Fat / oil composition and method for producing same

Abstract

Provided is a method for efficiently producing a fat / oil composition containing a TAG having a high concentration of a target highly unsaturated fatty acid as a constituent fatty acid, a method for producing a TAG at a low temperature in a short time, and a composition in which the content of harmful oligomers is reduced. Also provided is a method for producing a fat / oil composition which contains acylglycerols and in which the acylglycerols include a triacylglycerol, the method comprising: reacting glycerol or a C1-6 fatty acid glycerol ester and a fatty acid composition containing a fatty acid or a C1-6 alcohol ester thereof in the presence of a C1-6 alcohol and a catalyst to obtain a fat / oil composition containing a triacylglycerol generated by the reaction.

Description

Oil and fat composition and method for producing the same

[0001] The present disclosure relates to an oil or fat composition containing an acylglycerol, wherein the acylglycerol comprises a triacylglycerol, and a method for producing the same.

[0002] ω-3 highly unsaturated fatty acids are found in large amounts in fish oils such as those from mackerel and sardines. ω-3 highly unsaturated fatty acids have been known as useful substances for lowering cholesterol and preventing thrombosis, and are widely used as raw materials in health foods and pharmaceuticals. ω-3 highly unsaturated fatty acids are known to be ingested as their ethyl esters (hereinafter, fatty acid ethyl esters are also referred to as EE), but they are also known to be ingested as triacylglycerols (hereinafter, also referred to as TAG) (Non-Patent Document 1). A common method for concentrating ω-3 highly unsaturated fatty acids contained in TAG involves partial hydrolysis of TAG using an enzyme with substrate specificity for the fatty acid species, but this method has limitations in terms of the degree of concentration. Alternatively, an esterification reaction using glycerol or a lower fatty acid glycerol ester with a free fatty acid or a fatty acid lower alcohol ester is also known. By carrying out this method using free fatty acids or fatty acid lower alcohol esters containing a high concentration of ω-3 highly unsaturated fatty acids, it is possible to obtain TAGs containing a high concentration of ω-3 highly unsaturated fatty acids as constituent fatty acids. In other words, by preparing TAGs containing fatty acids derived from free fatty acids or fatty acid lower alcohol esters that are enriched with target fatty acid species, it is possible to prepare TAGs having a fatty acid composition that cannot be achieved with natural fats and oils or other processed fats and oils.

[0003] It is widely known that enzyme-catalyzed reactions or alkali-catalyzed reactions are used to prepare the above-mentioned TAGs. Among these, enzyme-catalyzed reactions have the drawback of high reaction costs due to the high cost of the enzymes and the limited number of times they can be reused. On the other hand, alkali-catalyzed reactions have the drawback of requiring higher reaction temperatures, which can lead to deterioration in quality, such as coloration and an increase in the peroxide value, although the catalysts are less expensive than enzymes (Patent Documents 1 to 3).

[0004] One quality criterion for oils and fats is the content of impurities defined as oligomers. For example, the European Pharmacopoeia specifies a maximum oligomer content of 1.5% for fish oil containing ω-3 highly unsaturated fatty acids (Non-Patent Document 2). The toxicity of oligomers became apparent in research into the nutritional value of thermally polymerized oils. Kaneda et al. demonstrated that thermally polymerized oils were toxic in animal tests (Non-Patent Document 3). Searches for the causative agent identified oligomers (glyceride dimers) as the toxic substance (Non-Patent Document 4). It is known that the amount of oligomers produced increases depending on the thermal history. In TAG oils, which are produced by esterification using glycerol or lower fatty acid glycerol esters with free fatty acids or lower fatty acid alcohol esters, existing methods are thought to produce large amounts of oligomers due to the high heating temperature or long heating time during the esterification reaction. Furthermore, a previous report confirmed that products produced using enzyme catalysts also contained 2.9% oligomers (Patent Document 4).

[0005] Chinese Patent No. 103242969 JP 1-93558 JP 7-42787 JP 5-331105

[0006] Wojenski, Carol M., et al. Biochimica et Biophysica Acta (BBA)-Lipids and Lipid Metabolism 1081.1 (1991): 33-38.EUROPEAN PHARMACOPOEIA 8.0 Oil Chemistry. 17.69-72. (1968) Oil Chemistry. 21.13-19. (1972)

[0007] In response to the above-mentioned problems, there is still a need for a method for efficiently producing an oil or fat composition containing TAG containing a high concentration of a target highly unsaturated fatty acid as a constituent fatty acid. There is also a need for a composition in which the content of harmful oligomers is reduced in the production of the oil or fat composition. Furthermore, there is a need for a method for synthesizing TAG at a low temperature in a short time.

[0008] The inventors C １－６Glycerol or C in the presence of an alcohol and a catalyst １－６ Fatty acid glycerol ester and a fatty acid or its C １－６ The inventors have discovered that the above problems can be solved by subjecting a fatty acid composition containing an alcohol ester to a reaction, and that a TAG oil with a low oligomer content can be obtained through a reaction at a low temperature and for a short time.

[0009] The present disclosure provides the following oil and fat compositions and methods for producing the same.

[0010] [1-1] A method for producing an oil or fat composition containing an acylglycerol, wherein the acylglycerol contains a triacylglycerol, comprising: １－６ Glycerol or C in the presence of an alcohol and a catalyst １－６ Fatty acid glycerol ester and a fatty acid or its C １－６ a fatty acid composition containing an alcohol ester being subjected to a reaction, and an oil or fat composition being produced by the reaction.

[0011] [1-2] During the reaction, the C １－６ The method according to [1-1], which comprises removing alcohol.

[0012] [1-3] The glycerol or C １－６ a fatty acid glycerol ester, the catalyst, and the C １－６ and an alcohol to obtain a catalyst mixture; and mixing the catalyst mixture and the fatty acid composition, and subjecting the resulting reaction mixture to the reaction. The method according to [1-1] or [1-2], comprising:

[0013] [1-4] The method according to [1-3], wherein mixing the catalyst mixture and the fatty acid composition comprises adding the fatty acid composition to the catalyst mixture.

[0014] [1-5] The method according to [1-4], wherein the catalyst mixture is mixed at 30°C to 50°C, and then the fatty acid composition is added.

[0015] [1-6] The method according to any one of [1-1] to [1-5], wherein the catalyst is an alkaline catalyst.

[0016] [1-7] The method according to any one of [1-1] to [1-6], wherein the reaction is carried out at 40°C to 160°C.

[0017] [1-8] The method according to any one of [1-1] to [1-7], wherein the reaction is carried out at 3000 Pa or less.

[0018] [1-9] The fatty acid composition and the C １－６ The method according to any one of [1-1] to [1-8], wherein the weight ratio of alcohol is 2:1 to 1:10.

[0019] [1-10] The glycerol or C １－６ The C for fatty acid glycerol ester １－６ The method according to any one of [1-1] to [1-9], wherein the molar ratio of alcohol is 1:10 or more and 1:100 or less.

[0020] [1-11] The method according to any one of [1-1] to [1-10], wherein the catalyst is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium alcoholate, or potassium alcoholate.

[0021] [1-12] The method according to any one of [1-1] to [1-11], wherein the reaction is carried out at 1000 Pa or less.

[0022] [1-13] The method according to any one of [1-1] to [1-12], wherein the fatty acid composition is derived from marine oil or microbial oil.

[0023] [1-14] The fatty acid composition is PUFA or its C １－６ The method according to any one of [1-1] to [1-13], wherein the alcohol ester is contained in an amount of 25% by weight or more.

[0024] [1-15] The above C １－６ The method according to any one of [1-1] to [1-14], wherein the alcohol is ethanol.

[0025] [1-16] The method according to any one of [1-1] to [1-15], wherein the fatty acid composition contains a total of 25% by weight or more of ethyl ester of EPA and ethyl ester of DHA.

[0026] [1-17] The method for producing an oil or fat composition according to any one of [1-1] to [1-16], wherein, among the fatty acids that are constituent fatty acids of acylglycerols in the oil or fat composition, three or more fatty acids are present in a weight ratio of 5 wt % or more relative to all constituent fatty acids, at least one of the fatty acids present in a weight ratio of 5 wt % or more is a PUFA, for all of the fatty acids present in a weight ratio of 5 wt % or more, the ratio of the weight ratio in all constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil or fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

[0027] [1-18] The method according to [1-17], wherein the PUFA in the oil and fat composition contains ω3 highly unsaturated fatty acids.

[0028] [1-19] The method according to [1-17] or [1-18], wherein the PUFA in the oil or fat composition contains EPA or DHA.

[0029] [1-20] The production method according to any one of [1-17] to [1-19], wherein, among the constituent fatty acids of an acylglycerol, all fatty acids present in a weight ratio of 1% by weight or more relative to the total constituent fatty acids have a weight ratio of 7:10 or more to 13:10 or less at the sn2 position.

[0030] [1-21] The manufacturing method according to any one of [1-17] to [1-20], wherein the content of oligomers in the oil and fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area% or less.

[0031] [1-22] The method according to any one of [1-17] to [1-21], wherein the oil or fat composition contains triacylglycerol in an amount of 50% by weight or more.

[0032] [1-23] The method according to any one of [1-17] to [1-22], wherein the oil or fat composition further contains 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

[0033] [1-24] The method according to [1-23], wherein the oil or fat composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

[0034] [1-25] The method according to any one of [1-17] to [1-24], wherein the constituent fatty acids contain PUFAs in a proportion of 25% by weight or more.

[0035] [1-26] The method according to any one of [1-17] to [1-25], wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

[0036] [2-1] A method for producing an oil or fat composition containing acylglycerol, wherein the acylglycerol includes triacylglycerol, comprising: １－６ A production method comprising: reacting glycerol with a fatty acid composition containing an ethyl ester of a fatty acid in the presence of an alcohol and a catalyst, and obtaining an oil or fat composition produced by the reaction.

[0037] [2-2] During the reaction, the C １－６ The method according to [2-1], which comprises removing alcohol.

[0038] [2-3] The glycerol, the catalyst, and the C １－６ and an alcohol to obtain a catalyst mixture; and mixing the catalyst mixture with a fatty acid composition containing the ethyl ester of the fatty acid, and subjecting the resulting mixture to the reaction.

[0039] [2-4] The method according to [2-3], wherein mixing the catalyst mixture and the fatty acid composition comprises adding the fatty acid composition to the catalyst mixture.

[0040] [2-5] The method according to [2-4], wherein the catalyst mixture is mixed at 30°C to 50°C, and then the fatty acid composition is added.

[0041] [2-6] The method according to any one of [2-1] to [2-5], wherein the catalyst is an alkaline catalyst.

[0042] [2-7] The method according to any one of [2-1] to [2-6], wherein the reaction is carried out at 40°C to 160°C.

[0043] [2-8] The method according to any one of [2-1] to [2-7], wherein the reaction is carried out at 3000 Pa or less.

[0044] [2-9] The fatty acid composition and the C １－６ The method according to any one of [2-1] to [2-8], wherein the weight ratio of alcohol is 2:1 to 1:10.

[0045] [2-10] The C relative to the glycerol １－６ The method according to any one of [2-1] to [2-9], wherein the molar ratio of alcohol is 1:10 or more and 1:100 or less.

[0046] [2-11] The method according to any one of [2-1] to [2-10], wherein the catalyst is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium alcoholate, or potassium alcoholate.

[0047] [2-12] The method according to any one of [2-1] to [2-11], wherein the reaction is carried out at 1000 Pa or less.

[0048] [2-13] The method according to any one of [2-1] to [2-12], wherein the fatty acid composition is derived from marine oil or microbial oil.

[0049] [2-14] The method according to any one of [2-1] to [2-13], wherein the fatty acid composition contains 25% by weight or more of ethyl ester of PUFA.

[0050] [2-15] The above C １－６ The method according to any one of [2-1] to [2-14], wherein the alcohol is ethanol.

[0051] [2-16] The method according to any one of [2-1] to [2-15], wherein the fatty acid composition contains a total of 25% by weight or more of ethyl ester of EPA and ethyl ester of DHA.

[0052] [2-17] The method according to any one of [2-1] to [2-16], wherein the molar ratio of the glycerol to the ethyl ester of the fatty acid is 1:3 to 1:9.

[0053] [2-18] The method for producing an oil or fat composition according to any one of [2-1] to [2-17], wherein, among the fatty acids that are constituent fatty acids of acylglycerols in the oil or fat composition, three or more fatty acids are present in a weight ratio of 5 wt % or more relative to all constituent fatty acids, at least one of the fatty acids present in a weight ratio of 5 wt % or more is a PUFA, for all of the fatty acids present in a weight ratio of 5 wt % or more, the ratio of the weight ratio in all constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil or fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

[0054] [2-19] The method according to [2-18], wherein the PUFA in the oil and fat composition contains ω3 highly unsaturated fatty acids.

[0055] [2-20] The production method according to [2-18] or [2-19], wherein the PUFA in the oil or fat composition contains EPA or DHA.

[0056] [2-21] The production method according to any one of [2-18] to [2-20], wherein, among the constituent fatty acids of the acylglycerol, all fatty acids present in a weight ratio of 1% by weight or more relative to the total constituent fatty acids have a weight ratio of 7:10 or more to 13:10 or less at the sn2 position.

[0057] [2-22] The manufacturing method according to any one of [2-18] to [2-21], wherein the content of oligomers in the oil and fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area% or less.

[0058] [2-23] The method according to any one of [2-18] to [2-22], wherein the oil or fat composition contains triacylglycerol in an amount of 50% by weight or more.

[0059] [2-24] The method according to any one of [2-18] to [2-23], wherein the oil or fat composition further contains 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

[0060] [2-25] The method according to [2-24], wherein the oil or fat composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

[0061] [2-26] The method according to any one of [2-18] to [2-25], wherein the constituent fatty acids contain PUFAs in a proportion of 25% by weight or more.

[0062] [2-27] The method according to [2-18] to [2-26], wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

[0063] [3-1] An oil or fat composition containing an acylglycerol, wherein the acylglycerol contains a triacylglycerol, wherein three or more fatty acids are present in a weight ratio of 5% by weight or more relative to all constituent fatty acids of the acylglycerol, at least one of the fatty acids present in a weight ratio of 5% by weight or more is a PUFA, and for all of the fatty acids present in a weight ratio of 5% by weight or more, the ratio of the weight ratio of each fatty acid in all constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil or fat composition measured according to the measurement method of EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

[0064] [3-2] The oil and fat composition according to [3-1], wherein the PUFA contains an ω3 highly unsaturated fatty acid.

[0065] [3-3] The oil or fat composition according to [3-1] or [3-2], wherein the PUFA contains EPA or DHA.

[0066] [3-4] The oil and fat composition according to any one of [3-1] to [3-3], wherein, among the constituent fatty acids of the acylglycerol, all fatty acids present in a weight ratio of 1% by weight or more relative to the total constituent fatty acids have a weight ratio of 7:10 or more to 13:10 or less at the sn2 position.

[0067] [3-5] The oil and fat composition according to any one of [3-1] to [3-4], wherein the content of oligomers in the oil and fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area % or less.

[0068] [3-6] The oil or fat composition according to any one of [3-1] to [3-5], wherein the oil or fat composition contains triacylglycerol in an amount of 50% by weight or more.

[0069] [3-7] The oil or fat composition according to any one of [3-1] to [3-6], further containing 5 wt % or more, or 10 wt % or more, and / or 40 wt % or less of diacylglycerol.

[0070] [3-8] The oil or fat composition according to [3-7], wherein the oil or fat composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

[0071] [3-9] The oil and fat composition according to any one of [3-1] to [3-8], wherein the constituent fatty acids contain PUFAs in a proportion of 25% by weight or more.

[0072] [3-10] The oil and fat composition according to any one of [3-1] to [3-9], wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

[0073] [3-11] An oil or fat composition produced by the method according to [1-1] to [1-26].

[0074] [3-12] Use of the oil or fat composition according to any one of [3-1] to [3-11] in the production of a food product, a pharmaceutical product, or a quasi-drug product.

[0075] [3-13] A food, a medicine, or a quasi-drug, comprising the oil or fat composition according to any one of [3-1] to [3-11].

[0076] [4-1] An oil or fat composition containing an acylglycerol, wherein the acylglycerol comprises a triacylglycerol, wherein the triacylglycerol is a reconstituted triacylglycerol, and wherein the content of oligomers in the oil or fat composition as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

[0077] [4-2] The oil and fat composition according to [4-1], wherein at least one of the constituent fatty acids of the acylglycerol is a PUFA.

[0078] [4-3] The oil and fat composition according to [4-2], wherein the PUFA contains an ω3 highly unsaturated fatty acid.

[0079] [4-4] The oil or fat composition according to [4-2] or [4-3], wherein the PUFA contains EPA or DHA.

[0080] [4-5] The oil or fat composition according to any one of [4-1] to [4-4], wherein the content of oligomers in the oil or fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area % or less.

[0081] [4-6] The oil or fat composition according to any one of [4-1] to [4-5], wherein the oil or fat composition contains triacylglycerol in an amount of 50% by weight or more.

[0082] [4-7] The oil or fat composition according to any one of [4-1] to [4-6], further comprising 5 wt % or more, or 10 wt % or more, and / or 40 wt % or less of diacylglycerol.

[0083] [4-8] The oil or fat composition according to [4-7], wherein the oil or fat composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

[0084] [4-9] The oil and fat composition according to any one of [4-1] to [4-8], wherein the constituent fatty acids of the acylglycerol contain PUFA in a proportion of 25% by weight or more.

[0085] [4-10] The oil or fat composition according to any one of [4-1] to [4-8], wherein the constituent fatty acids of the acylglycerol contain EPA and DHA in a total amount of 25% by weight or more.

[0086] [4-11] An oil or fat composition produced by the method according to [1-1] to [1-26].

[0087] [4-12] Use of the oil or fat composition according to any one of [4-1] to [4-11] in the production of a food product, a pharmaceutical product, or a quasi-drug product.

[0088] [4-13] A food, a medicine, or a quasi-drug, comprising the oil or fat composition according to any one of [4-1] to [4-11].

[0089] According to the present disclosure, an oil and fat composition containing TAG, which contains a high concentration of a target highly unsaturated fatty acid as a constituent fatty acid, and which has a low oligomer content, can be efficiently produced by a low-temperature reaction in a short time.

[0090] The present disclosure will be described in more detail below.

[0091] The following abbreviations may be used herein: DHA: docosahexaenoic acid (all cis-docosa-4,7,10,13,16,19-hexaenoic acid) EPA: eicosapentaenoic acid (all cis-eicosa-5,8,11,14,17-pentaenoic acid) TAG: triacylglycerol DAG: diacylglycerol MAG: monoacylglycerol Oil / Fat Composition In one embodiment of the present invention, the oil / fat composition contains acylglycerol. As used herein, "acylglycerol" is a general term for fatty acid esters of glycerol and includes monoacylglycerol, diacylglycerol, and triacylglycerol. In one embodiment of the present invention, acylglycerol refers to triacylglycerol, diacylglycerol, and / or monoacylglycerol.

[0092] In one embodiment of the present invention, the oil and fat composition contains triacylglycerol. As used herein, "triacylglycerol" refers to a compound in which one molecule of glycerol is ester-bonded with three molecules of fatty acid, and is also referred to as a triglyceride or triacylglyceride. In one embodiment of the present invention, the triacylglycerol may contain polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids, and / or saturated fatty acids as constituent fatty acids. The binding positions of the fatty acids are classified into sn1, sn2, and sn3 positions by a stereospecifically numbered system based on the Fischer projection of the glycerol skeleton.

[0093] The oil and fat composition in one embodiment of the present invention may contain diacylglycerol. As used herein, "diacylglycerol" refers to a compound in which two molecules of fatty acid are ester-bonded to one molecule of glycerol, and is also referred to as a diglyceride or diacylglyceride. In one embodiment of the present invention, the diacylglycerol may contain polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids, and / or saturated fatty acids as constituent fatty acids. The binding positions of the fatty acids are not particularly limited, and may be any two selected from the sn1, sn2, and sn3 positions of glycerol.

[0094] The oil and fat composition in one embodiment of the present invention may contain monoacylglycerol. As used herein, "monoacylglycerol" refers to a compound in which one molecule of fatty acid is ester-bonded to one molecule of glycerol, and is also referred to as a monoglyceride or monoacylglyceride. In one embodiment of the present invention, the monoacylglycerol may contain polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids, and / or saturated fatty acids as constituent fatty acids. The binding position of the fatty acid is not particularly limited, and is any one selected from the sn1, sn2, and sn3 positions of glycerol.

[0095] As used herein, the term "fatty acid" refers to aliphatic monocarboxylic acids of various chain lengths. For example, C １－６ fatty acid, C １６－２４ Contains fatty acids. １－６ Fatty acids include propionic acid, n-butyric acid, n-valeric acid, isovaleric acid, formic acid, and acetic acid. Fatty acid structures can be represented by a simple "X:Y" notation, where X is the total number of carbon atoms in the particular fatty acid and Y is the number of double bonds. For example, a saturated fatty acid with 20 carbon atoms is represented as "C20:0," a monounsaturated fatty acid with 18 carbon atoms is represented as "C18:1," and arachidonic acid can be represented as "C20:4,n-6." The "n-" indicates the position of the double bond beginning from the methyl end of the fatty acid; for example, "n-6" indicates that the double bond begins at the sixth position from the methyl end of the fatty acid. Alternatively, "ω-" or "ω" can be used instead of "n-." "ω3" indicates that the double bond begins at the third position from the methyl end of the fatty acid. 5,11-hexadecadienoic acid can be represented as "C16:2(5,11)." The numbers in the parentheses () indicate the position of the double bond from the carboxy terminal, for example, C16:2(5,11) indicates that there are two double bonds, one between the 5th and 6th carbons and the other between the 11th and 12th carbons from the carboxy terminal. This method is well known to those skilled in the art, and fatty acids represented according to this method can be easily identified by those skilled in the art.

[0096] Fatty acids are carboxylic acids with an aliphatic chain, which can be either saturated or unsaturated. Unsaturated fatty acids can be either monounsaturated or polyunsaturated. Fatty acids are usually produced industrially by hydrolysis of triglycerides or phospholipids from natural sources. Some are also produced synthetically. Regardless of the method of production, purification methods are required to obtain a pure product for food, cosmetic, or industrial use.

[0097] As used herein, the term "polyunsaturated fatty acid" refers to a fatty acid having more than one double bond. As used herein, polyunsaturated fatty acids are sometimes referred to as PUFAs. Polyunsaturated fatty acids may be, for example, fatty acids having 16 to 24 carbon atoms. Polyunsaturated fatty acids may be, for example, fatty acids having 3 to 6 double bonds. Examples of highly unsaturated fatty acids include α-linolenic acid (C18:3,n-3), γ-linolenic acid (C18:3,n-6), stearidonic acid (C18:4,n-3), dihomo-γ-linolenic acid (C20:3,n-6), arachidonic acid (C20:4,n-6), eicosapentaenoic acid (C20:5,n-3), clupanodonic acid (C22:5,n-3), docosapentaenoic acid (C22:5,n-6), and docosahexaenoic acid (C22:6,n-3). Among these, ω3 highly unsaturated fatty acids, in which the double bond begins at the third position counting from the methyl end of the fatty acid, include α-linolenic acid, stearidonic acid, eicosapentaenoic acid, clupanodonic acid, docosapentaenoic acid, and docosahexaenoic acid.

[0098] The oil and fat composition in one embodiment of the present invention is a composition containing eicosapentaenoic acid "C20:5,n-3" (hereinafter also referred to as EPA), docosahexaenoic acid "C22:6,n-3" (hereinafter also referred to as DHA), 5,11-hexadecadienoic acid "C16:2(5,11)", 9,12-hexadecadienoic acid "C16:2(9,12)", 5, ... -Hexadecatrienoic acid "C16:3 (5,9,12)", n-3 hexadecatetraenoic acid "C16:4,n-3", linoleic acid "C18:2,n-6", alpha linolenic acid "C18:3,n-3", gamma linolenic acid "C18:3,n-6", pinolenic acid "C18:3 (5,9,12)", eleostearic acid "C18:3 (9,11, 13), stearidonic acid "C18:4,n-3", nonadecyltetraenoic acid "C19:4", eicosadienoic acid "C20:2,n-6", eicosatrienoic acid "C20:3,n-3", dihomo-γ-linolenic acid "C20:3,n-6" (hereinafter also referred to as DGLA), mead acid "C20:3,n-9", n-3 eicosatetraenoic acid The acylglycerol-constituting fatty acids may be one or a combination of two or more highly unsaturated fatty acids selected from the group consisting of arachidonic acid "C20:4,n-3", arachidonic acid "C20:4,n-6" (hereinafter also referred to as ARA), bosseopentaenoic acid "C20:5 (5,8,10,12,14)", heneicosapentaenoic acid "C21:5,n-3", docosadienoic acid "C22:2,n-6", adrenic acid "C22:4,n-6", osbond acid "C22:5,n-6", clupanodonic acid "C22:5,n-3", tetracosapentaenoic acid "C24:5,n-3", and herring acid "C24:6,n-3". Among these, ω3 highly unsaturated fatty acids include EPA, DHA, n-3 hexadecatetraenoic acid, α-linolenic acid, stearidonic acid, eicosatrienoic acid, n-3 eicosatetraenoic acid, heneicosapentaenoic acid, sardine acid, tetracosapentaenoic acid, and herring acid.In one embodiment of the present invention, in addition to the acylglycerol-constituting fatty acids selected from the aforementioned highly unsaturated fatty acids, the oil and fat composition may contain, as the acylglycerol-constituting fatty acids, one fatty acid or a combination of two or more fatty acids selected from the following: monounsaturated fatty acids such as crotonic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, and nervonic acid; propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, and carboceric acid. saturated fatty acids such as hexatriacontylic acid, hexatriacontylic acid, octatriacontylic acid, nonatriacontylic acid, and tetracontylic acid;

[0099] As used herein, the term "constituent fatty acid" refers to a fatty acid that constitutes an acylglycerol. More specifically, it refers to a fatty acid species that is ester-linked to the glycerol backbone of triacylglycerol, diacylglycerol, or monoacylglycerol.

[0100] In one embodiment of the present invention, the oil or fat composition contains acylglycerol containing three or more fatty acids, each of which is present in a weight ratio of 5% by weight or more relative to the total constituent fatty acids, and at least one of the fatty acids present in a weight ratio of 5% by weight or more is a PUFA. In one embodiment of the present invention, the PUFA includes an ω3 highly unsaturated fatty acid. In one embodiment of the present invention, the PUFA includes EPA and / or DHA.

[0101] In one aspect of the present invention, the oil and fat composition contains an acylglycerol containing three or more fatty acids, each present at a weight ratio of 5 wt% or more relative to the total constituent fatty acids, and the ratio of the weight ratio of all of the fatty acids present at a weight ratio of 5 wt% or more relative to the total constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less. Specifically, the ratios of all fatty acids present at 5 wt% or more, 3 wt% or more, or 1 wt% or more relative to the total constituent fatty acids are 7:10, 6:10, or 5:10 or more and / or 13:10, 15:10, or 17:10 or less. In one aspect of the present invention, the ratio of the weight ratio of all of the constituent fatty acids contained in the oil and fat composition relative to the weight ratio at the sn2 position is 5:10 or more and 17:10 or less. Specifically, the ratio is greater than or equal to 7:10, 6:10 or 5:10 and / or less than or equal to 13:10, 15:10 or 17:10, respectively.

[0102] In one embodiment of the present invention, the oil and fat composition contains highly unsaturated fatty acids as constituent fatty acids in a proportion of 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more, and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99% of the total oil and fat composition.

[0103] In one embodiment of the present invention, the oil and fat composition contains highly unsaturated fatty acids as constituent fatty acids in a proportion of 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more, and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99% of the total constituent fatty acids.

[0104] In one embodiment of the present invention, the oil or fat composition contains EPA and DHA in total at a ratio of 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more of the total constituent fatty acids, and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99%.

[0105] In one embodiment of the present invention, the oil or fat composition contains 50% by weight or more, 60% by weight or more, or 70% by weight or more of triacylglycerols.

[0106] In one embodiment of the present invention, the oil or fat composition contains 5 wt % or more, 10 wt % or more, or 20 wt % or more, and / or 30 wt % or less, 40 wt % or less of diacylglycerol.

[0107] In one embodiment of the present invention, the oil or fat composition contains 0 wt %, 1 wt % or less, or 5 wt % or less monoacylglycerol, where 0 wt % means that the MAG is below the detection limit when the oil or fat composition is measured using an Iatroscan MK-6 (Mitsubishi Iatron).

[0108] In one embodiment of the present invention, the oil or fat composition contains a reduced amount of oligomers. As used herein, oligomer refers to a compound having a molecular weight greater than that of TAG in the oil or fat composition. As used herein, oligomers include, for example, dimers consisting of two monomers, trimers consisting of three monomers, and tetramers consisting of four monomers. In one embodiment of the present invention, the content of oligomers in the oil or fat composition is 0.8 area% or less, 0.7 area% or less, 0.6 area% or less, 0.5 area% or less, or 0.4 area% or less, as determined by analysis based on the measurement method of EUROPEAN PHARMACOPOEIA 8.0.

[0109] As used herein, the term "re-esterified triacylglycerol" (rTG: re-esterified triacylglycerol) refers to triacylglycerol obtained from fatty acids or fatty acid esters and glycerol by a synthetic method such as esterification or transesterification. Reconstituted triacylglycerol is distinguished from triacylglycerols contained in raw materials such as marine oil, microbial oil, and vegetable oil (triacylglycerol derived from natural sources), and is a triacylglycerol prepared by changing the binding position of the fatty acid and / or the fatty acid composition. Reconstituted triacylglycerol is, for example, a triacylglycerol obtained from raw materials such as marine oil, microbial oil, and vegetable oil, or a C-terminal fatty acid thereof. １－６ Alcohol esters and glycerol or C １－６The reconstituted triacylglycerol is obtained by reacting fatty acid glycerol esters. In one embodiment of the present invention, the reconstituted triacylglycerol contains, as constituent fatty acids, fatty acid species derived from a raw material containing fats and oils. In one embodiment of the present invention, the reconstituted triacylglycerol has the characteristic that the binding positions of the constituent fatty acids are random, and that the specificity of the constituent fatty acids between the sn1, sn2, and sn3 positions is lower than that of the acylglycerol constituting the raw material containing fats and oils. Specifically, for all of the constituent fatty acids contained in an amount of 5% by weight or more, 3% by weight or more, or 1% by weight or more of the total constituent fatty acids, the weight ratio of the respective constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 7:10, 6:10, or 5:10 or more and / or 13:10, 15:10, or 17:10.

[0110] In one embodiment of the present invention, １－６ Glycerol or C in the presence of an alcohol and a catalyst １－６ Fatty acid glycerol ester and a fatty acid or its C １－６ By subjecting a fatty acid composition containing an alcohol ester to a reaction, an oil or fat composition containing acylglycerol, wherein the acylglycerol includes triacylglycerol, can be obtained.

[0111] In one embodiment of the present invention, C １－６ The removal of alcohol means that the C in the reaction system is removed in order to shift the reaction equilibrium toward triacylglycerol production. １－６ This means reducing the alcohol concentration compared to before the reaction. It is sufficient to reduce it to the extent that the reaction equilibrium is shifted. １－６ The alcohol concentration is not particularly limited.

[0112] In one embodiment of the present invention, mixing means placing two or more components in the same system. If they are in the same system, the state of the mixed components is not particularly limited, and they may be in a homogeneous state or a heterogeneous state.

[0113] In one embodiment of the invention, the reaction is an esterification reaction. In one embodiment of the invention, the reaction is a transesterification reaction. In one embodiment of the invention, the reaction is a fatty acid or its C１－６ After adding the fatty acid composition containing the alcohol ester, the reaction is carried out by mixing and heating at room temperature or above. In one embodiment of the present invention, the reaction is carried out by heating the fatty acid composition containing the alcohol ester under reduced pressure to shift the equilibrium of the esterification reaction / transesterification reaction. １－６ This is carried out while distilling off the alcohol under reduced pressure. In one embodiment of the present invention, the triacylglycerol may contain a triacylglycerol whose three constituent fatty acids are derived from a fatty acid composition.

[0114] In one aspect of the present invention, the oil and fat composition containing the obtained acylglycerol, wherein the acylglycerol includes triacylglycerol, can be explained by referring to the explanation of the "Oil and fat composition" above as appropriate, and therefore the explanation of the "Production method" will be omitted.

[0115] In one embodiment of the present invention, the reaction is carried out under a pressure of 5000 Pa or less, 3000 Pa or less, 1000 Pa or less, or 300 Pa or less. In one embodiment of the present invention, the reaction is carried out at a temperature of 40 to 200°C, 40 to 180°C, 40 to 160°C, 40 to 140°C, or 70 to 120°C. When reducing the pressure during the reaction, the pressure in the system is gradually reduced to about 3000 Pa to prevent bumping. １－６ After confirming that about 90% of the alcohol, for example, ethanol, has been distilled off, the pressure in the system is reduced to 3000 Pa or less, 1000 Pa or less, or 300 Pa or less, and the system is heated at 40 to 160°C, 40 to 140°C, or 70 to 120°C while maintaining the pressure. In one embodiment of the present invention, the reaction time is not particularly limited, and the reaction is continued until the TAG and / or DAG reach the desired ratio. Specifically, the reaction is carried out for 2 to 4 hours, 2 to 6 hours, or 2 to 10 hours.

[0116] In one embodiment of the present invention, in the esterification reaction / transesterification reaction using a catalyst such as an alkali catalyst, the bonding positions of the constituent fatty acids are random.

[0117] Examples of the alkali catalyst in one embodiment of the present invention include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, and alkali metal alcoholates such as lithium alcoholate, sodium alcoholate, and potassium alcoholate. １－６ Examples of the alkali catalyst include alcoholates. Specifically, examples of the alkali catalyst include ethanolates. In one embodiment of the present invention, the catalyst such as the alkali catalyst can be used as granules or a solution. The alkali catalyst solution can be, for example, an aqueous solution, C １－６ Examples of suitable solutions include alcohol solutions, and more specifically, aqueous or ethanol solutions of alkali metal hydroxides such as sodium hydroxide.

[0118] In one embodiment of the present invention, the amount of the catalyst is not particularly limited, but is, for example, 7.5 mol%, 10 mol%, 12.5 mol%, or 15 mol% or less, and / or 0.5 mol%, 1.0 mol%, 2.0 mol%, 2.5 mol%, or 7.5 mol% or more relative to the fatty acid composition.

[0119] In one embodiment of the present invention, C １－６ Fatty acid glycerol esters are ester bonds formed between the three hydroxyl groups of glycerol and fatty acids with 1 to 6 carbon atoms, and there are three types: mono-, di-, and triesters. １－６ Fatty acids are as described above. Glycerol C １－６ Also called fatty acid esters.

[0120] In one embodiment of the present invention, glycerol or C １－６ Fatty acid glycerol ester and C １－６ The molar ratio of alcohol is 1:10 to 1:20, 1:5 to 1:20, or 1:2 to 1:100. Here, the molar ratio is determined based on the amount of glycerol or C １－６ Molar number of fatty acid glycerol esters": "C １－６ "Number of moles of alcohol".

[0121] In one embodiment of the present invention, alcohols such as C １－６An alcohol is added. As used herein, an alcohol is a monohydric straight-chain or branched alkyl alcohol. １－６ The alcohol is a monovalent linear or branched alkyl alcohol having 1 to 6 carbon atoms, and specific examples thereof include methanol, ethanol, linear or branched propanol, linear or branched butanol, linear or branched pentanol, linear or branched hexanol, and mixtures thereof. １－６ The alcohol may be, for example, an alcohol having 1 to 3 carbon atoms, such as ethanol. １－６ The weight ratio of the alcohol is 2:1 to 1:10, 4:1 to 1:10, or 10:1 to 1:10. Here, the weight ratio is determined based on the weight of the fatty acid composition to be mixed before the reaction: C １－６ "weight of alcohol".

[0122] In one embodiment of the present invention, the catalyst, glycerol or C １－６ Fatty acid glycerol esters and C １－６ After the alcohol is mixed to obtain the catalyst mixture, the catalyst mixture and the fatty acid composition can be mixed and subjected to reaction. In one embodiment of the present invention, the catalyst mixture comprises a catalyst, glycerol or C １－６ Fatty acid glycerol esters and C １－６ In one embodiment of the present invention, the catalyst mixture comprises a catalyst, glycerol or C １－６ Fatty acid glycerol esters and C １－６ The catalyst mixture can be obtained by mixing the alcohol at room temperature or higher, for example, at 30° C. to 50° C., or at 40° C. In one embodiment of the present invention, the state of the catalyst mixture is not particularly limited, but examples thereof include a dispersed state such as a solution or emulsion.

[0123] In one embodiment of the present invention, a fatty acid or its C １－６The fatty acid composition containing alcohol esters can be obtained from raw materials containing fats and oils obtained from marine organisms, microorganisms, and plants. Examples of raw materials containing fats and oils include marine oils, microbial oils, and vegetable oils. Marine oils can include fats and oils obtained from marine organisms. Specifically, marine oils include fish oils such as sardine oil, tuna oil, bonito oil, menhaden oil, cod liver oil, herring oil, capelin oil, and salmon oil, as well as krill oil. Microbial oils include fats and oils produced by microorganisms such as Mortierella, Penicillium, Aspergillus, Rhodotorula, and Fusarium. Vegetable oils include, for example, borage oil, rhododendron oil, evening primrose oil, perilla oil, flax oil, soybean oil, and rapeseed oil.

[0124] In one embodiment of the present invention, a fatty acid or its C １－６ The fatty acid composition containing alcohol esters can be obtained by distilling a raw material containing fats and oils.

[0125] In one embodiment of the present invention, a fatty acid or its C １－６ The fatty acid composition containing alcohol esters may contain fatty acids obtained by decomposing a raw material containing fats and oils into free fatty acids by hydrolysis using water, or may contain fatty acids obtained by decomposing a raw material containing fats and oils into free fatty acids by hydrolysis using water. １－６ By alcoholysis with alkyl alcohol, C １－６ It may contain alcohol esters broken down into alkyl esters. １－６ Examples of alcohol esters include ethyl esters.

[0126] In one embodiment of the present invention, the fatty acid composition contains highly unsaturated fatty acids or their C-type fatty acids in a proportion of 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more, and / or less than 50%, less than 55%, less than 60%, less than 65%, 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99% of the total fatty acid composition. １－６ Contains alcohol esters.

[0127] In one embodiment of the present invention, the fatty acid composition comprises total fatty acids or C １－６ and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99% of the alcohol ester is highly unsaturated fatty acid or its C １－６ Contains alcohol esters.

[0128] In one embodiment of the present invention, the fatty acid composition contains ethyl esters of EPA and ethyl esters of DHA in total at a ratio of 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, or 95% or more, and / or less than 50%, less than 55%, less than 60%, less than 65%, less than 70%, less than 75%, less than 80%, less than 85%, less than 90%, less than 95%, less than 97%, less than 98%, or less than 99% of the total fatty acid composition.

[0129] In one embodiment of the present invention, the molecular weight of the fatty acid composition is determined by GC of the fatty acid or its C １－６The weight percentage of each fatty acid in the alcohol ester is calculated, and the average molecular weight is calculated based on this value and the molecular weight of each fatty acid. １－６ The amount of substance of the alcohol ester can be calculated.

[0130] In one embodiment of the present invention, the reaction mixture comprises １－６ Glycerol or C in the presence of an alcohol and a catalyst １－６ Fatty acid glycerol ester and a fatty acid or its C １－６ The reaction mixture can be obtained by mixing a catalyst mixture with a fatty acid composition containing an alcohol ester. In one embodiment of the present invention, the reaction mixture can be obtained by mixing the catalyst mixture with a fatty acid composition. In one embodiment of the present invention, the reaction mixture can be obtained by adding a fatty acid composition to the catalyst mixture. In one embodiment of the present invention, the reaction mixture includes a mixture during the reaction and a mixture before post-treatment after the reaction. In one embodiment of the present invention, the state of the reaction mixture is not particularly limited, but examples include a dispersed state such as a solution or an emulsion.

[0131] Without being limited to a particular theory, in one embodiment, the reaction mechanism of the present disclosure is assumed to be as follows: Glycerol and fatty acid C under alkali catalysis １－６ In the esterification reaction of alcohol esters, the anion generated by ionization of the alkali catalyst removes a proton from glycerol to generate a glycerate anion. This glycerate anion is then converted into fatty acid C. １－６ Nucleophilic attack occurs on the carboxyl carbon of the alcohol ester, and via a tetrahedral intermediate, an alcoholate anion is eliminated to produce monoacylglycerol (hereinafter also referred to as MAG). Next, the anion produced by ionization of the alkali catalyst or the alcoholate anion produced in the above reaction removes a proton from the hydroxyl group of MAG to produce a glycerate anion again, and fatty acid C １－６ Diacylglycerol (hereinafter also referred to as DAG) is produced by reacting in the same way as alcohol esters. Glycerate anions are again formed from DAG in the same way, and fatty acid C １－６The reaction with alcohol ester produces TAG. Since the series of esterification reactions is an equilibrium reaction, the alcoholate anion produced as a by-product can be converted to C by the reaction at reduced pressure or high temperature. １－６ The reaction rate can be increased by removing the alcohol from the system and shifting the reaction equilibrium toward glycerol production. On the other hand, the reaction at low temperatures below 160°C is １－６ The reaction rate is reduced due to the poor efficiency of alcohol removal. In addition, the lack of thermal energy leads to a lack of energy for molecular motion, which reduces the rate of glycerate anion production and also reduces the reaction rate between glycerate anion and fatty acid C. １－６ The contact efficiency of the alcohol ester is low, and the reaction does not proceed easily. In fact, when the reaction was carried out at 160°C or less using an alkaline catalyst, the TAG production rate was low even after a certain period of time had passed (Comparative Examples 2 and 3).

[0132] In one embodiment of the present disclosure, a certain amount or more of C １－６ By mixing alcohol with an alkaline catalyst, C １－６ These C １－６ Since alcoholate anions are more basic than hydroxide ions in the Lewis definition, it is thought that the deprotonation reaction of glycerol occurs more easily, making it easier to generate glycerate anions, which are the true catalyst. １－６ Alcoholate anion and fatty acid C １－６ Repeated nucleophilic substitution of alcohol esters results in fatty acid C １－６ It is thought that the electrophilicity of the carbonyl carbon of the alcohol ester increases, increasing the reactivity. １－６ While alcohol esters have low hydrophilicity, glycerate anions have high hydrophilicity and high viscosity, so they tend to settle in the bottom layer. １－６ Although the contact efficiency between alcohol esters and glycerate anions is low, this method requires a certain amount of C １－６ Addition of alcohol converts the glycerate anion to fatty acid C. １－６It is thought that the reaction rate of the esterification reaction can be increased because the contact efficiency increases as the alcohol ester becomes more easily dispersed. １－６ This enables the esterification reaction of alcohol esters and the production of re-esterified TAG with little thermal history.

[0133] In one embodiment of the present disclosure, C different from the above reaction mechanism description １－６ Alcohol, catalyst, glycerol or fatty acid C １－６ In the case of an esterification reaction / transesterification reaction using a glycerol ester and / or a fatty acid composition, the reaction is thought to proceed according to a similar reaction mechanism.

[0134] In this specification, the amount of each constituent fatty acid in an oil or fat composition means, unless otherwise specified, the total amount of the plurality of fatty acid species present in the oil or fat composition when the oil or fat composition contains a plurality of fatty acid species corresponding to each constituent fatty acid. In this specification, the content (%) of each constituent fatty acid in an oil or fat composition means, unless otherwise specified, the total content of the plurality of fatty acid species present in the oil or fat composition when the oil or fat composition contains a plurality of fatty acid species corresponding to each constituent fatty acid.

[0135] In this specification, the amount of each component in the fatty acid composition means, unless otherwise specified, the total amount of the plurality of substances present in the fatty acid composition when the fatty acid composition contains a plurality of substances corresponding to each component. In this specification, the content (%) of each component in the fatty acid composition means, unless otherwise specified, the total content of the plurality of substances present in the fatty acid composition when the fatty acid composition contains a plurality of substances corresponding to each component.

[0136] In this specification, the content of fatty acid species in a composition is determined based on the fatty acid composition unless otherwise specified. The fatty acid composition can be determined by a conventional method. Specifically, when the fatty acid species in the composition to be measured is a fatty acid C such as acylglycerol, １－６ In the case of other than alcohol esters, the fatty acid species to be measured is C １－６Fatty acid C obtained by esterification with alcohol using a catalyst １－６ The fatty acid species in the composition to be measured is fatty acid C. １－６ In the case of alcohol esters, the fatty acid to be measured is used as is. １－６ Alcohol esters are used as samples and analyzed using gas chromatography. Peaks corresponding to each fatty acid are identified in the resulting gas chromatography chart, and the peak area of ​​each fatty acid is determined using the Agilent ChemStation integration algorithm. The peak area is the ratio (area %) of the peak area of ​​each component to the total peak area in a chart obtained by analyzing fats and oils composed of various fatty acids using gas chromatography, thin-layer chromatography / flame ionization detector (TLC / FID), or other methods, and indicates the content ratio of the component at that peak. The area % values ​​obtained by the above-mentioned measurement method can be used interchangeably as the weight % values ​​of each fatty acid relative to the total weight of fatty acids in the sample. See the Japan Oil Chemists' Society (JOCS) Standard Test Methods for the Analysis of Fats, Oils, and Related Materials, 2013 Edition, 2.4.2.1-2013 Fatty Acid Composition (FID Constant Temperature Gas Chromatography) and 2.4.2.2-2013 Fatty Acid Composition (FID Programmed Temperature Gas Chromatography). The weight ratio of each fatty acid to all constituent fatty acids is the same as the value obtained as the ratio (area %) of the peak area of ​​each component to the total peak area in the analyzed chart described above.

[0137] Use Forms In one embodiment of the present disclosure, the uses of the oil and fat composition include, for example, foods, pharmaceuticals, and quasi-drugs, with foods being preferred. Foods include health foods, dairy products, soft drinks, edible oils and fats, pet food and beverages, and livestock feed. In this specification, "health foods" refers to foods that claim to be healthy and / or foods intended to maintain or promote health, including dietary supplements, foods for specified health uses, foods with functional claims, and supplements. Health foods are preferred, with supplements being particularly preferred. Supplements refer to products in the form of tablets, capsules, or gummies containing a concentrated oil and fat composition. The content of the oil and fat composition in the supplement is not particularly limited, but may be 25% by weight or more, 50% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more, and / or 98% by weight or less, 95% by weight or less, or 90% by weight or less. In one embodiment of the present disclosure, the food, pharmaceutical, or quasi-drug may be in any form suitable for administration to an animal body, such as a human body, but is preferably in an oral administration form. Oral administration forms may be in solid forms (e.g., tablets, pills, granules, sugar-coated tablets, hard capsules, soft capsules, or effervescent formulations of powder or tablets) or liquid forms (e.g., solutions, emulsions, or suspensions). In one embodiment of the present disclosure, the food, pharmaceutical, or quasi-drug may contain antioxidants, gelling agents, excipients, coating agents, flavoring agents, fragrances, preservatives, emulsifiers, pH adjusters, buffers, colorants, etc., when formulated into solid or liquid forms. In one embodiment of the present disclosure, the food, pharmaceutical, or quasi-drug may contain an antioxidant. Examples of antioxidants include dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), propyl gallate, gallic acid, ascorbic acid esters such as ascorbyl palmitate, and tocopherols. At least one selected from these may be contained in an effective amount as an antioxidant.

[0138] Ranges are provided herein by numerical values ​​preceded by the term "about." The term "about" is used herein to provide literal support for the exact number it precedes as well as a number that is close to or approximately the number preceded by the term. In determining whether a number is close to or approximately a specifically stated number, an unstated number that is close to or approaching the stated number can be a number that provides a substantial equivalent of the specifically stated number in the context in which it is given. In some embodiments, about can refer to ±5%, ±2.5%, or ±1% of the number to which it refers.

[0139] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although any methods and materials similar or equivalent to those described herein can also be used in the practice or testing of the present invention, representative exemplary methods and materials are described herein.

[0140] The present invention will now be further described with reference to examples, but the present invention is not limited to these examples.

[0141] In the examples, percentages are by weight unless otherwise specified.

[0142] The TAG ratio, oligomer content, and fatty acid composition in the oil and fat composition were analyzed by the following methods.

[0143] <Analysis of Acylglycerol Ratio (TLC-FID)> 10 μL of sample was dissolved in 990 μL of tetrahydrofuran (THF), and 1 μL of the solution was spotted at the origin of an Iatroscan Chroma Rod. After drying, the sample was developed with chloroform:methanol = 95:5 (v / v) for 5 minutes. After drying again, the sample was developed with hexane:diethyl ether:acetic acid = 90:10:1 (v / v / v) for 30 minutes. After drying, the Chroma Rod was placed in an Iatroscan (MK-6, Mitsubishi Iatron) and analyzed. The area percentages of the EE, TAG, DAG, and MAG peaks were calculated relative to the total area value of the peaks derived from the sample on the chromatograph. In FID detection, carbon in the sample was oxidized and ionized by a hydrogen flame, and the components were detected by electrostatically collecting these ions with a collector. Therefore, the peak area values ​​reflect the mass of the lipid species. In this specification, the area percentage of each lipid species calculated by TLC-FID is expressed as weight percentage.

[0144] <Oligomer Analysis> 5.6 μL of the sample oil / fat composition was dissolved in 1 mL of tetrahydrofuran (for GPC) and used as an analysis sample for gel filtration chromatography. On the chromatogram of the analysis results, those with a faster elution time than triacylglycerol (those with a larger molecular weight) were analyzed as oligomers. The oligomer content was determined by calculating the area of ​​each peak using Shimadzu Corporation's waveform processing algorithm "i-Peak Finder" and calculating the ratio of the oligomer peak area to the sum of the areas of each peak.

[0145] HPLC Conditions (Method for Measuring Oligomers in Fish Oil, Rich in Omega-3 Acids, EUROPEAN PHARMACOPOEIA 8.0) Column: Phenogel 5 μm, Length 300 mm x Inner Diameter 7.8 mm (Three columns with pore sizes of 500 Å, 100 Å, and 50 Å were connected in this order.) Mobile Phase: Tetrahydrofuran Flow Rate: 0.8 mL / min Detector: RI Injection Volume: 40 μL Column Temperature: 40°C <Analysis of Fatty Acid Composition> 20 μL of sample was transferred to an assist tube, and 1 mL of 1 mol / L sodium ethylate was added and stirred for 30 seconds. Then, 1 mL of 1 mol / L hydrochloric acid was added to stop the ethylation reaction. After adding 1 mL of hexane and 5 mL of saturated saline, the mixture was centrifuged and the hexane layer was collected and subjected to gas chromatography with a flame ionization detector (hereinafter also referred to as GC-FID) analysis under the following conditions: In the chart analyzing the fatty acid composition, the peaks of each component were identified, and the peak area of ​​each fatty acid was calculated using the Agilent ChemStation integration algorithm. The content of each peak component was calculated as the ratio of each peak area to the total peak area of ​​the fatty acids.

[0146] Analysis conditions Model: GC6890N (Agilent Technologies) Column: DB-WAX (column length: 30 m, inner diameter: 0.25 mm, film thickness: 0.25 μm) Detector: FID Injection amount: 1 μL Injection port temperature: 250° C. Detection port temperature: 250° C. Oven temperature: After holding at 180° C. for 10 minutes, increase the temperature to 230° C. at a rate of 3° C. per minute and hold for 15 minutes Split ratio: 30:1 Carrier gas: helium (flow rate: 1 mL / min) Furthermore, column fractionation in Example 3 was carried out by the method described below.

[0147] <Removal of ethyl esters by column fractionation> 36 g of silica gel suspended in hexane was poured into a glass column, which was then filled and equilibrated with 100 mL of hexane. 0.5 g of sample was weighed into a 100 mL Erlenmeyer flask, dissolved in approximately 1 mL of hexane, and applied to the column. 140 mL of hexane, 280 mL of a diethyl ether and hexane mixture A (diethyl ether:hexane = 1:99 (v / v)), and 280 mL of a diethyl ether and hexane mixture B (diethyl ether:hexane = 5:95 (v / v)) were applied to the column in this order to obtain the ethyl ester fraction. 300 mL of diethyl ether was applied to the column to obtain the post-column oil. The absence of ethyl ester bands in the post-column oil was confirmed by thin-layer chromatography as described below.

[0148] Thin-layer chromatography: 10 μL of sample was dissolved in 990 μL of hexane, and 1 μL of the solution was spotted onto a TLC glass plate (TLC Silica gel 60 F254, Merck). The plate was developed with hexane:diethyl ether:acetic acid = 90:10:1 and then dried. After drying, the plate was immersed in anisaldehyde and heated on a hot plate at 200 °C to check for color development.

[0149] <Method for preparing fatty acid ethyl esters> Sardine oil was subjected to ethyl esterification treatment using ethanol in a conventional manner to prepare fatty acid ethyl esters containing 17% EPA and 8% DHA. This fatty acid ethyl ester was used as a fatty acid composition in the reactions in the following examples and comparative examples.

[0150] Example 1: 2.3 g of glycerol was added to a mixture of 16 mL of ethanol and 309 μL of 25 w / v% aqueous sodium hydroxide solution and stirred at 40°C for 30 minutes under a nitrogen atmosphere to obtain a catalyst mixture. After cooling, 24 g of fatty acid ethyl ester (EPA 17%, DHA 8%; in-house production) was added to the catalyst mixture and stirred to obtain a dispersed emulsion of the reaction mixture. The reaction mixture was gradually depressurized with stirring at 40°C until the pressure inside the system reached 130 Pa, then heated to 120°C and stirred for 4.5 hours. Hydrochloric acid (1.5 equivalents relative to the alkali content of the reaction mixture) was added and stirred, followed by washing with an appropriate amount of saturated saline. After centrifugation, the pH of the aqueous layer was confirmed to be 3 or less, and the oil layer was washed again with water. Water washing was repeated until the pH of the aqueous layer reached 5-6. The mixture was then dehydrated at 40°C and 500 Pa for 20 minutes. The weight of the oil composition after dehydration was 19.4 g.

[0151] The resulting oil and fat composition was analyzed for TAG ratio and DAG ratio (AREA%) using TLC-FID and an Iatroscan MK-6 (Mitsubishi Iatron). No MAG was detected. The resulting oil and fat composition was also analyzed for oligomers. The results are shown in Table 1.

[0152] Example 2: 2.3 g of glycerol was added to a mixture of 16 mL of ethanol and 452 μL of 48 w / w% aqueous potassium hydroxide solution and stirred at 40°C for 30 minutes under a nitrogen atmosphere to obtain a catalyst mixture. After cooling, 24 g of fatty acid ethyl ester (EPA 17%, DHA 8%; in-house production) was added to the catalyst mixture and stirred, obtaining a dispersed emulsion of the reaction mixture. The reaction mixture was gradually depressurized while stirring at 40°C until the pressure inside the system reached 130 Pa, then heated to 75°C and stirred for 6.5 hours. Hydrochloric acid (1.5 equivalents relative to the alkali content of the reaction mixture) was added and stirred, followed by washing with an appropriate amount of saturated saline. After centrifugation, the pH of the aqueous layer was confirmed to be 3 or less, and the oil layer was washed again with water. Washing with water was repeated until the pH of the aqueous layer reached 5-6. The mixture was then dehydrated at 40°C and 500 Pa for 20 minutes. The weight of the oil composition after dehydration was 20.1 g.

[0153] The obtained oil and fat composition was analyzed for TAG ratio and DAG ratio (area %) using TLC-FID and Iatroscan MK-6 (Mitsubishi Iatron). No MAG was detected. Furthermore, the obtained sample was analyzed for oligomers. The results are shown in Table 1.

[0154] Comparative Example 1: A reaction was carried out using the same processing conditions as in Example 1 of CN103242969(B). Specifically, 24 g of fatty acid ethyl ester (EPA 17%, DHA 8%; in-house production), 2.3 g of glycerol, and 247.4 mg of sodium hydroxide were mixed and stirred. The mixture did not disperse, and the glycerol and sodium hydroxide precipitated to the bottom layer. The mixture was gradually depressurized while stirring at room temperature until the pressure inside the system reached 130 Pa. The temperature was then raised to 155-165°C, and the esterification reaction was carried out for 1 hour. The ethanol produced during the reaction was cooled and collected using a trap. After the reaction, the mixture was cooled to room temperature, and 48 mL of purified water was added to the reactor for water washing. After centrifugation, the oil layer was extracted. This water washing process was repeated three times. The reactor was then evacuated using an 8000 kPa water-sealed vacuum pump and heated to 75-80°C for dehydration. The sample weight after dehydration was 19.8 g.

[0155] The obtained samples were also analyzed for oligomers, and the results are shown in Table 1.

[0156] Comparative Example 2: 309 μL of 25 w / v% aqueous sodium hydroxide and 2.3 g of glycerol were mixed, and 24 g of fatty acid ethyl ester (EPA 17%, DHA 8%; in-house production) was added and stirred. The mixture did not disperse, and the aqueous sodium hydroxide and glycerol precipitated in the lower layer. The mixture was gradually reduced in pressure while stirring at 40°C. After the pressure in the system reached 130 Pa, the system was heated to 120°C. Sampling was performed at regular intervals. 1.5 equivalents of hydrochloric acid relative to the alkalinity of the mixture were added and stirred, followed by washing with an appropriate amount of saturated saline. After centrifugation, the pH of the aqueous layer was confirmed to be 3 or less, and the oil layer was washed again with water. Washing with water was repeated until the pH of the aqueous layer reached 5-6. The mixture was then dehydrated for 20 minutes at 40°C and 500 Pa. The sample weight after dehydration was 18.9 g.

[0157] The obtained sample was analyzed for TAG ratio and DAG ratio (AREA%) using TLC-FID, Iatroscan MK-6 (Mitsubishi Iatron). The results at reaction times of 4.5 hours and 6.5 hours are shown in Table 1.

[0158] Comparative Example 3: 452 μL of 48 w / w% potassium hydroxide solution and 2.3 g of glycerol were mixed, and 24 g of fatty acid ethyl ester (EPA 17%, DHA 8%; in-house production) was added and stirred. The mixture did not disperse, and the sodium hydroxide solution and glycerol precipitated in the lower layer. The mixture was gradually reduced in pressure while stirring at 40°C. After the pressure in the system reached 130 Pa, the system was heated to 75°C. Sampling was performed at regular intervals. 1.5 equivalents of hydrochloric acid relative to the alkali content of the mixture were added and stirred, followed by washing with an appropriate amount of saturated saline. After centrifugation, the pH of the aqueous layer was confirmed to be 3 or less, and the oil layer was washed again with water. Washing with water was repeated until the pH of the aqueous layer reached 5-6. The mixture was then dehydrated at 40°C and 500 Pa for 20 minutes. The sample weight after dehydration was 18.5 g.

[0159] The resulting sample was analyzed for the TAG ratio (AREA%) using a TLC-FID Iatroscan MK-6 (Mitsubishi Iatron). The results at reaction times of 6.5 hours and 10 hours are shown in Table 1.

[0160] The table below summarizes the test conditions and analysis results for each test.

[0161]

[0162] *MAG was not detected in any of Examples 1 and 2 and Comparative Examples 1, 2, and 3.

[0163] Example 3 <Weight ratio of constituent fatty acids to total constituent fatty acids and weight ratio at sn2 position> The oil and fat compositions prepared in Examples 1 and 2 and water-washed sardine oil (manufactured in-house) were each analyzed as samples.

[0164] Weight ratio of each constituent fatty acid to all constituent fatty acids The fatty acid composition of the sample was analyzed to obtain the weight ratio of the constituent fatty acids of the acylglycerol to all fatty acids.

[0165] Weight ratio of constituent fatty acids at the sn2 position After removing ethyl esters from the sample by column fractionation, the fatty acid composition was analyzed in accordance with Standard Method for Analysis of Fats and Oils 2.4.5-2016, "Fatty Acid Composition at Position 2 of Triacylglycerol (Enzymatic Interesterification Method)," to obtain the weight ratio of constituent fatty acids at the sn2 position of acylglycerol.

[0166] From these analytical results, the ratio of the weight ratio of each type of constituent fatty acid in the total constituent fatty acids to the weight ratio at the sn2 position was calculated.

[0167] Analysis results of the weight ratio of constituent fatty acids of acylglycerol to the total constituent fatty acids and the weight ratio at sn2 position

[0168]

Claims

1. A method for producing an oil composition comprising acylglycerol, the acylglycerol including triacylglycerol, comprising: １－６ In the presence of an alcohol and a catalyst, glycerol or C １－６ A fatty acid glycerol ester and a fatty acid or its C １－６ subjecting a fatty acid composition containing an alcohol ester to a reaction, and obtaining an oil and fat composition produced by the reaction.

2. The C is removed from the reaction mixture during the reaction. １－６ 10. The process of claim 1, further comprising removing the alcohol.

3. The glycerol or C １－６ a fatty acid glycerol ester, the catalyst, and the C １－６ 3. The process of claim 1 or 2, comprising: mixing an alcohol to obtain a catalyst mixture; and mixing the catalyst mixture and the fatty acid composition and subjecting the resulting reaction mixture to the reaction.

4. The method of claim 3, wherein combining the catalyst mixture and the fatty acid composition comprises adding the fatty acid composition to the catalyst mixture.

5. The process according to claim 4, wherein the catalyst mixture is mixed at 30°C to 50°C, and then the fatty acid composition is added.

6. The method according to any one of claims 1 to 5, wherein the catalyst is an alkaline catalyst.

7. The process according to any one of claims 1 to 6, wherein the reaction is carried out at 40°C to 160°C.

8. The method according to any one of claims 1 to 7, wherein the reaction is carried out at 3000 Pa or less.

9. The fatty acid composition and the C １－６ The process according to any one of claims 1 to 8, wherein the weight ratio of alcohol is from 2:1 to 1:

10.

10. The glycerol or C １－６ The C for fatty acid glycerol esters １－６ The method according to any one of claims 1 to 9, wherein the molar ratio of the alcohol is 1:10 or more and 1:100 or less.

11. The process according to any one of claims 1 to 10, wherein the catalyst is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium alcoholate, or potassium alcoholate.

12. The method according to any one of claims 1 to 11, wherein the reaction is carried out at 1000 Pa or less.

13. The method of any one of claims 1 to 12, wherein the fatty acid composition is derived from a marine oil or a microbial oil.

14. The fatty acid composition is a PUFA or its C １－６ The method according to any one of claims 1 to 13, wherein the alcohol ester is contained in an amount of 25% by weight or more.

15. Above C １－６ The process according to any one of claims 1 to 14, wherein the alcohol is ethanol.

16. The method according to any one of claims 1 to 15, wherein the fatty acid composition contains 25% by weight or more of EPA ethyl ester and DHA ethyl ester in total.

17. A method for producing an oil composition according to any one of claims 1 to 16, wherein, among the fatty acids which are constituent fatty acids of acylglycerol in the oil composition, there are three or more fatty acids which are present in a weight ratio of 5% by weight or more relative to the total constituent fatty acids, at least one of the fatty acids which is present in a weight ratio of 5% by weight or more is a PUFA, for all of the fatty acids which are present in a weight ratio of 5% by weight or more, the ratio of the weight ratio in the total constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

18. The method of claim 17, wherein the PUFA in the oil composition comprises an omega-3 highly unsaturated fatty acid.

19. The method of claim 17 or 18, wherein the PUFA in the oil composition comprises EPA or DHA.

20. A method for producing acylglycerol according to any one of claims 17 to 19, wherein, for all fatty acids present in an amount of 1% by weight or more of the total fatty acids, the weight ratio of each fatty acid in the total fatty acids to the sn2 position is 7:10 or more and 13:10 or less.

21. The method according to any one of claims 17 to 20, wherein the content of oligomers in the oil composition is 0.4 area % or less as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.

0.

22. The method according to any one of claims 17 to 21, wherein the oil composition contains triacylglycerol in an amount of 50% by weight or more.

23. The method of any one of claims 17 to 22, wherein the oil composition further contains 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

24. The method of claim 23, wherein the oil composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

25. A method for producing a food according to any one of claims 17 to 24, wherein the constituent fatty acids contain PUFAs in an amount of 25% by weight or more.

26. A method for producing according to any one of claims 17 to 25, wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

27. A method for producing an oil composition containing acylglycerol, the acylglycerol including triacylglycerol, comprising: １－６ A production method comprising: reacting glycerol with a fatty acid composition containing an ethyl ester of a fatty acid in the presence of an alcohol and a catalyst, and obtaining an oil and fat composition produced by the reaction.

28. The C is separated from the reaction mixture during the reaction. １－６ 28. The process of claim 27, further comprising removing the alcohol.

29. The glycerol, the catalyst, and the C １－６ 29. The process of claim 27 or 28, comprising: mixing an alcohol to obtain a catalyst mixture; and mixing the catalyst mixture and a fatty acid composition comprising an ethyl ester of the fatty acid, and subjecting the resulting mixture to the reaction.

30. The method of claim 29, wherein combining the catalyst mixture and the fatty acid composition comprises: adding the fatty acid composition to the catalyst mixture.

31. The process of claim 30, wherein the catalyst mixture is mixed at 30°C to 50°C and then the fatty acid composition is added.

32. The method according to any one of claims 27 to 31, wherein the catalyst is an alkaline catalyst.

33. The process according to any one of claims 27 to 32, wherein the reaction is carried out at 40°C to 160°C.

34. The method of any one of claims 27 to 33, wherein the reaction is carried out at 3000 Pa or less.

35. The fatty acid composition and the C １－６ The process according to any one of claims 27 to 34, wherein the weight ratio of alcohol is from 2:1 to 1:

10.

36. The C to glycerol １－６ The method according to any one of claims 27 to 35, wherein the molar ratio of alcohol is 1:10 or more and 1:100 or less.

37. The process according to any one of claims 27 to 36, wherein the catalyst is sodium hydroxide, potassium hydroxide, calcium hydroxide, a sodium alcoholate, or a potassium alcoholate.

38. The method of any one of claims 27 to 37, wherein the reaction is carried out at 1000 Pa or less.

39. The method of any one of claims 27 to 38, wherein the fatty acid composition is derived from a marine oil or a microbial oil.

40. A method according to any one of claims 27 to 39, wherein the fatty acid composition contains 25% by weight or more of ethyl esters of PUFA.

41. Said C １－６ The process according to any one of claims 27 to 40, wherein the alcohol is ethanol.

42. The method according to any one of claims 27 to 41, wherein the fatty acid composition contains 25% by weight or more of EPA ethyl ester and DHA ethyl ester in total.

43. The method of any one of claims 27 to 42, wherein the molar ratio of glycerol to ethyl ester of fatty acid is from 1:3 to 1:

9.

44. A method for producing an oil or fat composition according to any one of claims 27 to 43, wherein, among the fatty acids which are constituent fatty acids of acylglycerol in the oil or fat composition, there are three or more fatty acids which are present in a weight ratio of 5% by weight or more relative to the total constituent fatty acids, at least one of the fatty acids which is present in a weight ratio of 5% by weight or more is a PUFA, for all of the fatty acids which are present in a weight ratio of 5% by weight or more, the ratio of the weight ratio in the total constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil or fat composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

45. The method of production described in claim 44, wherein the PUFA in the oil composition includes omega-3 highly unsaturated fatty acids.

46. ​​The method of claim 44 or 45, wherein the PUFA in the oil composition comprises EPA or DHA.

47. A method for producing an acylglycerol according to any one of claims 44 to 46, in which, for all fatty acids present in an amount of 1% by weight or more relative to the total amount of fatty acids, the weight ratio of each fatty acid in the total amount of fatty acids to the sn2 position is 7:10 or more and 13:10 or less.

48. The method according to any one of claims 44 to 47, wherein the content of oligomers in the oil composition is 0.4 area % or less as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.

0.

49. The method of any one of claims 44 to 48, wherein the oil composition contains triacylglycerol in an amount of 50% by weight or more.

50. A method for producing a composition according to any one of claims 44 to 49, wherein the oil composition further contains 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

51. The method of claim 50, wherein the oil composition contains triacylglycerol and diacylglycerol in a total amount of 55% by weight or more.

52. A method for producing a food according to any one of claims 44 to 51, wherein the constituent fatty acids contain PUFAs in an amount of 25% by weight or more.

53. A method for production according to any one of claims 44 to 52, wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

54. An oil composition comprising an acylglycerol, the acylglycerol including a triacylglycerol, wherein among the fatty acids which are constituent fatty acids of the acylglycerol, there are three or more types of fatty acids present in a weight ratio of 5% by weight or more relative to all constituent fatty acids, at least one of the fatty acids present in a weight ratio of 5% by weight or more is a PUFA, for all of the fatty acids present in a weight ratio of 5% by weight or more, the ratio of the weight ratio in all constituent fatty acids to the weight ratio at the sn2 position of the acylglycerol is 5:10 or more and 17:10 or less, and the content of oligomers in the oil composition measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

55. The oil composition according to claim 54, wherein the PUFA comprises an omega-3 highly unsaturated fatty acid.

56. An oil composition according to claim 54 or 55, wherein the PUFA comprises EPA or DHA.

57. An oil or fat composition described in any one of claims 54 to 56, in which, for all fatty acids present in an amount of 1% by weight or more of the total constituent fatty acids among the constituent fatty acids of an acylglycerol, the weight ratio of each fatty acid to the total constituent fatty acids and the weight ratio of each fatty acid at the sn2 position is 7:10 or more and 13:10 or less.

58. The oil or fat composition according to any one of claims 54 to 57, wherein the content of oligomers in the oil or fat composition as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area % or less.

59. The oil composition according to any one of claims 54 to 58, wherein the oil composition contains triacylglycerol in an amount of 50% by weight or more.

60. The oil or fat composition according to any one of claims 54 to 59, further comprising 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

61. The oil or fat composition of claim 60, wherein the oil or fat composition comprises a total of 55% by weight or more of triacylglycerol and diacylglycerol.

62. An oil or fat composition described in any one of claims 54 to 61, wherein the constituent fatty acids contain PUFAs in a proportion of 25% by weight or more.

63. An oil or fat composition according to any one of claims 54 to 62, wherein the constituent fatty acids contain EPA and DHA in a total amount of 25% by weight or more.

64. An oil or fat composition produced by the method according to any one of claims 1 to 26.

65. An oil composition comprising an acylglycerol, the acylglycerol including a triacylglycerol, the triacylglycerol being a reconstituted triacylglycerol, and the content of oligomers in the oil composition as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.8 area % or less.

66. The oil or fat composition according to claim 65, wherein at least one of the constituent fatty acids of the acylglycerol is a PUFA.

67. The oil composition according to claim 66, wherein the PUFA comprises an omega-3 highly unsaturated fatty acid.

68. The oil composition of claim 66 or 67, wherein the PUFA comprises EPA or DHA.

69. The oil or fat composition according to any one of claims 65 to 68, wherein the content of oligomers in the oil or fat composition as measured based on the measurement method in EUROPEAN PHARMACOPOEIA 8.0 is 0.4 area % or less.

70. The oil composition according to any one of claims 65 to 69, wherein the oil composition contains triacylglycerol in an amount of 50% by weight or more.

71. The oil or fat composition according to any one of claims 65 to 70, further comprising 5% by weight or more, or 10% by weight or more, and / or 40% by weight or less of diacylglycerol.

72. The oil or fat composition of claim 71, wherein the oil or fat composition comprises a total of 55% by weight or more of triacylglycerol and diacylglycerol.

73. The oil and fat composition according to any one of claims 65 to 72, wherein the constituent fatty acids of the acylglycerol contain PUFA in a proportion of 25% by weight or more.

74. An oil or fat composition according to any one of claims 65 to 72, wherein the constituent fatty acids of the acylglycerol contain EPA and DHA in a total amount of 25% by weight or more.

75. An oil or fat composition produced by the method according to any one of claims 1 to 26.

76. Use of the oil or fat composition according to any one of claims 54 to 75 in the production of food, medicine, or quasi-drug.

77. A food, medicine, or quasi-drug comprising the oil or fat composition according to any one of claims 54 to 75.

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