 2 wt%-3 wt%, 0 wt%-2 wt%, 1 wt%-2 wt%, 0 wt%-1 wt%, or 0 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, or 5 wt% of the total weight of the processing oil. By way of further example, and without limitation, the TAG content can 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 about 80 wt% MAG by total weight of the processing oil, about 10 wt% to about 30 wt% DAG by total weight of the processing oil, about 0 wt% to about 5 wt% TAG by total weight of the processing oil, and about 5 wt% to about 60 wt% FFA by total weight of the processing oil.

[0099] In any of the embodiments herein, the processed oil comprises non-oil components that are derived from and naturally present in the oil source, and therefore non-oil components are not added to the processed oil.By way of example and without limitation, such non-oil components may comprise 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 antioxidants are 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, monogalactosyl diacylglycerol, phosphatidylmethanol, sitosteryl esters, campestrol esters, sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin.

[0100] In any of the embodiments herein, the processed oil comprises monoglycerides of oleic acid (MOG) and has a total fatty acid content. The MOG can contribute about 5% to about 75% by weight of the total fatty acid content of the processed oil. In some embodiments, by way of example and not limitation, the MOG can contribute about 10% to about 75% by weight, about 20% to about 75% by weight, about 30% to about 75% by weight, about 40% to about 75% by weight, about 50% to about 75% by weight, or about 60% to about 75% by weight of the total fatty acid content of the processed oil. In some embodiments, the processed oil comprises oleic acid in an amount between about 5% and about 75% by weight of the total fatty acid content of the processed oil. In some embodiments, by way of example and not limitation, oleic acid can contribute from about 10% to about 75% by weight, from about 20% to about 75% by weight, from about 30% to about 75% by weight, from about 40% to about 75% by weight, from about 50% to about 75% by weight, or from about 60% to about 75% by weight of the total fatty acid content of the processed oil.

[0101] In any of the embodiments herein, the processed oil comprises MOG, the MOG comprising at least 50% by weight of 1-oleyl monoglyceride (1-OG) of the total amount of MOG. By way of example and without limitation, the processed oil may comprise at least 50%, at least 60%, at least 70%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 99% 1-OG of the total amount of MOG.

[0102] In any of the embodiments herein, the processed oil comprises oleic acid in an amount of about 10% to about 75% by weight of the total fatty acid content of the processed oil. By way of example and not limitation, oleic acid may be present in an amount of about 10% to about 75% by weight, about 20% to about 75% by weight, about 30% to about 75% by weight, about 40% to about 75% by weight, about 50% to about 75% by weight, about 60% to about 75% by weight, about 10% to about 20% by weight, about 10% to about 30% by weight, about 10% to about 40% by weight, about 10% to about 50% by weight, or about 10% to about 60% by weight of the total fatty acid content of the processed oil. In any of the embodiments herein, the oleic acid is esterified at the sn-1 position. By way of example and not limitation, the processed oil may 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 herein, the processed oil comprises linoleic acid in an amount of about 1.5% to about 90% by weight of the total fatty acid content of the processed oil. By way of example and not limitation, linoleic acid may be present in an amount of about 10% to about 90% by weight, about 20% to about 90% by weight, about 30% to about 90% by weight, about 40% to about 90% by weight, about 50% to about 90% by weight, about 60% to about 90% by weight, about 70% to about 90% by weight, about 80% to about 90% by weight, about 10% to about 25% by weight, or about 10% to about 20% by weight of the total fatty acid content of the processed oil. In some embodiments, the processed oil comprises 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 herein, the processed oil comprises linoleic acid in an amount of about 0.01% to about 2% by weight of the total fatty acid content of the processed oil. By way of non-limiting example, linoleic acid may be present in an amount of about 0.1 to about 2% by weight, about 0.5 to about 2% by weight, about 1% to about 2% by weight, or about 1.5% to about 2% by weight of the total fatty acid content of the processed oil. In some embodiments, the processed oil comprises oleic acid and linoleic acid, and the ratio of oleic acid to linoleic acid is about 1 to about 100. By way of example, but not limitation, the ratio of oleic acid:linolenic acid may 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. References to fatty acids in the claims should not be understood as being limited to only free fatty acids, but may refer to fatty acids in glyceride form. In the processed oils of the present disclosure, the fatty acids are primarily in MAG form, and in pre-processed 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 processed oils, the free fatty acids are typically less than 10%.

[0105] In any of the embodiments herein, 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.By way of example and not limitation, the fatty acid profile of the processed oil may 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 comprises oleic acid, linoleic acid, and linoleic acid.However, any combination of fatty acids may form the fatty acid profile.By way of example and not limitation, the fatty acid profile may comprise any combination of the fatty acids listed in Table 2, as well as EPA and DHA.

[0106] In any of the embodiments herein, the processed oil contains three times the amount of MAG molecules compared to the number of TAG molecules in the pre-processed oil from which the oil is generated. 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 example and not limitation, 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 three 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 up to three oleic acid moieties are converted to three oleic acid MAG, such as triolein. In some embodiments, the amount of MAG in the processed oil is three times the amount of TAG in the pre-processed oil from which the processed oil is generated. For example, the number of MAGs generated corresponds to about three times the number of TAGs in the pre-processed oil. In some embodiments, the processed oil contains about the same amount of oleic acid in the form of oleic acid monoglyceride as in the pre-processed oil from which the processed oil was produced.

[0107] In some embodiments, the product or food product may contain at least 1% MAG. By way of example and not limitation, the food product may contain at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50% or more by weight of the product or food product, or any range or amount therebetween. By way of further example and not limitation, the product or food product may contain 5% to 15% MAG by weight of the total weight of the product or food product.

[0108] In some embodiments, the product or food product may comprise at least 3% by weight of the total weight of the product or food product of any of the processed oils of the embodiments herein.By way of example and not limitation, the food product may comprise at least 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% or more by weight of the processed oil of any of the embodiments herein of the product or food product, and any range or amount therebetween.

[0109] In some embodiments, the food product may further comprise a carbohydrate source. By way of example and not limitation, such carbohydrate sources may include simple sugars such as glucose and fructose derived from carbohydrate sources such as fruit and agave syrup. Other carbohydrate sources include other plant-based liquid sugars, starches, and sugar alcohols.

[0110] In some embodiments, the food product may further comprise a protein source. In certain aspects, the protein source may be hydrolyzed or partially hydrolyzed. By way of example and not limitation, such protein sources may include milk proteins (casein and whey) and other plant proteins including proteins from soy, rice and rice bran, lentils, chickpeas, peanuts, almonds, spirulina (algae), quinoa, mycoprotein, chia seeds and hemp seeds. The hydrolyzed proteins may be extensively hydrolyzed, and legume proteins are enriched in peptides of 1-10 amino acids in length. In some embodiments, the proteins are enriched about 25%-75% in peptides of 1-10 amino acids in length compared to commercially partially hydrolyzed proteins and other whey-based hydrolysates such as Peptamen and Crucial. By way of non-limiting example, the protein may be enriched in peptides of 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 product may be liquid, semi-solid, or solid. By way of example and not limitation, semi-solids may include products such as puddings, mousses, pops, or ice cream. By way of example and not limitation, liquids may be shakes or other drinks. By way of example and not limitation, solids may be bars or other solid foods.

[0112] In some embodiments, the product or food product further comprises a viscosity modifier. The viscosity modifier may be, for example, but not limited to, xanthan gum or acacia gum. In some embodiments, the product or food product may further comprise a structure or stability improving ingredient, for example, but not limited to, gum arabic, sunflower lecithin and xanthan gum. In some embodiments, the product or food product may further comprise a fiber source, for example, but not limited to, oligosaccharides. In some embodiments, the product or food product may further comprise a food preservative, for example, but not limited to, sodium benzoate or potassium sorbate.

[0113] In some embodiments, the product or food product further comprises a flavor, masker, or blocker. By way of example and without limitation, the flavor may 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 example and not limitation, 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 about 25 grams to about 3000 grams. By way of example and not limitation, the food product can have a weight of 25 grams to 3000 grams, 25 grams to 2500 grams, 25 grams to 2000 grams, 25 grams to 1000 grams, 25 grams to 500 grams, 50 grams to 3000 grams, 50 grams to 2500 grams, 50 grams to 2000 grams, 50 grams to 1500 grams, 50 grams to 1000 grams, 50 grams to 500 grams, 100 grams to 3000 grams, 100 grams to 25 00 grams, 100 grams to 2000 grams, 100 grams to 1500 grams, 100 grams to 1000 grams, 100 grams to 500 grams, 250 grams to 3000 grams, 250 grams to 2500 grams, 250 grams to 2000 grams, 250 grams to 1500 grams, 250 grams to 1000 grams, 250 grams to 500 grams, 500 grams to 3000 grams, 500 grams to 2500 grams, 500 grams ~2000 grams, 500 grams~1500 grams, 500 grams~1000 grams, 1000 grams~3000 grams, 1000 grams~2500 grams, 1000 grams~2000 grams, 1000 grams~1500 grams, 1500 grams~3000 grams, 1500 grams~3000 grams, 2000 grams~3000 grams, 2000 grams~2500 grams, 25 grams~250 grams, 50 grams~250 grams The lamb may have a weight of 100 grams to 250 grams, 25 grams to 100 grams, 50 grams to 100 grams, 25 grams to 50 grams, or a total weight of up to 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.

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

[0116] In some embodiments, about 20%-75% of calories in the food product are derived from oil or fat. In one aspect, the oil or fat is a processed oil according to any of the embodiments herein. In yet another aspect, the processed oil has a MAG content of 30% or more by weight of the total weight of the processed oil. In another aspect, the processed oil has a MAG content of about 40% to about 99% by weight of the total weight of the processed oil. In yet another aspect, the processed oil has a TAG content of less than 5% by weight of the total weight of the processed oil. Examples, without limitation, include 20%-50%, 30%-50%, 40%-50%, 20%-40%, 30%-40%, 20%-30%, 20%-75%, 30%-75%, 40%-75%, 50%-75%, 60%-75%, 70%-75%, 20%-70%, 30%-70%, 40%-70%, 50%-70%, 60%-70%, 20%-60%, 30%-60%, 40%-60%, 50%-60%, or about 20%, 21%, 22%, 23%, 24%, 25%, 26%, 28%, 29%, 30%-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 ... %, 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% are derived from any of the processing oils set forth above.

[0117] In any of the above embodiments relating to a food product, about 20%-50% of the calories of the food product are derived from a carbohydrate source. By way of non-limiting example, 20%-50%, 30%-50%, 40%-50%, 20%-40%, 30%-40%, 20%-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 product are derived from a carbohydrate source.

[0118] In any of the above embodiments relating to food products, about 10% to 50% of the calories of the food product are derived from a protein source. Examples, without limitation, include 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%, 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%, 75%, 76%, 77%, 78%, 79%, 80%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%, 100%, 100%, 100%, 1 %, 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% is derived from a protein source.

[0119] It should be understood that the above disclosed embodiments of the food products may be combined.

[0120] In some embodiments, the food products of this disclosure comprise the processed oil of this disclosure.

[0121] In some embodiments, the EMO-based product is consumed by an individual with a dysfunctional digestive system, for example, but not limited to, an individual suffering from EPI, or an individual utilizing PERT with food. In some embodiments, the EMO-based product is consumed by an individual who desires a faster or more complete conversion of lipids to serum triglycerides. Thus, a method is provided for feeding a human or animal subject with a dysfunctional digestive system. The method comprises administering to the patient a food product according to any of the above 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 cholestasis.

[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 diabetes 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 diabetes is type II diabetes. EXAMPLES

[0124] Example 1: Process for making a product enriched in MAG compared to a TAG-rich starting oil. The method to create a product enriched in MAGs compared to a TAG-rich starting oil involves three key steps: (1) mild enzyme-catalyzed reactions: sequential hydrolysis of triglycerides (TAGs) to convert the native oil into a specific combination of FFAs, MAGs, DAGs, and low residual TAGs, (2) esterification with glycerol: producing mainly high amounts of MAGs and leaving low concentrations of FFAs, and (3) isolation of the modified lipid products: this is achieved by phase separation with or without the aid of centrifugation.

[0125] Step 1. Enzymatic conversion of triacylglycerol Buffer preparation. 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 the mixing vessel, the agitator was set at 200 RPM, and 0.213 kg of citric acid (anhydrous) was added. After the powder was dissolved, the pH was adjusted to pH=5.8 with sodium hydroxide solution (approximately 0.121 kg). 220 mL was removed for subsequent enzyme preparation.

[0126] Preparation of Enzyme Solution: In a separate 250 mL bottle, the enzyme solution was prepared with gentle stirring. 200 mL of citrate buffer was placed in the mixing vessel. 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 vessel to give a total of 10 kg of vegetable oil mixture. A vacuum was applied to reduce the pressure to about 20 mmHg to degas the material (particularly from any dissolved oxygen). Agitation was set to 200 RPM and the mixture was heated to 33° C. and stirred for about 15 minutes to remove any dissolved gases. The vacuum was then replaced with a nitrogen gas atmosphere. Once the mixture was well dispersed, 220 mL of the enzyme preparation in buffer was added. Stirring was continued and the reaction was monitored for 24 hours until conversion to FFAs was complete based on TLC analysis.

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

[0129] Agitation was stopped and the phases were allowed to separate for approximately 60 minutes.

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

[0131] Step 2. Esterification with glycerol. Typically, re-esterification of FFAs with glycerol produces a mixture of MAGs, DAGs and TAGs. We found that by significantly lowering the temperature (below 25° C.) and removing (by evaporation) the water formed during the reaction, the proportion of MAGs 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 (approximately 10 L) was cooled to approximately 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 approximately 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 the water was collected with a receiver in place. Once the residual water had stopped evaporating, 20 g of Amano Lipase G dissolved in water (50 mL) was added to the reactor. The temperature was reduced to 23° C. and the vacuum was changed to 5 mmHg using an oil diaphragm pump and cold trap to collect the water. The mixture was stirred under vacuum at 300 RPM at 23° C. for 72 hours, at which point the vacuum was broken and the mixture was blanketed with nitrogen gas. The mixture was analyzed after 72 hours using TLC to assess the conversion to MAG, as shown in FIG. 1.

[0133] Step 3. Lipase inactivation and phase separation. After the reaction was complete, the lipase was inactivated by heating the mixture (under a nitrogen gas blanket) to 70° C. for 1 hour. At this point, the MAG oil and glycerol are well mixed and very difficult to separate by traditional gravity or centrifugation methods. After considerable experimentation, it was found that the lipids could be separated from the excess glycerol by adding 0.3 wt. % salt (NaCl) to the reaction mixture under stirring. The product mixture was then cooled to about 60° C. and left without stirring for about 1 hour.

[0134] The lipid oil phase was separated from the remaining heavier glycerol phase. The glycerol phase was removed. It contains some salts, residual water, and dissolved inactivated enzymes (contained in the visible interface). The glycerol phase can be reused after membrane filtration and should 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) is ready for immediate use or can be stored under nitrogen blanket.

[0135] Product Storage: The final hydrolysate was transferred to food grade containers with nitrogen gas overlay for storage and transport.

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

[0137] Thin-layer chromatography studies. Components of oil samples were separated using TLC plates (Analtech Uniplate Silica Gel GHL, with inorganic binder, 20 × 20 cm, 250 μm). The solvent was a hexane:diethyl ether:acetic acid (70:30:1) solution. Typical sample size was 3 μL. After the solvent front had moved near the top of the plate (approximately 1 cm), the plate was removed from the TLC tank and the solvent was allowed to evaporate in a fume hood. Components were visualized with iodine vapor (at room temperature) in the TLC tank and relative intensity was estimated by colorimetric imaging (Amersham 600 Imager). After 15 min in the tank, the plate was removed and photographed. After 30–60 min, the intensity of the spots decreased.

[0138] Physical property determinations were performed to establish product consistency, color, moisture content, fat and oil (miscibility).

[0139] Figure 1 shows the end result of steps 1-3 in the process of making 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, the tocopherol spot can be seen tracking above the TAG spot in all three lanes.

[0140] Fatty acid profile study - gas chromatography. 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 alpha-linolenic acid, which were analyzed after derivatization as fatty acid methyl esters and compared with standards. For derivatization, samples (500 μl) were 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 tridecanoic acid internal standard solution (10 mg / ml). The reaction tube was vortexed and incubated in a 60 °C heat block for 30 min.

[0141] The reaction tube was removed from the heat block and allowed to cool for 15 minutes. The reaction was then quenched by adding 1 ml of distilled water, followed by 1 ml of hexane. The reaction tube was vortexed for 60 seconds and the phases were allowed to separate for 3 minutes. The 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] Samples were analyzed using an Agilent 7890A Gas Chromatograph with a Flame Ionization Detector and Agilent Openlab CDS Chemstation software. GC column: Omegawax 100 (15m x 0.1mm x 0.1um) column. Results were converted to weight percent 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. % of FFA, MAG, DAG, and TAG in oil as determined by thin layer chromatography.

[0144] Example 3: Another example of a process to make a product enriched in MAGs compared to a starting oil rich in TAGs. The following steps are illustrated by the block flow diagram of FIG.

[0145] The vegetable oil was added to citric acid and sodium hydroxide (caustic) in DI water and heated to 33°C + / - 2°C. A slight vacuum was applied to degas and remove oxygen. Lipase AY was added. Hydrolysis of the mixture was carried out under a nitrogen blanket at a temperature of 33°C + / - 2°C for 14-24 hours.

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

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

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

[0149] Example 4: Ready-to-Drink Formulation Incorporating MAG and Hydrolyzed Proteins The products of the present disclosure were manufactured as conventional "milkshake" formulations 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 are as follows: Water, Organic Agave Syrup, Hydrolyzed Pulse 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-Pantotinate, Pyrodoxine Hydrochloride, Thiamine Hydrochloride, Riboflavin, Vitamin D3, Folic Acid, Cyanocobalamin, Vitamin K2.

[0150] Carbohydrates were supplied as simple sugars (glucose and fructose) from fruit and agave syrup.

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

[0152] We also generated extensively hydrolyzed pulse proteins (EHPs) containing peptides in a more bioavailable size range for transport across the intestinal wall. EHPs were generated by further enzymatic hydrolysis. For example, partially hydrolyzed pulse protein (Puris Pea Protein 870H, described above) protein was dissolved in 100 mM phosphate buffer at a concentration of 25 mg / ml. Enzymes were added and the reaction was incubated overnight at 50°. Three different commercially available GRAS enzymes were evaluated: Alcalase, Thermoase, and Flavorzyme.

[0153] The average size and distribution of peptides in protein samples were assessed using size exclusion chromatography. Samples were dissolved at a concentration of 25 mg / ml in 100 mM phosphate buffer, pH 6.8, and analyzed on a Shimadzu HPLC 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 room temperature, flow rate of 0.8 mL / min). Samples were compared to molecular weight standards (Phenomenex SEC standard partial ALO-3042). Size was estimated using a calibration curve generated from known molecular weight standards. The average size of unhydrolyzed pulse proteins was approximately 200 amino acids. The average size of Puris Pea 870H partial hydrolysates 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 a ready-to-drink beverage nutritional drink (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 pulse 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 (X-axis) of the present disclosure. The average size of GBFS EHP is 3-4 amino acids, mostly 1-7 amino acids.

[0155] The fat was provided in the form of the reconstituted lipid MAG, made from a blend of olive oil (70%), sunflower oil (21%) and flaxseed oil (9%) to provide the energy and other benefits of polyunsaturated fatty acids (PUFAs), ω6 PUFAs and ω3 PUFAs, with an ω6 to ω3 ratio of approximately 4:1.

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

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

[0158] The nutritional information for the prototype product is shown in Table 3. In Table 3, **Percent Daily Value (DV%) is based on a 2,000 calorie diet. †Daily Value (DV) not established. [Table 3] TIFF0007654550000006.tif51139

[0159] Sensory testing. The FFA produced from the vegetable oil blend was found by the taste panel to be unpalatable. Surprisingly, the MAG oil produced from this blend was palatable and similar in taste and texture to the original triglyceride oil. When the MAG oil was formulated into the RTDS product described above, the flavor was acceptable and indistinguishable from a similar commercial product with intact (undigested) lipids and proteins.

[0160] Example 5: Production of multiple batches of EMO The timing of the process described in Example 1 to produce EMO was evaluated and produced oil with MAG > 70%, MAG + FFA > 85%, and TAG < 5%.

[0161] Table 4 shows a scan of a TLC plate showing the concentrations of MAGs and FFAs in enzyme-modified EMO produced from a blend of olive / linseed / sunflower oil (7:2:1 ratio). In these experiments, step 2 was extended to 84 h to establish upper timing and temperature limits to avoid the formation of TAGs. [Table 4]

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

[0163] Example 6: Evaluation of TAG-free enzyme-modified almond oil by NMR analysis. TAG-free EMO was produced using almond oil. Reaction conditions were as described in Example 1. Step 2 was 72 hours to minimize the production of TAG.

[0164] Figures 6A-6B show the results of EMO synthesis from almond oil. 13 FIG. 6A shows the C-NMR analysis of the standard TAG (tristerol). 13 Figure 6B shows the C-NMR signal and the characteristic peaks at 62.173 ppm and 68.921 ppm of EMO. 13 C-NMR signals are shown, showing the absence of a discernible TAG signal. The integration of the actual signals indicates that the distribution of acylglycerols between MAG:DAG is 88%:12%. The samples were analyzed on a JEOL model ECA600II NMR spectrometer operating at 600 MHz proton and 150 MHz carbon. Samples were prepared in 5 mm tubes and run at ambient temperature, locked in CDCl3.

[0165] Example 7: Clinical Trial of EMO-Based Ready-to-Drink Shake The study was designed to show that patients with EPI could consume food made with the TAG-free oil produced by the inventors without taking enzyme supplements and still absorb serum lipids and generate TAG.

[0166] The clinical trial was a single-center, randomized, double-blind, crossover study evaluating an EMO-based ready-to-drink shake (RTDS) on blood lipid levels, safety, tolerability, and mouthfeel compared to a standard dietary supplement used concomitantly with Pancreatic Enzyme Replacement Therapy capsules ("PERT").

[0167] Inclusion criteria for the trial included: 1. Provision of a signed and dated informed consent form. 2. Demonstrate willingness to comply with all study procedures and availability for the duration of the study. 3. Male or female, 12 years of age or older. 4. Diagnosis of CF. 5. Currently receiving treatment with an over-the-counter pancreatic enzyme product for ≥3 months. 6. Clinically stable with no evidence of acute respiratory illness within 1 month of enrollment. 7. Stable weight (defined as not having lost more than 5% weight within 3 months of enrollment). 8. Women of childbearing potential must agree to continue using medically acceptable contraception throughout the study and for 30 days immediately following the last dose of study drug. Medically acceptable contraception includes bilateral tubal ligation or contraceptive implant, contraceptive injection (Depo-Provera™), intrauterine device, or oral contraceptive 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 dual-barrier method consisting of a combination of any two of the following: diaphragm, cervical cap, condom, or spermicide. 9. Ability to take oral medications and oral liquid nutritional supplements, and willingness to adhere to the study intervention. 10. Agreement to adhere to lifestyle considerations (see section 5.3) for the duration of the trial.

[0168] Exclusion criteria for the trial included: 1. Evidence of cardiovascular, respiratory (excluding underlying conditions), genitourinary, gastrointestinal / hepatic (excluding underlying conditions), hematological / immunological, head, ear, eye, nose, throat, dermatological / connective tissue, musculoskeletal, metabolic / nutritional (excluding underlying conditions), endocrine (excluding controlled diabetes mellitus), neurological / psychiatric, allergy (to milk, nuts, or soy), recent major surgery, or other relevant disease (as revealed by medical history, physical exam, and / or laboratory tests) that may limit participation in or completion of the study. 2. History of acute abdominal disease within the past year. 3. History of fibrosing colon disease. 4. History of distal intestinal obstruction syndrome (DIOS) within 6 months prior to enrollment. 5. Solid organ transplant or surgery affecting the large intestine other than appendectomy. 6. Small bowel surgery that significantly affected absorptive capacity (e.g., gastrectomy or pancreatectomy). 7. Inflammatory bowel disease, including chronic diarrheal disease, not related to pancreatic insufficiency. 8. Celiac or Crohn's disease. 9. Receiving enteral tube feeding for more than 50% of daily caloric intake. 10. Pregnant or breastfeeding. 11. Malignancy of any kind involving the gastrointestinal tract within the past 5 years. 12. Known allergy to pancreatin or to any of the inactive ingredients (excipients) in pancreatin capsules. 13. Suspected non-compliance or non-cooperation. 14. Taking any experimental medication within 30 days prior to starting the trial. 15. Psychiatric disorder or any other lack of fitness which, in the opinion of the investigator, precludes the subject's ability to participate in or complete the clinical trial. 16. Diagnosis of human immunodeficiency virus in medical history. 17. Lung or other solid organ transplant or documented forced expiratory volume (FEV) ≤ 25%. 18. Use of lipid-lowering therapy, including statins, fibrates, niacin, and proprotein convertase subtilisin kexin type 9 (PCSK9) inhibitors, that could not be taken for at least 14 days prior to Study Day 1 through Study Day 15. Patients were male or female aged 12 years or older with a diagnosis of cystic fibrosis. Patients were also currently receiving treatment with an over-the-counter pancreatic enzyme product for 3 months or more and were in clinically stable condition with no evidence of acute respiratory illness within 1 month of enrollment.

[0169] Patients visited the clinic after an overnight fast and a standardized dinner. Patients in arm 1 (10 patients) received RTDS with PERT placebo, and patients in arm 2 (10 patients) received standard nutritional supplements with PERT. Serial blood samples over 6 hours (0, 1, 2, 3, 4, 5, 6 hours) were obtained from patients in both study arms without repeated provision of RTDS or standard nutritional supplements. Water was available for consumption 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 received standard nutritional supplements with PERT, and patients in arm 2 received RTDS with PERT placebo. Serial blood samples over a 6-h period (0, 1, 2, 3, 4, 5, 6 h) were obtained from patients in both study arms without repeated provision of RTDS or standard nutritional supplements.

[0171] The standard dietary supplement 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, gum acacia, 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-alpha tocopheryl acetate, ascorbic acid, potassium chloride, ferrous sulfate, zinc sulfate, niacinamide, calcium pantothenate, manganese sulfate, copper sulfate, pyridoxine hydrochloride, thiamin hydrochloride, beta-carotene, vitamin A palmitate, riboflavin, folic acid, chromium chloride, biotin, potassium iodide, phytonadione, sodium selenite, sodium molybdate, vitamin D3, and vitamin B12.

[0172] The RTDS contained the following: water, organic date syrup, enzyme modified almond oil, enzyme hydrolyzed pulse protein, soluble corn fiber, cocoa powder, natural flavors, 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, and vitamin B12 (cyanocobalamin).

[0173] The dietary supplement was 5.9% fat, 5.9% protein, and 19% carbohydrate by weight, and the RTDS was 7.4% fat, 4.7% protein, and 9.8% carbohydrate by weight.

[0174] The lipid dose was 0.5 g / kg body weight. The lipid in the standard supplement was a blend of TAG derived from canola oil, high oleic sunflower oil, and corn oil. In the intervention drink, MAG was produced from almond oil. The lipid dose for each patient was based on well-established "lipid tolerance tests", which are similar in design and scope to glucose tolerance tests. The recommended dose for these tests is 0.5-1.0 g / kg, administered over 20-30 minutes. Samples were taken at the start of the study and every hour for 6 hours. Serum triglyceride levels were measured using standard laboratory methods.

[0175] The PERT dose used in this study followed the manufacturer's recommended dosing guidelines (2,500 IU of lipase activity per gram of ingested fat), which corresponds to 3–4 capsules during the crossover phase of the study.

[0176] FIG. 7 shows the increase in serum triglycerides after ingestion of an EMO-based ready-to-drink shake in two patients. In FIG. 7, the dashed line represents the patient who received 0.5 g / kg body weight of enzyme-modified almond oil, and the solid line represents the patient who received 0.5 g / kg body weight of canola oil, high oleic sunflower oil, and corn oil, which were incorporated into the RTDS and consumed over a half hour period. FIG. 7 shows that the enzyme-modified oils in the RTDS were 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 serum triglycerides after ingestion of the MAG-based RTDS without PERT, and the solid line represents standard of care RTDS with PERT. Patients received 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, the absorption of lipids and their conversion to serum triglycerides was significantly faster after ingestion of the MAG-based RTDS without PERT than the TAG-based (standard of care) product with PERT. This suggests that the patient suffered from cholestasis (disruption of bile flow from the liver) in addition to EPI, and not just a lack of sufficient enzymes, so that the canola oil, high oleic sunflower oil, and corn oil in the standard care drink could not be adequately emulsified. The oils need to be emulsified into very small droplets to generate the surface area required for pancreatic lipase to hydrolyze the oils into MAG and FFAs that are transported to the enterocyte. This activity requires bile acids from the liver. The TAG in the standard care drink could not be emulsified into the microemulsions required for optimal lipase activity in the small intestine, so serum triglycerides did not increase as quickly as with the MAG formulation, which does not require lipase activity.

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

[0180] The sugar intake of a hypothetical 65 kg patient in the trial is shown below in Table 5 for the standard nutritional supplement and the RTDS. Most of the sugar and carbohydrate in the control drink is starch or starch, which is easily converted to glucose. In the trial drink, the amount of drink that the hypothetical 65 kg patient would consume is less (the trial drink has a higher concentration of lipids), and the carbohydrates are provided in smaller amounts as a 50:50 mix of fructose and glucose. Therefore, less glucose is actually consumed. [Table 5]

[0181] FIG. 9 shows the increase in serum glucose, averaged from eight patients from each of arms 1 and 2 in the trial, over a six-hour sampling period. Patients consuming RTDS showed a notable decrease in maximum postprandial serum glucose, remaining below the standard supplement cohort. These results indicate that an EMO-based supplement with more 1-monoacylglycerol, such as 1-oleylmonoglycerol, was able to positively impact glucose homeostasis, compared to standard supplementation with PERT, which is expected to generate only small amounts of 2-monoacylglycerol, such as 2-oleylmonoglycerol. Based on the amount of glucose administered, higher serum glucose levels were expected for the RTDS cohort, and the effect shown is unexpected.

[0182] Figure 10 shows serum triglyceride levels averaged from eight patients from each of arms 1 and 2 in the trial over a six hour sampling period. Both the test and control groups showed similar triglyceride levels, indicating that patients absorbed the same amount of lipids from either the standard dietary supplement with PERT or the RTDS without PERT.

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

[0185] The method can also be used to produce high calorie products in semi-solid form such as puddings, mousses, "pops", and ice cream-like products using beverage-based recipes and adding viscosity modifiers such as xanthan gum and acacia gum.

[0186] Table 6 shows the main components and nutritional value of high-calorie (1.5 kcal / mL) RTDS. [Table 6] TIFF0007654550000010.tif11154

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

[0188] Example 9: High Calorie, PERT-Free Bar High calorie bars can be prepared as follows: Add DI water (approximately 60% of final volume) to main mixing vessel and heat to approximately 60°C. Mix in hydrolyzed protein, then add agave syrup. In a separate vessel, combine warm (60°C) EMO and lecithin with a hand mixer. Once lecithin is dissolved, add EMO / lecithin to water phase and mix. Add additional water to final weight (volume).

[0189] Table 8 shows the main ingredients and nutritional value of the high calorie PERT-free bar. [Table 8]

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

[0191] Example 10: Preparation of ready-to-drink shakes Add DI water to the main mixing vessel and heat to approximately 60°C + / - 2°C. Once the water reaches 60°C, add the sugar syrup (such as agave or date syrup) with slow stirring. Mix into solution. Weigh out the dry weights of the individual substances (vitamin / mineral blend and hydrolyzed protein) and combine in a separate vessel. Mix the dry ingredients thoroughly. Slowly add the combined dry ingredients directly to the main mixing vessel with gentle sweep agitation. Weigh out the EMO in a separate vessel. Heat the EMO to 60°C + / - 2°C. Slowly add the sunflower lecithin to the EMO and mix with moderate agitation (if necessary) until the sunflower lecithin is completely mixed into solution. Slowly add the EMO / sunflower lecithin mixture to the main mixing vessel. Increase the volume to 95% of the total fluid mass by adding distilled water and return the temperature to 70°C + / - 2°C. Slowly add flavors and colors to the main mixing vessel. Slowly add stabilizer (such as gum acacia) to the main mixing vessel. Mix solution for 20 minutes (to increase viscosity). Maintain temperature of solution at 70°C + / - 2°C. QS distilled water to bring solution to final volume. Pass material through pressure drop homogenizer(s) to produce stable emulsion. Pasteurize or sterilize material. Cool material to room temperature. Fill product into packaging.

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

[0193] Samples of the enzyme 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)-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 see AOCS Official Methods Cd 29a-13 or Cd 29c-13. Bound glycidol is the sum of all glycidyl derivatives that are cleaved by alkali-catalyzed alcoholysis. Bound glycidol content is reported in milligrams per kilogram (mg / kg). Bound 2-MCPD is the sum of all 2-MCPD derivatives that are cleaved by alkali-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 alkali-catalyzed alcoholysis. The content of bound 3-MCPD is reported in milligrams per kilogram (mg / kg). The method describes a procedure for the parallel determination of glycidol along with 2-MCPD and 3-MCPD present in bound or free form in fats and oils. The method is based on alkali-catalyzed ester cleavage, conversion of the liberated glycidol to monobromopropanediol (MBPD), and derivatization of the free diols (MCPD and MBPD) with phenylboronic acid (PBA). Although free MCPD and glycidol are present only in small to negligible amounts in fats and oils, significant content will increase proportionally with the determined amount of bound analyte. The 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 a total 2-MCPD (free and bound) and total 3-MCPD (free and bound) of less than 0.10 mg / kg, respectively, below the lower limit of quantification (0.10 mg / kg) of the assay for measuring MCPD. Thus, the sum of the total MCPD detected in the starting almond oil and enzyme-modified oil was less than 1.82 mg / kg and 0.10 mg / kg, respectively.

[0196] Thus, the present invention is well adapted to attain the ends and advantages mentioned, as well as those inherent therein. While many modifications may be made by those skilled in the art, such modifications are encompassed within the spirit of the invention as pointed out in part by the appended claims.

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

[0198] Fatty acids were analyzed as fatty acid methyl esters after derivatization and compared with standards. For derivatization, samples (500 μl) were 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 tridecanoic acid internal standard solution (10 mg / ml). The reaction tube was vortexed and incubated in a 60 °C heat block for 30 min. The reaction tube was removed from the heat block and cooled for 15 min. The reaction was then quenched by adding 1 ml of distilled water, followed by 1 ml of hexane. The reaction tube was vortexed for 60 s and the phases were allowed to separate for 3 min. The upper (hydrophobic) phase was transferred to a 1.5 ml tube containing approximately 50 mg of sodium sulfate (anhydrous). After vortexing for 60 s, 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. Samples were analyzed using an Agilent 7890A Gas Chromatograph with a Flame Ionization Detector and Agilent Openlab CDS Chemstation software. GC column: Omegawax 100 (15m x 0.1mm x 0.1um) column. Results were converted to weight percent by internal standard reference. [Table 9] TIFF0007654550000014.tif140152

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

[0200] Separate experiments were performed using almond oil and canola oil, yielding the data in Table 10, which show the same results for oleic acid, linoleic acid, and linolenic acid. [Table 10]

[0201] These results demonstrate that the manufacturing process of the present disclosure can preserve the fatty acid profile of the starting oil in the MAG oil, unlike conventional "distilled" oils, whose fatty acid profile differs significantly from the starting oil based on the functional use of the distilled oil.

[0202] These results also demonstrate that the processed oils of the present disclosure can be used to provide "complete nutrition" by providing linoleic and linolenic acids. Similar results are expected for high EPA and high DHA oils, such as fish and algae oils, to provide complete nutritional formulations.

[0203] Example 13: The EMO process preserves the essential fatty acids contained in the original oil Canola EMO was produced 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 and linolenic acids. Similar results were obtained with EMO from olive, sunflower and almond oils. Commercially available "monostearin" (Profood Products, Naperville, IL) contains little or no unsaturated fatty acids, and "Capmul GMO50" (Abitec Corporation, Janesville, WI) is primarily monosaturated, oleic, with little linoleic and virtually no linolenic or gondoic (C20:1) fatty acids.

[0204] Example 14: Beneficial compounds are preserved Vegetable oils contain trace amounts of many lipids, steroids, esters, and phenolic compounds that 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 standards (0.1-100 μg / mL) and 20 μL of the internal standard mixture were mixed and dried under nitrogen. To the dried residue, 200 μL of oxalyl chloride (2 M in dichloromethane) was added, and the mixture was incubated on a heat block at 65 °C for 5 min 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 min and subsequently dried under nitrogen to obtain the derivatized FA. The dried FA derivatives were dissolved in 1000 μL of ethanol and further diluted 10-fold with ethanol before LC-MS analysis. LC-MS analysis was in ionization mode: positive ionization (total fatty acids and lipidomics) and negative ionization (lipidomics). 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., monogalactodiacylglycerol), phosphatidylmethanol, steroids (e.g., sitosteryl esters), neutral lipids (e.g., campestrol esters), sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin. Coenzymes have also been found to be enhanced.

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

[0207] In a first embodiment, a food product comprises an oil and has a total caloric content of about 25 kcal to about 1,000 kcal, wherein about 5% to about 75% of the total caloric content is derived from the oil, the oil comprises less than 10% by weight of triacylglycerides (TAGs) based on the total weight of the oil, and the oil is substantially free of monochloropropanediol (MCPD).

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

[0209] In another aspect of the first embodiment, the oil comprises greater than 60 wt.% MAG, based on the total weight of the oil.

[0210] In another aspect of the first embodiment, the oil comprises greater than 70 wt.% MAG, based on the total weight of the oil.

[0211] In another aspect of the first embodiment, the oil comprises greater than 80 wt.% MAG, based on the total weight of the oil.

[0212] In another aspect of the first embodiment, the oil comprises greater than 90 wt.% MAG, based on the total weight of the oil.

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

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

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

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

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

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

[0219] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product further comprises a carbohydrate source, wherein the carbohydrate source comprises a simple sugar.

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

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

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

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

[0224] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product comprises a carbohydrate source and further comprises a protein source, the protein source comprises hydrolyzed or partially hydrolyzed protein, and the hydrolyzed protein is selected from hydrolyzed pulse protein and a whey-based hydrolysate.

[0225] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product further comprises a protein source.

[0226] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product further comprises a protein source, wherein about 10% to about 50% of calories are derived from the protein source.

[0227] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product further comprises a protein source, wherein the protein source comprises hydrolyzed or partially hydrolyzed protein.

[0228] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the food product further comprises a protein source, the protein source comprising hydrolyzed or partially hydrolyzed protein, and the hydrolyzed protein is selected from hydrolyzed pulse protein and a whey-based hydrolysate product.

[0229] In another aspect of the first embodiment, or any of the preceding 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 any of the preceding aspects of the first embodiment, the oil is a processed oil derived from an oil source, and the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil.

[0231] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the oil is a processed oil derived from an oil source, and the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not 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 any of the preceding aspects of the first embodiment, the oil is a processed oil derived from an oil source, and the processed oil includes non-oil components derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is a tocopherol.

[0233] In another aspect of the first embodiment, or any of the preceding aspects of the first embodiment, the oil is a processed oil derived from an oil source, and the processed oil includes non-oil components derived from and naturally occurring in the oil source, such that the non-oil components are not added to the processed oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is a 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 a second embodiment, a food product comprises a processed oil, a carbohydrate source, and a protein source, and has a total weight of about 25 grams to about 500 grams with a caloric density of about 1 kcal to about 5 kcal per gram, the processed oil comprises about 10% to about 50% of the total caloric content, the processed oil has a MAG content of 40% or more by weight based on the total weight of the processed oil, and a TAG content of 10% or less by weight 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 a third embodiment, the product comprises a processed oil derived from an oil source, the processed oil comprising a MAG content of 40 wt% or greater of the total weight of the processed oil, the processed oil is free of TAG or comprises a TAG content of 10 wt% or less of the total weight of the processed oil, the processed oil comprises non-oil components derived from and naturally present in the oil source, such that no non-oil components are added to the processed oil, the oil source comprises from about 1.00 mg / kg to about 12.00 mg / kg of MCPD, and the processed oil comprises less than 0.100 mg / kg of MCPD.

[0236] In one aspect of the third embodiment, the oil source is 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 any of the preceding aspects of the third embodiment, the non-oily ingredient is selected from the group consisting of antioxidants, vitamins, and mixtures thereof.

[0240] In another aspect of the third embodiment, or any of the preceding aspects of the third embodiment, the non-oily 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 any of the preceding 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 a 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 any of the preceding aspects of the third embodiment, the process oil comprises a MAG content of about 50% to about 95% by weight, based on the total weight of the process oil.

[0243] In another aspect of the third embodiment, or any of the preceding aspects of the third embodiment, the processing oil comprises a MAG content of about 50 wt.% to about 95 wt.%, based on the total weight of the processing oil, and the processing oil comprises 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 any of the preceding aspects of the third embodiment, the processing oil comprises 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 an oil enriched in monoacylglycerol includes combining a starting oil comprising triacylglycerol (TAG) and about 1.00 mg / kg to about 12.00 mg / kg MCPD, where the TAG is in an amount greater than 50% by weight based on the total weight of the starting oil, with a buffer and a first enzyme capable of hydrolyzing the TAG to free fatty acids (FFAs) 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 of time to produce a first lipid reaction product comprising an aqueous phase and FFAs; and 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 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 to separate a 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 source.

[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 a 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 is a sodium citrate solution.

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

[0253] In another aspect of the fourth embodiment, the first period of time 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 performed at a temperature of about 30°C to about 35°C.

[0255] In another aspect of the fourth embodiment, the steps of mixing a starting oil comprising triacylglycerol (TAG), a buffer, and a first enzyme capable of hydrolyzing the TAG to free fatty acids (FFAs) and reacting the reaction mixture under conditions sufficient for the first enzyme to hydrolyze the TAG to FFAs are performed under a nitrogen atmosphere.

[0256] In another aspect of the fourth embodiment, the second enzyme is a 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 of time is sufficient to result in a concentration of MAG in the lipid oil phase of about 60% to 95%.

[0259] In another aspect of the fourth embodiment, the second period of time 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 of time to produce a lipid oil phase and a glycerol phase is performed at a temperature of about 17°C to 23°C.

[0261] In another aspect of the fourth embodiment, or any of the preceding aspects of the fourth embodiment, the method further includes drying the second lipid reaction product by applying a vacuum for a third period of time 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 any of the preceding aspects of the fourth embodiment, the method further comprises drying the second lipid reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of water from the second lipid reaction product, wherein the step of drying the second lipid reaction product is performed at a temperature between 20° C. and 30° C.

[0263] In another aspect of the fourth embodiment, or any of the preceding aspects of the fourth embodiment, the method further includes drying the second lipid reaction product by applying a vacuum for a third period of time sufficient to remove at least a portion of the water from the second lipid reaction product, the drying step being applied throughout the second period of time.

[0264] In another aspect of the fourth embodiment, or any of the preceding 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 any of the preceding aspects of the fourth embodiment, the step of inactivating the second enzyme is performed by heating the second lipid reaction product, wherein the heating is performed at a temperature of at least 70° C. for at least 1 hour.

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

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

[0268] In another aspect of the fourth embodiment, or any of the preceding aspects of the fourth embodiment, the method further comprises re-establishing a nitrogen atmosphere over the first lipid reaction product prior to combining the first lipid reaction product with food grade glycerol and a second enzyme capable of esterifying FFAs and glycerol.

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

[0270] In another aspect of the fourth embodiment, or any of the preceding aspects of the fourth embodiment, the lipid oil phase comprises MAG in an amount of about 40% by weight 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 comprises TAG in an amount of about 0.1% by weight to about 10% by weight, based on the total weight of the lipid oil phase.

[0271] In a fifth embodiment, the processed oil has a total fatty acid content comprising monoglyceride of oleic acid (MOG), the MOG comprising from about 5% to about 75% by weight of the total fatty acid content of the processed oil.

[0272] In an aspect of the fifth embodiment, the processed oil comprises less than 10 wt. % triacylglycerides (TAGs) based on the total weight of the processed oil.

[0273] In another aspect of the fifth embodiment, the process oil comprises greater than 50 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

[0274] In another aspect of the fifth embodiment, the process oil comprises greater than 60% by weight monoacylglycerides (MAG), based on the total weight of the process oil.

[0275] In another aspect of the fifth embodiment, the process oil comprises greater than 70% by weight monoacylglycerides (MAG), based on the total weight of the process oil.

[0276] In another aspect of the fifth embodiment, the process oil comprises greater than 80% by weight monoacylglycerides (MAG), based on the total weight of the process oil.

[0277] In another aspect of the fifth embodiment, the process oil comprises greater than 90% by weight monoacylglycerides (MAG), based on the total weight of the process oil.

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

[0279] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil is a processed oil derived from an oil source, and the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil.

[0280] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil is a processed oil derived from an oil source, and the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof.

[0281] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil is a processed oil derived from an oil source, the processed oil includes non-oil components derived from and naturally occurring in the oil source, such that the non-oil components are not added to the processed oil, and the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is a tocopherol.

[0282] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil is derived from an oil source, the processed oil includes non-oil components derived from and naturally occurring in the oil source, such that the non-oil components are not added to the processed oil, the non-oil components are selected from antioxidants, vitamins, and mixtures thereof, and the antioxidant is a tocopherol, the tocopherol being 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 any of the preceding aspects of the fifth embodiment, the processing oil is substantially free of monochloropropanediol (MCPD).

[0284] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processing oil has less than 0.10 mg / kg monochloropropanediol (MCPD).

[0285] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the oil source is from a source selected from a plant, an animal, an algae, or a fish.

[0286] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the oil source is from a plant.

[0287] In another aspect of the fifth embodiment or any of the preceding aspects of the fifth embodiment, the oil source is selected from 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.

[0288] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processing oil comprises a MAG content of about 50% to about 95% by weight, based on the total weight of the processing oil.

[0289] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processing oil comprises a TAG content of about 5% to about 0.5% by weight, based on the total weight of the processing oil.

[0290] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the MOG in the processed oil comprises at least 50% 1-oleyl monoglyceride by weight of the total amount of MOG.

[0291] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the MOG in the processed oil comprises at least 60% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0292] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the MOG in the processed oil comprises at least 70% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0293] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the MOG in the processed oil comprises at least 80% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0294] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in the processed oil in an amount from about 1.5% to about 90% by weight of the total fatty acid content of the processed oil.

[0295] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in the processed oil in an amount from about 10% by weight to about 90% by weight of the total fatty acid content of the processed oil.

[0296] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in the processed oil in an amount from about 20% by weight to about 90% by weight of the total fatty acid content of the processed oil.

[0297] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in the processed oil in an amount from about 10% to about 25% by weight of the total fatty acid content of the processed oil.

[0298] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in the processed oil in an amount from about 0.01% to about 2% by weight of the total fatty acid content of the processed oil.

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

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

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

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

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

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

[0305] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil has substantially the same fatty acid profile as the fatty acid profile of the pre-processed oil from which the processed oil is produced.

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

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

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

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

[0310] In another aspect of the fifth embodiment, or any of the preceding aspects of the fifth embodiment, the processed oil comprises oleic acid in the form of oleic acid monoglyceride in about the same amount as the amount of oleic acid in the pre-processed oil from which the processed oil is produced.

[0311] In a sixth embodiment, the processed oil has a fatty acid profile comprising oleic acid, linoleic acid, and linolenic acid, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 10% of the amount of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil was generated, and the processed oil comprises greater than 50% by weight monoacylglycerides (MAGs) based on the total weight of the processed oil.

[0312] In a seventh embodiment, the processed oil has a fatty acid profile comprising oleic acid, linoleic acid, and linolenic acid, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 1%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil was generated, and the processed oil comprises greater than 50% by weight monoacylglycerides (MAGs) based on the total weight of the processed oil.

[0313] In an eighth embodiment, the processed oil comprises oleic acid and linoleic acid, the ratio of oleic acid to linoleic acid in the processed oil is from about 0.01 to about 5, and the processed oil comprises greater than 50% by weight of monoacylglycerides (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 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 about 3 to about 4.

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

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

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

[0319] In a ninth embodiment, the processed oil comprises oleic acid and linoleic acid, the ratio of oleic acid to linoleic acid in the processed oil is from about 1 to about 100, and the processed oil comprises greater than 50 wt.% monoacylglycerides (MAG) based on the total weight of the processed oil.

[0320] In a tenth embodiment, the processed oil comprises oleic acid and linoleic acid, the ratio of oleic acid to linoleic acid in the processed oil is from about 10 to about 100, and the processed oil comprises greater than 50 wt.% monoacylglycerides (MAG) based on the total weight of the processed oil.

[0321] In an eleventh embodiment, the processed oil comprises oleic acid and linoleic acid, the ratio of oleic acid to linoleic acid in the processed oil is from about 10 to about 30, and the processed oil comprises greater than 50 wt.% monoacylglycerides (MAG) based on the total weight of the processed oil.

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

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

[0324] In one aspect of the ninth, tenth, or eleventh embodiments, the processed oil further comprises linoleic acid, and the ratio of oleic acid to linoleic acid in the processed oil is about 3 to about 4.

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

[0326] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding 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 aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding 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 aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding 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 aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding 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 80% by weight of the total amount of MOG is 1-oleyl monoglyceride.

[0330] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises less than 10 wt. % triacylglycerides (TAGs) based on the total weight of the processed oil.

[0331] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises greater than 50 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0332] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises greater than 60 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0333] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises greater than 70 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0334] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises greater than 80 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0335] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil comprises greater than 90 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

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

[0337] In one aspect of the foregoing embodiments, the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil.

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

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

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

[0341] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processing oil is substantially free of monochloropropanediol (MCPD).

[0342] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processing oil has less than 0.10 mg / kg monochloropropanediol (MCPD).

[0343] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the oil source is derived from a source selected from a plant, an animal, an algae, or a fish.

[0344] In one aspect of the foregoing, the oil source is from a plant.

[0345] In one aspect of the foregoing embodiment, the oil source is selected from 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.

[0346] In an aspect of the eighth, ninth, tenth, or eleventh embodiment, and any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processing oil comprises a MAG content of about 50% to about 95% by weight, based on the total weight of the processing oil.

[0347] In an aspect of the eighth, ninth, tenth, or eleventh embodiment, and any of the foregoing aspects of the eighth, ninth, tenth, or eleventh embodiment, the processing oil comprises a TAG content of about 5 wt.% to about 0.5 wt.%, based on the total weight of the processing oil.

[0348] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiment, the processed oil has a fatty acid profile substantially the same as the fatty acid profile of the pre-processed oil from which the processed oil is produced.

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

[0350] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiments, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 10%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is generated.

[0351] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiments, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 1%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is generated.

[0352] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiments, the processed oil comprises three times the amount of MAG as compared to the amount of TAG in the pre-processing oil from which the processed oil is generated.

[0353] In aspects of the eighth, ninth, tenth, or eleventh embodiment, and any of the preceding aspects of the eighth, ninth, tenth, or eleventh embodiments, the processed oil comprises oleic acid in the form of oleic acid monoglyceride in about the same amount as the amount of oleic acid in the pre-processed oil from which the processed oil is produced.

[0354] In a twelfth embodiment, the processed oil has a total fatty acid content comprising oleic acid and linoleic acid, the linoleic acid being present in an amount of about 10% to about 90% by weight of the total fatty acid content of the processed oil, and the processed oil comprises greater than 50% by weight monoacylglycerides (MAGs) based on the total weight of the processed oil.

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

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

[0357] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the processed oil further comprises linoleic acid, the linoleic acid being present in an amount of about 0.01% to about 2% by weight of the total fatty acid content of the processed oil.

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

[0359] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is from about 1 to about 4.

[0360] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is about 3 to about 4.

[0361] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is from about 1 to about 100.

[0362] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is from about 10 to about 100.

[0363] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the ratio of oleic acid to linoleic acid in the processed oil is about 10 to about 30.

[0364] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, at least a portion of the oleic acid is present in the form of monooleic acid glyceride (MOG).

[0365] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the MOG in the processed oil comprises at least 50% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0366] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the MOG in the processed oil comprises at least 60% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0367] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the MOG in the processed oil comprises at least 70% by weight 1-oleyl monoglyceride of the total amount of MOG.

[0368] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the MOG in the processed oil comprises at least 80% by weight of 1-oleyl monoglyceride of the total amount of MOG.

[0369] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises less than 10 wt. % triacylglycerides (TAGs), based on the total weight of the process oil.

[0370] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises greater than 50 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

[0371] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises greater than 60 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

[0372] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises greater than 70 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

[0373] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises greater than 80 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

[0374] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises greater than 90 wt. % monoacylglycerides (MAG), based on the total weight of the process oil.

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

[0376] In one aspect of the foregoing embodiments, the processed oil includes non-oil components that are derived from and naturally present in the oil source, such that the non-oil components are not added to the processed oil.

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

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

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

[0380] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil is substantially free of monochloropropanediol (MCPD).

[0381] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the processing oil has less than 0.10 mg / kg monochloropropanediol (MCPD).

[0382] In an aspect of the twelfth embodiment, or any of the above aspects of the twelfth embodiment, the oil source is from a source selected from a plant, an animal, an algae, or a fish.

[0383] In one aspect of the foregoing embodiments, the oil source is from a plant.

[0384] In one aspect of the foregoing embodiment, the oil source is selected from 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.

[0385] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises a MAG content of about 50% to about 95% by weight, based on the total weight of the process oil.

[0386] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the process oil comprises a TAG content of about 5% to about 0.5% by weight, based on the total weight of the process oil.

[0387] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the processed oil has substantially the same fatty acid profile as the fatty acid profile of the pre-processed oil from which the processed oil is produced.

[0388] In one aspect of the foregoing, the fatty acid profile comprises oleic acid, linoleic acid, and linolenic acid.

[0389] In one aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 10%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is generated.

[0390] In one aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 1%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil is generated.

[0391] In an aspect of the twelfth embodiment, or any of the preceding aspects of the twelfth embodiment, the processed oil comprises about the same amount of MAG as compared to the amount of TAG in the pre-processing oil from which the processed oil was produced.

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

[0393] In a thirteenth embodiment, the processed oil has a fatty acid profile comprising oleic acid, linoleic acid, and linolenic acid, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 10% of the amount of oleic acid, linoleic acid, and linolenic acid, respectively, in the pre-processed oil from which the processed oil was generated, and the processed oil comprises greater than 50% by weight monoacylglycerides (MAG), based on the total weight of the processed oil.

[0394] In a fourteenth embodiment, the processed oil has a fatty acid profile comprising oleic acid, linoleic acid, and linolenic acid, the amount of oleic acid, linoleic acid, and linolenic acid in the processed oil is within about 1%, respectively, of the amount of oleic acid, linoleic acid, and linolenic acid in the pre-processed oil from which the processed oil was generated, and the processed oil comprises greater than 50% by weight monoacylglycerides (MAGs) based on the total weight of the processed oil.

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

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

[0397] In a seventeenth embodiment, a method of promoting glucose homeostasis in a subject in need thereof comprises administering to the subject a composition comprising a processed oil comprising oleic acid monoglyceride (MOG), wherein at least 50% by weight of the MOG is 1-oleyl monoglyceride.

[0398] In an eighteenth embodiment, a method of treating diabetes in a subject in need thereof comprises administering to the subject a composition comprising a processed oil comprising oleic acid monoglyceride (MOG), wherein at least 50% by weight of the MOG is 1-oleyl monoglyceride.

[0399] In an aspect of the seventeenth or eighteenth embodiment, at least 60% by weight of the MOG is 1-oleyl monoglyceride.

[0400] In another aspect of the seventeenth or eighteenth embodiment, at least 70% by weight of the MOG is 1-oleyl monoglyceride.

[0401] In another aspect of the seventeenth or eighteenth embodiment, at least 80% by weight of the MOG is 1-oleyl monoglyceride.

[0402] In an aspect of the fifteenth, sixteenth, seventeenth, or eighteenth embodiment, or any of the aforementioned aspects of the seventeenth or eighteenth embodiment, the processing oil is a processing oil according to any one of the fifth to fourteenth embodiments, and any of the aforementioned aspects thereof.

[0403] In the fifteenth, sixteenth, seventeenth, or eighteenth embodiment, or any of the preceding aspects of the fifteenth, sixteenth, seventeenth, or eighteenth embodiment, the composition is a food product comprising the processed oil of the food product of any of the first, second, or third embodiments, and any of the preceding aspects thereof.

[0404] In an aspect of the fifteenth or seventeenth embodiment, or any of the preceding aspects of the fifteenth or seventeenth embodiment, the subject suffers from a condition that affects glucose homeostasis.

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

[0406] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 10% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[0407] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 20% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[0408] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 30% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[0409] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 40% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[0410] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 50% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[0411] In an aspect of the fifth, sixth, or seventh embodiment, or any of the preceding aspects of the fifth, sixth, or seventh embodiment, the MOG contributes from about 60% to about 75% by weight of the total fatty acid content of the processed oil.

[0412] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from 5% to about 75% by weight of the fatty acid content of the processed oil.

[0413] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from about 10% to about 75% by weight of the total fatty acid content of the processed oil.

[0414] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from about 20% to about 75% by weight of the total fatty acid content of the processed oil.

[0415] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from about 30% to about 75% by weight of the total fatty acid content of the processed oil.

[0416] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from about 40% to about 75% by weight of the total fatty acid content of the processed oil.

[0417] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing from about 50% to about 75% by weight of the total fatty acid content of the processed oil.

[0418] In an aspect of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, or any of the foregoing aspects of the eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiment, the processed oil comprises monooleic acid (MOG) in an amount contributing about 60% to about 75% by weight of the total fatty acid content of the processed oil.

[0419] In a nineteenth embodiment, the processed oil has a fatty acid profile, wherein the fatty acid profile of the processed oil is substantially the same as the pre-processed oil from which the processed oil is generated, and wherein the processed oil comprises greater than 50 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0420] In a twentieth embodiment, a food product comprises the processed oil of any of the fifth, sixth, seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiments, or any of the aforementioned aspects of the fifth, sixth, seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth, or fourteenth embodiments.

[0421] In a twenty-first embodiment, the processed oil has a total fatty acid content comprising greater than 50 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0422] In a twenty-second embodiment, the processed oil has a total fatty acid content comprising greater than 60 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0423] In a twenty-third embodiment, the processed oil has a total fatty acid content comprising greater than 70 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0424] In a twenty-fourth embodiment, the processed oil has a total fatty acid content comprising greater than 80 wt.% monoacylglycerides (MAG), based on the total weight of the processed oil.

[0425] In a twenty-fifth embodiment, the processed oil has a total fatty acid content comprising greater than 90% by weight monoacylglycerides (MAG), based on the total weight of the processed oil.

[0426] In an aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 5% to about 75% by weight of the total fatty acid content of the processed oil.

[0427] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 10% to about 75% by weight of the total fatty acid content of the processed oil.

[0428] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 20% to about 75% by weight of the total fatty acid content of the processed oil.

[0429] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 30% to about 75% by weight of the total fatty acid content of the processed oil.

[0430] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 40% to about 75% by weight of the total fatty acid content of the processed oil.

[0431] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 50% to about 75% by weight of the total fatty acid content of the processed oil.

[0432] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid in an amount from about 60% to about 75% by weight of the total fatty acid content of the processed oil.

[0433] In an aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, or any of the preceding aspects of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises linoleic acid in an amount from about 1.5% to about 90% by weight of the total fatty acid content of the processed oil.

[0434] In an aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, or any of the preceding aspects of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises linoleic acid in an amount from about 10% to about 25% by weight of the total fatty acid content of the processed oil.

[0435] In an aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, or any of the preceding aspects of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises linoleic acid in an amount from about 0.1% to about 2% by weight of the total fatty acid content of the processed oil.

[0436] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 0.01-5.

[0437] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 1-4.

[0438] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 3-4.

[0439] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 1-100.

[0440] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 10-100.

[0441] In another aspect of the twenty-first, twenty-second, twenty-third, twenty-fourth, or twenty-fifth embodiment, the processed oil further comprises oleic acid and linoleic acid, wherein the ratio of oleic acid to linoleic acid is about 10-30.

[0442] Further embodiments of the present invention will be described below. [1] A processed oil comprising monoacylglycerol (MAG), diacylglycerol (DAG), and free fatty acids (FFA), wherein MAG constitutes about 30% by weight to about 90% by weight of the total weight of the processed oil, DAG constitutes about 10% by weight to about 30% by weight of the total weight of the processed oil, and FFA constitutes about 5% by weight to about 60% by weight of the total weight of the processed oil, further comprising non-oil components naturally present in the processed oil, and the processed oil is substantially free of monochloropropanediol (MCPD). [2] The processing oil according to [1], further comprising triacylglycerol (TAG), the TAG constituting 5% by weight or less of the total weight of the processing oil. [3] The processing oil according to [1] or [2], wherein the non-oil components include an antioxidant. [4] The processing oil according to [3], wherein the antioxidant is tocopherol. [5] The processed oil according to [1] or [2], wherein the non-oil components include vitamins. [6] The processing oil according to [1] or [2], wherein the non-oil components include one or more of ceramide phosphate, monogalactosyl diacylglycerol, phosphatidylmethanol, sitosteryl esters, campestrol esters, sphingolipids, phosphatidylglycerol, wax esters, and sphingomyelin. [7] The processed oil according to any one of [1] to [6], wherein the processed oil is derived from an oil source selected from the group consisting of safflower oil, grape oil, milk thistle (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] The processed oil according to any one of [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 [1] to [6], wherein the processing oil is derived from algae or fish.

[10] The processing oil according to any one of [1] to [9], wherein the processing oil has a fatty acid content including oleic acid, linoleic acid, and linolenic acid.

[11] The processed oil according to

[10] , wherein the amount of the oleic acid is 10% by weight to about 75% by weight of the total fatty acid content of the processed oil.

[12] The processing oil according to

[11] , wherein about 50% to about 99% of the oleic acid content is esterified at the sn-1 position.

[13] The processed oil according to

[10] , wherein the amount of linoleic acid is 1.5% by weight to about 90% by weight of the total fatty acid content of the processed oil.

[14] The processed oil according to

[10] , wherein the amount of linolenic acid is 0.01% by weight to about 2% by weight of the total fatty acid content of the processed oil.

[15] A processing oil for the following process: mixing a starting oil with a buffer and a first enzyme to generate a first reaction mixture, wherein the starting oil comprises triacylglycerol (TAG) and monochloropropanediol (MCPD), the TAG being in an amount greater than 50% by weight 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% by weight 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 TAG for a first period of time to produce a first lipid reaction product comprising an aqueous phase and 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 the 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] The processing oil of

[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] The processing oil of

[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 the one or more naturally occurring non-oil components are maintained in the processing oil.

[18] 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] The food product described in

[18] , wherein the processed oil has a monoacylglycerol (MAG) content of 30% by weight or more based on the total weight of the processed oil.

[20] The food product of

[18] or

[19] , wherein the processed oil has a diacylglycerol (DAG) content of about 10% by weight to about 30% by weight based on the total weight of the processed oil.

[21] The food product described in any one of

[18] to

[20] , wherein the processed oil has a free fatty acid (FFA) content of about 5% by weight to about 60% by weight based on the total weight of the processed oil.

[22] The food according to any one of

[18] to

[21] , wherein the processed oil contains non-oil components naturally occurring in the processed oil, and the non-oil components contain one or more of ceramide phosphate, monogalactosyl diacylglycerol, phosphatidylmethanol, cytosteryl ester, camptosterol ester, sphingolipid, phosphatidylglycerol, wax ester, and sphingomyelin.

[23] The food according to any one of

[18] to

[22] , wherein the amount of the oleic acid is 10% by weight to approximately 75% by weight of the total fatty acid content of the processed oil.

[24] The food according to any one of

[18] to

[23] , wherein approximately 50% to approximately 99% of the oleic acid content is esterified at the sn-1 position.

[25] The food according to any one of

[18] to

[24] , wherein the amount of linoleic acid is 1.5% by weight to approximately 90% by weight of the total fatty acid content of the processed oil.

[26] The food according to any one of

[18] to

[25] , wherein the amount of linolenic acid is 0.01% by weight to approximately 2% by weight of the total fatty acid content of the processed oil. The foregoing description of specific embodiments of the present disclosure has been presented for purposes of illustration and description. The exemplary embodiments have been chosen and described in order to best explain the principles of the present disclosure and its practical application, thereby enabling those skilled in the art to best utilize the subject matter, and various embodiments with various modifications are suitable for the particular use contemplated. Different features and disclosures of various embodiments within the present disclosure can be combined within the scope of the present disclosure.

Claims

1. A processed oil comprising monoacylglycerols (MAG), diacylglycerols (DAG), free fatty acids (FFA), and triacylglycerols (TAG), MAG constitutes 30% to 90% by weight of the total weight of the processing oil; DAG is 5% by weight or more of the total weight of the processing oil, FFAs constitute 5% to 60% by weight of the total weight of the processing oil; TAG constitutes 5% or less by weight of the total weight of the processing oil; the processing oil further comprises non-oil components naturally present in the processing oil, wherein the non-oil components comprise an antioxidant that is a tocopherol; The processing oil is substantially free of monochloropropanediol (MCPD), 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; The processing oil.

2. 10. The processing oil of claim 1, wherein the processing oil has a fatty acid content comprising oleic acid, linoleic acid, and linolenic acid.

3. 3. The processed oil of claim 2, wherein the amount of oleic acid is from 10% to 75% by weight of the total fatty acid content of the processed oil.

4. 4. The processing oil of claim 3, wherein 50% to 99% of the oleic acid content is esterified at the sn-1 position.

5. 3. The processed oil of claim 2, wherein the amount of linoleic acid is from 1.5% to 90% by weight of the total fatty acid content of the processed oil.

6. 3. The processed oil of claim 2, wherein the amount of linoleic acid is from 0.01% to 2% by weight of the total fatty acid content of the processed oil.

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