WO2016101894A1 - Oil/fat composition and preparation method for the same - Google Patents

Oil/fat composition and preparation method for the same Download PDF

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Publication number
WO2016101894A1
WO2016101894A1 PCT/CN2015/098459 CN2015098459W WO2016101894A1 WO 2016101894 A1 WO2016101894 A1 WO 2016101894A1 CN 2015098459 W CN2015098459 W CN 2015098459W WO 2016101894 A1 WO2016101894 A1 WO 2016101894A1
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Prior art keywords
oil
fat
triglyceride
preparation
present
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PCT/CN2015/098459
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French (fr)
Inventor
Jianchun WAN
Kefeng NI
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Wilmar (Shanghai) Biotechnology Research & Development Center Co., Ltd.
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Publication of WO2016101894A1 publication Critical patent/WO2016101894A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A23D9/04—Working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol

Definitions

  • the present invention provides an oil/fat composition and a preparation method for the same.
  • Human milk is an optimal source of nutrition for infant and young child.
  • Human milk contains 3%-4.5%of fat.
  • the fat and the corresponding fatty acid provide 50-60%of energy to infant and young child, and essential fatty acids necessary for growth and development.
  • the fat can promote the absorption of the fat soluble vitamin in the body. It is believed that the fatty acid composition in the fat of human milk and the structure characteristics are the golden standard for the oil in the formula milk powder for infant and young child.
  • composition and the distribution of the fatty acids in human milk fat have the following characteristics: (1) the content of triacylglycerol (TAG) in the fat of human milk comprises 98%or more; (2) for the total fatty acid composition, the content of oleic acid that is the leading monounsaturated fatty acid is highest, and the content of palmitic acid that is the leading saturated fatty acid is 20-30%; (3) for the fatty acid distribution, the unsaturated fatty acid is mainly located at Sn-1, 3 of TAG, and more than 70%of palmitic acid is located at Sn-2 of TAG.
  • TAG triacylglycerol
  • the composition and the site distribution of the fat of human milk are closely relevant to the digestion and absorption of infant and young child. It is demonstrated that the fat is mainly hydrolyzed in the body of infant and young child by gastric lipase and pancreatic lipase that are specific to Sn-1, 3 to form free fatty acids and 2-monoglyceride. 2-monoglyceride is absorbed by lymphatic system and comes into the blood circulation. However, there exists a large difference for the human in the aspect of absorbing free fatty acids. On average, the effect of digestion and absorption by long-chain saturated fatty acids is inferior to those by middle or short chain saturated fatty acids and unsaturated fatty acids.
  • the long chain saturated fatty acid has a higher melting point than the body temperature, and is prone to form insoluble saponified substance in the small intestine, resulting in the double loss in energy and mineral substance.
  • free palmitic acid has a very low absorption in the small intestine, and the resulting saponified substance is also prone to cause the stool dryness, while the palmitic acid monoglyceride at Sn-2 is easily digested and absorbed in the small intestine.
  • WO1994268551 has disclosed that the palm oil and the palm kernel oil in a certain ratio are subjected to an directed interesterification in the catalysis of Sn-1, 3 specific lipase, and the interesterified product is blended with other vegetable oils in a certain ratio to produce an oil/fat composition having a ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid of 40%or more.
  • CN101940241 discloses a method for producing a HMFS, wherein an oil/fat of catfish from Mekong delta is used as starting material, the oil/fat is fractionated to give a liquid composition, the liquid composition and a mixed fatty acid or a mixed fatty acid lower alcohol are subjected to an enzymatic interesterification reaction to produce HMFS, in which the ratio of the palmitic acid at Sn-2 to the total palmitic acid is 60%or more.
  • WO2007029018A1 discloses a method for producing a 1, 3-dioleoyl-2-palmitoylglycerol (OPO) containing composition, in which a palm oil stearin having an iodine value of 8-12 and oleic acid or a non-glycerol ester thereof are subjected to an enzymatic directed interesterification.
  • OPO 1, 3-dioleoyl-2-palmitoylglycerol
  • CN102827885A discloses a composition containing 1, 3-di-unsaturated fatty acyl-2-saturated fatty acyl glyceride, a method for producing the same and a use thereof, wherein an ester rich in the saturated fatty acid residue and an ester rich in the unsaturated fatty acid residue are mixed and subjected to a random interesterification, the randomized oil/fat and an unsaturated fatty acid or an ester of the unsaturated fatty acid are subjected to an enzymatic interesterification.
  • the ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid is 45%or more.
  • the enzymatic directed interesteried reaction can increase the ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid in the oil/fat composition.
  • these techniques are restricted to the screening of the oil/fat starting material, the pretreating of the starting material, or the subsequent process such as fractionation.
  • An object of the present invention is to provide a preparation method for an oil/fat composition, wherein a triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase, wherein a polyol is present in the system.
  • said fatty acid is at least one of straight-chain or branched, saturated or non-saturated fatty acids containing 16-30 carbon atoms.
  • said preparation method for the oil/fat composition comprises: the step of a triglyceride and a fatty acid or a derivative thereof being subjected to a directed interesterification in the presence of a specific lipase, said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
  • said specific lipase is a Sn-1, 3 specific lipase.
  • the non-limiting example of said Sn-1, 3-specific lipase can be at least one of Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida rugosa lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase or porcine pancreatic lipase or lipase D.
  • said triglyceride contains a triglyceride represented by general formula (1) ,
  • R 1 , R 2 and R 3 are each identical or different, at least one of R 1 , R 2 and R 3 represents a group derived from straight-chain or branched, saturated fatty acids containing 8-30 carbon atoms.
  • said R 1 , R 2 and R 3 are each identical or different, at least one of R 1 , R 2 and R 3 represents a group derived from straight saturated fatty acids containing 16-18 carbon atoms.
  • said triglyceride is vegetable-derived.
  • said triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride, avegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
  • said triglyceride is at least one of palm oil stearin, palm oil, palm oil fractionation, randomly interesterified palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil fractionation.
  • said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
  • the catalyst used in said enzymatic random interesterification is a non-specific lipase.
  • the non-limiting example of said non-specific lipase can be Lipozyme TL IM.
  • said polyol is a 2-to 6-membered alcohol.
  • said polyol is at least one member selected from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolethane, erythritol, pentaerythritol, sorbitol and xylitol.
  • the amount of said polyol is 1-30wt%, preferably 5-20wt%, more preferably 5-10wt%.
  • said fatty acid is at least one member selected from the group consisting of straight-chain unsaturated fatty acids containing 16-20 carbon atoms
  • said fatty acid derivative is at least one member selected from the group consisting of esters of straight-chain unsaturated fatty acids containing 16-20 carbon atoms.
  • said fatty acid or a derivative thereof is preferably at least one of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower seed oil and high oleic palm oil.
  • the preparation method for the oil/fat composition according to the present invention is useful to prepare a human milk fat substitute and increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the human milk fat substitute, in particular increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in a HMFS.
  • the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the triglyceride composition can be increased, in particular the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute can be increased.
  • Another object of the present invention is to provide an oil/fat composition prepared with the preparation method for the oil/fat composition according to the present invention.
  • Another object of the present invention is to provide a preparation method for a human milk fat substitute, wherein a triglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase, wherein a polyol is present in the system.
  • said specific lipase is a Sn-1, 3-specific lipase.
  • the non-limiting example of said Sn-1, 3-specific lipase can be at least one of Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP43 5, lipase SP382, Candida rugosa lipase, lipase MC7, Novozym 435, Candida antarctic lipase B, R275A lipase, porcine pancreatic lipase and lipase D.
  • said triglyceride is vegetable-derived.
  • said triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride, a vegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
  • said triglyceride is at least one of palm oil stearin, palm oil, palm oil fractionation, randomly interesterified palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil fractionation.
  • said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
  • the catalyst used in said enzymatic random interesterification is a non-specific lipase.
  • the non-limiting example of said non-specific lipase can be Lipozyme TL IM.
  • said polyol is a 2-to 6-membered alcohol.
  • said polyol is at least one member selected from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolethane, erythritol, pentaerythritol, sorbitol and xylitol.
  • the amount of said polyol is 1-30wt%, preferably 5-20wt%, more preferably 5-10wt%.
  • said oleic acid or a derivative thereof is preferably at least one of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower seed oil and high oleic palm oil.
  • the preparation method for the oil/fat composition according to the present invention is useful to prepare a human milk fat substitute and increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the human milk fat substitute, in particular increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in a HMFS.
  • Another object of the present invention is to provide an oil/fat composition, which contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is at least 52%, preferably 52-70%, more preferably 54-68%, further preferably 59-65%.
  • the non-saturated fatty acid residue (s) at Sn-1 and Sn-3 positions is the oleic acid residue or the linoleic acid residue.
  • Sn-2 palmitic acid content is 30-60wt%, preferably 40-55wt%, more preferably 45-50wt%.
  • the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 20-45wt%, preferably 25-35wt%, more preferably 28-33wt%.
  • the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 50-80wt%, preferably 60-75wt%, more preferably 62-70wt%.
  • said oil/fat composition is a human milk fat substitute.
  • said oil/fat composition is 1, 3-dioleoyl 2-palmitoyl triglyceride.
  • Another object of the present invention is to provide a method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride, wherein the triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase, wherein a polyol is present in the system, preferably said fatty acid or a derivative thereof is at least one member selected from the group consisting of a straight-chain or branched, saturated or unsaturated fatty acid containing 16-30 carbon atoms or a derivative thereof, preferably at least one member selected from the group consisting of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower seed oil and high oleic palm oil.
  • Another object of the present invention is to provide a composition, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide a food, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide a formula milk powder for infant and young child, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide a formula food for infant and young child, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide a substitute for human milk fat composition, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide a dietary ingredient, which contains the oil/fat composition or the human milk fat substitute according to the present invention.
  • Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a formula milk powder for infant and young child.
  • Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a formula food for infant and young child.
  • Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a human milk fat substitute.
  • Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a dietary ingredient.
  • the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the product can be increased. Furthermore, the preparation method for the present invention can increase the nutrition value of the product.
  • the addition of a certain ratio of polyol can remarakably increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the composition, in particurly increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute composition.
  • the addition of polyol can increase the reation rate of the enzymatic directedinteresterification, and save the reaction time.
  • the method of the present invention can improve the interesterification for various starting materials and therefore have a good universality. Moreover, the method of the present invention can be easily operated. In addition, the added polyol is safe, nontoxic and inexpensive, and can increase the reaction rate.
  • Fig. 1 shows the content of oleic acid in the triglyceride at different time points in Example 1 and Comparative Example 1.
  • Atriglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase, wherein a polyol is present in the system.
  • said triglyceride and a fatty acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase
  • said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
  • said polyol is added to the reaction system before the interesterification.
  • said directed interesterification is a directed interesterification at Sn-1, 3 positions of the triglyceride.
  • said specific lipase is Sn-1, 3 specific lipase.
  • said Sn-1, 3 specific lipase can be at least one of Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida rugosa lipase, lipase MC7, Novozym 435, Candida antarctic lipase B, R275A lipase, porcine pancreatic lipase or lipase D (for example, lipase D produced by Amano Enzyme Manufacturing Ltd) .
  • said triglyceride contains a triglyceride represented by general formula (1) ,
  • R 1 , R 2 and R 3 are each identical or different, at least one of R 1 , R 2 and R 3 represents a group derived from straight-chain or branched, saturated fatty acids containing 8-30 carbon atoms.
  • R 1 , R 2 and R 3 are each identical or different, at least one of R 1 , R 2 and R 3 represents a group derived from straight saturated fatty acids containing 16-18 carbon atoms.
  • at least one of R 1 , R 2 and R 3 represents a group derived from palmitic acid.
  • R 1 , R 2 and R 3 are identical and represent a group derived from palmitic acid.
  • said triglyceride can be animal-derived or vegetable-derived, preferably vegetable-derived.
  • Said vegetable-derived triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride, a vegetable oil containing palmitoyl triglyceride, and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
  • said triglyceride is at least one member selected from the group consisting of palm oil stearin, palm oil, palm oil fractionation, randomly interesterified palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil fractionation.
  • said triglyceride is a refined oil/fat.
  • said triglyceride can also be obtained in the following way: a vegetable oil/fat is subjected to a conventional random interesterification in the presence of a catalyst to obtain a randomized oil/fat.
  • Said vegetable oil/fat is at least one member selected from the group consisting of rice oil, sunflower seed oil, colleseed oil, palm oil, palm kernel oil, peanut oil, rapeseed oil, soybean oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, olive oil, cocoa bean oil, Chinese tallowseed oil, almond oil, apricot kernel oil, tallowseed oil, rubber seed oil, maize oil, wheat germ oil, sesame seed oil, castor oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, borage seed oil, seabuckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil and the like, preferably palm oil.
  • said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
  • said random interesterification is a chemical random interesterification.
  • the chemical catalyst used in the chemical random interesterification is an acidic catalyst or an alkaline catalyst; preferably, said chemical catalyst is NaOH, KOH, NaOCH 3 , an organic base, a soild base catalyst, sulphuric acid, sulfonic acid or a solid acid catalyst; more preferably, said chemical catalyst is NaOH, KOH, NaOCH 3 , sulphuric acid or sulfonic acid.
  • the chemical interesterification can be conventionally performed, for example, the oil/fat starting materials are mixed, a catalyst is added in an amount of 0.01-3%by weight of the oil/fat starting materials, and then the resulting mixture is stirred under reduced pressure at a temperature of 80-160°Cfor 20-90 min. After the completion of the interesterification, the catalyst is deactivated with hot water (having a temperature higher than the melting point of the fat/oil) or an aqueous solution of citric acid or phosphoric acid to terminate the interesterification.
  • hot water having a temperature higher than the melting point of the fat/oil
  • an aqueous solution of citric acid or phosphoric acid to terminate the interesterification.
  • said random interesterification is an enzymatic random interesterification.
  • Said enzymatic interesterification comprises but is not limited to an interesterification, in which a lipase is used as catalyst.
  • Alipase powder or an immobilized lipase such as a lipase powder immobilized on a support such as diatomite or an ion-exchange resin can be used as lipase.
  • the lipase used in the random interesterification is for a site-specificity deficient interesterification, and includes but is not limited to: a lipase derived from Alcaligenes, a lipase derived from Candida and the like.
  • the enzymatic interesterification can for example be conducted in the following manner. To a fat/oil starting material is added 0.02-10wt%of a lipase powder or an immobilized lipase. Then the resulting mixture is stirred at 40-80°Cfor 0.5-48 hours. After the completion of the interesterification, the lipase powder or the immobilized lipase is removed by filtering and the like.
  • Said lipase is for example Lipozyme TL IM.
  • the resulting randomized oil/fat is used in the preparation method for the oil/fat composition according to the present invention, or the resulting randomized oil/fat is subjected to the following refinement step to obtain a refined oil/fat, which is further used in the preparation method for the oil/fat composition according to the present invention.
  • reaction mixture After the completion of the random interesterification, the reaction mixture can be conventionally subjected to washing, desoponificating, drying, decoloring and filtering to obtain a refined oil/fat.
  • the fatty acid of the present invention or a derivative thereof is preferably at least one of a straight-chain or branched, saturated or unsaturated fatty acid containing 16-30 carbon atoms or a derivative thereof.
  • the fatty acid according to the present invention is preferably at least one of straight-chain unsaturated fatty acids containing 16-20 carbon atoms, and its example can include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosapentaenoic acid and the like, preferably at least one of palmitoleic acid, oleic acid, linoleic acid, and linolenic acid.
  • the derivative of the fatty acid according to the present invention is preferably at least one of esters of a straight-chain unsaturated fatty acid containing 16-20 carbon atoms.
  • Said ester can be a C1-20 alkyl ester of the above fatty acid according to the present invention, a C2-20 alkenyl ester of the above fatty acid according to the present invention, a C6-20 aryl ester of the above fatty acid according to the present invention, a C7-20 aralkyl ester of the above fatty acid according to the present invention and the like.
  • said ester is a non-glyceryl ester.
  • alkyl ester can include methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester, hexyl ester, heptyl ester, octyl ester, nonyl ester, decyl ester, undecyl ester, dodecyl ester, hexadecyl ester, octadecyl ester and the like.
  • alkenyl ester can include ethenyl ester, propenyl ester, butenyl ester, pentenyl ester, hexenyl ester, heptenyl ester, octenyl ester, nonenyl ester, decenyl ester, undecylenyl ester, dodecenyl ester, hexadecylenyl ester, octadecenyl ester and the like.
  • An example of said aryl ester can include phenyl ester, nathphyl ester and the like.
  • An example of said aralkyl ester can include benzyl ester and the like. Methyl ester or ethyl ester is preferable.
  • the fatty acid of the present invention or a derivative thereof is preferably at least one member selected from the group consisting of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower seed oil and high oleic palm oil.
  • Said triglyceride and the fatty acid of the present invention or a derivative thereof are added in a ratio, by weight, of the triglyceride to the fatty acid of the present invention or a derivative thereof of 1 ⁇ 5, preferably 1 ⁇ 4, more preferably 1 ⁇ 3, further preferably 1 ⁇ 2, particularly preferably 1 ⁇ 1.5.
  • Said interesterification is preferably conducted under heating.
  • the heating temperature is not particularly limited as long it does not negatively influence the object of the present invention, for example 50-80°C, preferably 60°C.
  • the interesterification time is not particularly limited as long it does not negatively influence the object of the present invention, for example 0.5-20 hours, preferably 1-10 hours.
  • said polyol is a 2-to 6-membered alcohol, preferably at least one member selected from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolethane, erythritol, pentaerythritol, sorbitol and xylitol. More preferably, said polyol is at least one of propylene glycol, glycerol and erythritol.
  • the amount of said polyol is 1-30wt%, preferably 5-20wt%, more preferably 5-10wt%. Based on the total amount of the triglyceride and the fatty acid of the present invention or a derivative thereof, the amount of said polyol is for example 3wt%, 5wt%, 10wt%, 20wt%.
  • the preparation method for the oil/fat composition according to the present invention further comprises a step of separating the reaction product from the unreacted starting material after the interesterification.
  • the separation is not particularly limited, and its example can include the separation by filtration, the separation by centrifugation and the like.
  • palm oil stearin is subjected to a chemical interesterification.
  • the resulting randomized oil/fat and oleic acid are mixed in a ratio of 1 ⁇ 2 (weight ratio) , glycerol is added in an amount of 5%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • the step of the chemical interesterification is conducted by drying palm oil stearin in vacuum at 105°Cfor 1h and adding 0.2wt%of NaOCH 3 at 105°C.
  • An aqueous citric acid solution is added in an amount of 20%by weight of the reaction mixture to terminate the reaction.
  • the reaction mixture is subjected to washing, desoponificating, drying, decoloring and filtering to obtain a refined oil/fat.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 10%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 20%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and ethyl oleate are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in an amount of 5%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil is subjected to a randomization to obtain a randomized oil/fat, and the randomized oil/fat is refined to obtain a refined oil/fat.
  • the resulting refined oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 3%by the total weight of the refined oil/fat and oleic acid, and then a lipase is added in amount of 6%by the total weight of the refined oil/fat and oleic acid to conduct a directed interesterification.
  • the randomization of palm oil is conducted by reacting palm oil and a lipase (in an amount of 6%by weight of palm oil) at 65°Cfor 24hr to obtain a randomized oil/fat.
  • the randomized oil/fat was dried in vacuum at 105°Cfor 0.5hr.
  • the reaction mixture is subjected to washing, desoponificating, drying, decoloring and filteringto obtain a refined oil/fat.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a wei ght ratio of 1 ⁇ 2, 1, 2-propylene glycol is added in amount of 5%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total wei ght of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a wei ght ratio of 1 ⁇ 2, 1, 2-propylene glycol is added in amount of 10%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, erythritol is added in amount of 5%bv the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • a preparation method for the human milk fat substitute according to the present invention atriglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase, wherein a polyol is present in the system.
  • said triglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase
  • said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
  • said polyol is added to the reaction system before the interesterification.
  • said directed interesterification is a directed interesterification at 1-and 3-positions of triglyceride.
  • said specific lipase is a Sn-1, 3 specific lipase.
  • the non-limiting example of said Sn-1, 3 specific lipase can be Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida rugosa lipase, lipase MC7, Novozym 435, Candida antarctic lipase B, R275A lipase, porcine pancreatic lipase or lipase D (e.g., lipase D produced by Amano Enzyme Manufacturing Ltd) .
  • said triglyceride can be animal-derived or vegetable-derived, preferably vegetable-derived.
  • Said vegetable-derived triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride, a vegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
  • said triglyceride is at least one member selected from the group consisting of palm oil stearin, palm oil, palm oil fractionation, randomly interesterified palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil fractionation.
  • said triglyceride is a refined oil/fat.
  • said triglyceride can be also obtained in the following manner.
  • a vegetable fat/oil is subjected to a conventional random interesterification in the presence of a catalyst to obtain a randomized oil/fat.
  • Said vegetable oil/fat is at least one member selected from the group consisting of rice oil, sunflower seed oil, colleseed oil, palm oil, palm kernel oil, peanut oil, rapeseed oil, soybean oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, olive oil, cocoa bean oil, Chinese tallowseed oil, almond oil, apricot kernel oil, tallowseed oil, rubber seed oil, maize oil, wheat germ oil, sesame seed oil, castor oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, borage seed oil, seabuckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil and the like, preferably palm oil.
  • said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
  • said random interesterification is a chemical random interesterification
  • the chemical catalyst used in the chemical random interesterification is an acidic catalyst or an alkaline catalyst; preferably, said chemical catalyst is NaOH, KOH, NaOCH 3 , an organic base, a soild base catalyst, sulphuric acid, sulfonic acid or a solid acid catalyst; more preferably, said chemical catalyst is NaOH, KOH, NaOCH 3 , sulphuric acid or sulfonic acid.
  • the chemical interesterification can be conventionally performed, for example, the oil/fat starting materials are mixed, acatalyst is added in an amount of 0.01-3%by weight of the oil/fat starting materials, and then the resulting mixture is stirred under reduced pressure at a temperature of 80-160°Cfor 20-90 min.
  • the catalyst is deactivated with hot water (having a temperature higher than the melting point of the fat/oil) or an aqueous solution of citric acid or phosphoric acid to terminate the interesterification.
  • said random interesterification is an enzymatic random interesterification.
  • Said enzymatic interesterification comprises but is not limited to an interesterification, in which a lipase is used as catalyst.
  • Alipase powder or an immobilized lipase such as a lipase powder immobilized on a support such as diatomite or an ion-exchange resin can be used as lipase.
  • the lipase used in the random interesterification is for a non-specific interesterification, and includes but is not limited to: a lipase derived from Alcaligenes, a lipase derived from Candida and the like.
  • the enzymatic interesterification can for example be conducted in the following manner.
  • a fat/oil starting material is added 0.02-10wt%of a lipase powder or an immobilized lipase.
  • the resulting mixture is stirred at 40-80°Cfor 0.5-48 hours.
  • the lipase powder or the immobilized lipase is removed by filtering and the like.
  • Said lipase is for example Lipozyme TL IM.
  • the resulting randomized oil/fat is used in the preparation method for the oil/fat composition according to the present invention, or the resulting randomized oil/fat is subjected to the following refining step to obtain a refined oil/fat, which is further used in the preparation method for the oil/fat composition according to the present invention.
  • the reaction mixture can be conventionally subjected to washing, desoponificating, drying, decoloring and filtering to obtain a refined oil/fat.
  • the derivative of oleic acid according to the present invention can be an alkyl ester of oleic acid.
  • An example of said alkyl ester can include methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester, hexyl ester, heptyl ester, octyl ester, nonyl ester, decyl ester, undecyl ester, dodecyl ester, hexadecyl ester, octadecyl ester and the like.
  • alkenyl ester can include ethenyl ester, propenyl ester, butenyl ester, pentenyl ester, hexenyl ester, heptenyl ester, octenyl ester, nonenyl ester, decenyl ester, undecylenyl ester, dodecenyl ester, hexadecylenyl ester, octadecenyl ester and the like.
  • An example of said aryl ester can include phenyl ester, nathphyl ester and the like.
  • An example of said aralkyl ester can include benzyl ester and the like. Methyl ester or ethyl ester is preferable.
  • the derivative of oleic acid according to the present invention is preferably at least one member selected from the group consisting of ethyl oleate, methyl oleate, high oleic sunflower seed oil and high oleic palm oil.
  • Said triglyceride and oleic acid or a derivative thereof are added in a weight ratio of the triglyceride to oleic acid or a derivative thereof being 1 ⁇ 5, preferably 1 ⁇ 4, more preferably 1 ⁇ 3, further preferably 1 ⁇ 2, particularly preferably 1 ⁇ 1.5.
  • Said interesterification is preferably conducted under heating.
  • the heating temperature is not particularly limited as long it does not negatively influence the object of the present invention, for example 50-80°C, preferably 60°C.
  • the interesterification time is not particularly limited as long it does not negatively influence the object of the present invention, for example 0.5-20 hours, preferably 1-10 hours.
  • said polyol is a 2-to 6-membered alcohol, preferably at least one member selected from the group consisting of ethylene glycol, propylene glycol, glycerol, trimethylolethane, erythritol, pentaerythritol, sorbitol and xylitol. More preferably, said polyol is at least one of propylene glycol, glycerol and erythritol.
  • the amount of said polyol is 1-30wt%, preferably 5-20wt%, more preferably 5-10wt%. Based on the total amount of the triglyceride and oleic acid or a derivative thereof, the amount of said polyol is for example 3wt%, 5wt%, 1 0wt%, 20wt%.
  • the preparation method for the human milk fat substitute according to the present invention further comprises a step of separating the reaction product from the unreacted starting material after the interesterification.
  • the separation is not particularly limited, and its example can include the separation by filtration, the separation by centrifugation and the like.
  • palm oil stearin is subjected to a chemical interesterification.
  • the resulting randomized oil/fat and oleic acid are mixed in a ratio of 1 ⁇ 2 (weight ratio) , glycerol is added in an amount of 5%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • the step of the chemical interesterification is conducted by drying palm oil stearin in vacuum at 105°Cfor 1h and adding 0.2wt%of NaOCH3 at 105°C.
  • An aqueous citric acid solution is added in an amount of 20%by weight of the reaction mixture to terminate the reaction.
  • the reaction mixture is subjected to washing, desoponificating, drying, decoloring and filtering to obtain a refined oil/fat.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 10%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total wei ght of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 20%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total wei ght of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and ethyl oleate are mixed in a wei ght ratio of 1 ⁇ 2, glycerol is added in an amount of 5%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total wei ght of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil is subjected to a randomization to obtain a randomized oil/fat, and the randomized oil/fat is refined to obtain a refined oil/fat.
  • the resulting refined oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, glycerol is added in amount of 3%by the total weight of the refined oil/fat and oleic acid, and then a lipase i s added in amount of 6%by the total weight of the refined oil/fat and oleic acid to conduct a directed interesterification.
  • the randomization of palm oil is conducted by reacting palm oil and a lipase (in an amount of 6%by weight of palm oil) at 65°Cfor 24hr to obtain a randomized oil/fat.
  • the randomized oil/fat was dried in vacuum at 105°Cfor 0.5hr.
  • the reaction mixture is subjected to washing, desoponificating, drying, decoloring and filtering to obtain a refined oil/fat.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, 1, 2-propylene glycol is added in amount of 5%by the total weight of the randomized oil/fat and oleic acid, alipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, 1, 2-propylene glycol is added in amount of 1 0%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat.
  • the resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1 ⁇ 2, erythritol is added in amount of 5%by the total weight of the randomized oil/fat and oleic acid, a lipase is then added in an amount of 6%by the total weight of the randomized oil/fat and oleic acid, and the resulting mixture is subjected to a directed interesterification.
  • the oil/fat composition of the present invention contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is at least 52%, preferably 52-70%, more preferably 54-68%, further preferably 59-65%, for example, 59.3%, 59.5%, 61%, 63.3%, 63.4%.
  • the unsaturated fatty acid residue at Sn-1 and Sn-3 positions of said triglyceride is the oleic acid residue or the linoleic acid residue.
  • the Sn-2 palmitic acid content in said triglyceride mixture is 3 0-60wt%, preferably 40-55wt%, more preferably 45-50wt%.
  • the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 20-45wt%, preferably 25-35wt%, more preferably 28-33wt%.
  • the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 50-80wt%, preferably 60-75wt%, more preferably 62-70wt%.
  • said oil/fat composition is a human milk fat substitute. In a more preferable embodiment of the present invention, said oil/fat composition is 1, 3-dioleoyl 2-palmitoyl triglyceride.
  • the fatty acid composition (FAC (%) ) is measured according to AOCS Celb-89.
  • the content of the fatty acid at Sn-2 position is measured according to AOCS Ch3-91.
  • Sn-2 position palmitic acid/total palmitic acid (%) Sn-2 position palmitic acid content (%) / (3 ⁇ total palmitic acid content (%) ) ⁇ 100%.
  • the oil/fat composition of the present invention can be prepared according to the above preparation method for the oil/fat composition.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 61%, the Sn-2 palmitic acid content in said triglyceride mixture is 49.8wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 30.3wt%, and the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 68.1wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 63.4%, the Sn-2 palmitic acid content in said triglyceride mixture is 51.9wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.4wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.4wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 59.5%, the Sn-2 palmitic acid content in said triglyceride mixture is 59.1 wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 34.5wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 64.7wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 59.3%, the Sn-2 palmitic acid content in said triglyceride mixture is 50.3wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 31.3wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 68.1wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 63.3%, the Sn-2 palmitic acid content in said triglyceride mixture is 51.1 wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.1wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.8wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 62.8%, the Sn-2 palmitic acid content in said triglyceride mixture is 34.8wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 22.8wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 76.2wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 62.8%, the Sn-2 palmitic acid content in said triglyceride mixture is 47.7wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.5wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.1wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 65.6%, the Sn-2 palmitic acid content in said triglyceride mixture is 50.2wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 26.7wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 72.6wt%.
  • the composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 54.1%, the Sn-2 palmitic acid content in said triglyceride mixture is 58.4wt%, the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 39.7wt%, the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 59wt%.
  • the saturated fatty acid in the oil/fat composition of the present invention is mainly bound at the Sn-2 position of the triglyceride, and the ratio of the saturated fatty acid at Sn-2 position to the total saturated fatty acid is high. Meanwhile, the unsaturated fatty acid is mainly bound at the Sn-1/3 positions of the triglyceride.
  • the oil/fat composition of the present invention is very similar to the oil/fat in the human milk with respect to the triglyceride structure.
  • the use of the oil/fat composition of the present invention as the human milk fat substitute can have an advantage such as promoting the absorption of the fat in infant and young child and increasing the absorption of the mineral substances.
  • the triglyceride and the fatty acid of the present invention or a derivative thereof are contacted in the presence of a lipase, wherein a polyol is present in the system.
  • said triglyceride and the fatty acid of the present invention or a derivative thereof are subjected to a step of the interesterification in the presence of a lipase
  • said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
  • said polyol is added to the reaction system before the interesterification.
  • Said interesterification is a directed interesterification.
  • the triglyceride, the fatty acid of the present invention or a derivative thereof, the lipase, and the polyol are identical to those discussed above.
  • the method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride according to the present invention further comprises a step of separating the reaction product from the unreacted starting material after the interesterification.
  • the separation is not particularly limited, and its example can include the separation by filration, the separation by centrifugation and the like.
  • the present invention provides a food containing the oil/fat composition or the human milk fat substitute according to the present invention.
  • the food can be selected from the group consisting of infant formula milk powder and infant formula food, bakery products, including bread, particularly biscuit and leavened dessert, dairy product, including milk and milk drink, ice cream, cereals, sauces, spreads, including margarine, oils and fats, soy products, meat products, fried foods, confection, cube candy, candy and chocolate, fast food, drinks and shake mixed drinks, ready-to-drink products, pre-prepared foods for infant, young child and adult, including pre-prepared vegetable purees and/or pulp, condiment, oils and fats for cooking, and meat products.
  • the food of the present invention includes but is not limited to dairy product, fried and baked foods, meat product, sauce, drink and the like, e.g. milk, yogurt, ice cream, milkshake, cheese, milk powder, cream, sterilized milk, modified milk, fermented milk, condensed milk, milk powder, whey powder, whey protein powder, dry cheese, processed cheese, formula food for infant and young child such as formula milk powder for infant and young child; potato chips, fried dough twist; cake, bread, pancake, snowcake, puff pastry, moon cake, Shaobing, Pie, toast, omelet purole, baked pudding, custard, biscuit, waffle, egg tart, instant noodles, instant rice, pizza, butter tea, sachima, popped rice cracker, Niangao, Zongzi; meat products: ham, sausage, bacon, Char Siu, luncheon meat, jerky, preserved pork, salt-cured meat, Chinese bacon, Chinese sausage; salad dressing, crisp candy, milk candy, milk tea, coffee, tea drink.
  • the food of the present invention can be conventionally prepared by contacting the oil/fat composition or the human milk fat substitute and food-acceptable support.
  • said food-acceptable support comprises but is not limited to, for example, starch, cellulose, dextrin, milk fat,animal and vegetable oil/fat such as sesame oil, soybean oil, peanut oil, palm oil, olive oil, maize oil, rapeseed oil, lard and tallow, edible gum such as arabic gum, gelatin, carrageenan, xanthan gum, guar gum, and sodium alginate, phospholipids such as lecithin and cephaline, baking powder and the like.
  • starch cellulose, dextrin
  • milk fat animal and vegetable oil/fat
  • vegetable oil/fat such as sesame oil, soybean oil, peanut oil, palm oil, olive oil, maize oil, rapeseed oil, lard and tallow
  • edible gum such as arabic gum, gelatin, carrageenan, xanthan gum, guar gum, and sodium alginate
  • phospholipids such as lecithin and cephaline
  • infant formula food refers to milk-based infant formula food or soy-based infant formula food.
  • the milk-based infant formula food refers to a liquid or powdery product, which is made only through a physical approach from milk and milk protein products as the maining starting material with the addition of an appropriate amount of vitamins, mineral substances and/or other ingredients. It is suitable to be fed with normal infant, and can provide the energy and the nutrition content satifying the normal nutritional requirement of 0-6 month-old infant.
  • the soy-based infant formula food refers to a liquid or powdery product, which is made only through a physical approach from soy and soy protein products as the maining starting material with the addition of an appropriate amount of vitamins, mineral substances and/or other ingredients. It is suitable to be fed with normal infant, and can provide the energy and the nutrition content satifying the normal nutritional requirement of 0-6 month-old infant.
  • the term “formula food for elder infant and young child” refer to a liquid or powdery product, which is made only through a physical approach from milk and milk protein products and/or soy and soy protein productsas the maining starting material with the addition of an appropriate amount of vitamins, mineral substances and/or other ingredients. It is suitable to be fed with elder infant and young child, and can provide the nutrition content satifying the partial nuntritional requirement of normal elder infant (6-12-month old) and young child (12-36-month old) .
  • oil/fat composition or the human milk fat substitute according to the present invention is used in the infant formula food or in the formula food for elder infant and young child, it can be mixed with cow milk, sheep milk, milk powder, milk fat and the like for use according to the formula design requirement.
  • infant and young child also refers to infant or elder infant and young child
  • formula food for infant and young child also refers to the infant formula food or the formula food for elder infant and young child.
  • the oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a formula milk powder for infant and young child.
  • the oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a formula food for infant and young child.
  • the oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a human milk fat substitute.
  • the oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a dietary ingredient.
  • the oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a food.
  • the fatty acid composition (FAC (%) ) in the product was measured according to AOCS Ce1b-89.
  • the content of the fatty acid at Sn-2 position in the product was measured according to AOCS Ch3-91.
  • the starting materials and the catalysts were commercially available.
  • the resulting mixture was kept at 110°Cfor 30min to conduct the decolorizaion, and filtered to obtain a decolored oil/fat.
  • the oil/fat was heated to 240°C, and deodorized at 2mbar in a purge of nitrogen for 2h to obtain a refined oil/fat 1.
  • Step 2 of Example 1 no glycerol was added in the mixture of the refined oil/fat and oleic acid, and other conditions were identical to those in Example 1. Samples were respectively taken at the reaction time of 1h, 2h, 3h, 5h, 7h, and 10h for measuring the content of oleic acid in the triglyceride. The result was shown in Fig. 1.
  • Step 2 of Example 1 the enzyme was removed by filtering after the reaction time of 5h to obtain an oil/fat composition I, and other conditions were identical to those in Example 1.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
  • Example 2 the amount of glycerol that was added to a mixture of the refined oil/fat and oleic acid was increased from 5%to 10%by the total weight of the mixture, and other conditions were identical to those in Example 2.
  • An oil/fat composition II was finally obtained.
  • Example 2 the amount of glycerol that was added to a mixture of the refined oil/fat and oleic acid was increased from 5%to 20%by the total weight of the mixture, and other conditions were identical to those in Example 2.
  • An oil/fat composition III was finally obtained.
  • Example 2 the lipase Lipozyme RM IM was replaced with lipase D (Amano Enzyme Manufacturing Ltd) , and other conditions were identical to those in Example 2.
  • An oil/fat composition IV was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
  • Example 2 oleic acid was replaced with ethyl oleate, and other conditions were identical to those in Example 2.
  • An oil/fat composition V was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
  • Example 2 no glycerol was added to the mixture of the refined oil/fat and oleic acid, and other conditions were identical to those in Example 2. An oil/fat composition VI was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
  • Sn-2 position palmitic acid/total palmitic acid (%) Sn-2 position palmitic acid content (%) / (3 ⁇ total palmitic acid content (%) ) ⁇ 100%
  • step 2 of Example 3 no glycerol was added in the mixture of the refined oil/fat and oleic acid, and other conditions were identical to those in Example 3. An oil/fat composition VIII was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 2.
  • Sn-2 position palmitic acid/total palmitic acid (%) Sn-2 position palmitic acid content (%) / (3 ⁇ total palmitic acid content (%) ) ⁇ 100%
  • Step 2 of Example 1 2-propylene glycol was added to the mixture of the refined oil/fat and oleic acid in an amount of 5%by the total weight of the mixture, and other conditions were identical to those in Example 1.
  • An oil/fat composition IX was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 3.
  • Step 2 of Example 1 2-propylene glycol was added to the mixture of the refined oil/fat and oleic acid in an amount of 10%by the total weight of the mixture, and other conditions were identical to those in Example 1.
  • An oil/fat composition X was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 3.
  • Sn-2 position palmitic acid/total palmitic acid (%) Sn-2 position palmitic acid content (%) / (3 ⁇ total palmitic acid content (%) ) ⁇ 100%
  • Step 2 of Example 1 erythritol was added to the mixture of the refined oil/fat and oleic acid in an amount of 5%by the total weight of the mixture, and other conditions were identical to those in Example 1.
  • An oil/fat composition XI was finally obtained.
  • the FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 4.
  • Sn-2 position palmitic acid/total palmitic acid (%) Sn-2 position palmitic acid content (%) / (3 ⁇ total palmitic acid content (%) ) ⁇ 100%
  • the addition of polyol in the enzymatic interesterification can effectively increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the product, in particular the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute.
  • the method of the present invention may be adaptable for the enzymatic interesterification with different starting materials.
  • the saturated fatty acids were mainly bound at Sn-2 position of the triglyceride, for example, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue was at least 52%, preferably 52-70%, more preferably 54-68%, further preferably 59-65%.
  • the unsaturated fatty acid residues at Sn-1 and Sn-3 positions of the triglyceride were the oleic acid residue or the linoleic acid residue.
  • the oil/fat composition of the present invention is very similar to the oil/fat in the human milk with respect to the triglyceride structure. Therefore, the use of the oil/fat composition of the present invention as the human milk fat substitute can have an advantage such as promoting the absorption of the fat in infant and young child and increasing the absorption of the mineral substances.

Abstract

An oil/fat composition and a preparation method for such oil/fat composition. In the preparation method for the oil/fat composition, a triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase, wherein a polyol is present in the system. The oil/fat composition contains a vegetable-derived triglyceride mixture, wherein in said triglyceride mixture, the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is at least 52%, and the unsaturated fatty acid residue at Sn-1 and Sn-3 positions is the oleic acid residue or the linoleic acid residue. The operation of the present preparation method is simple. The added polyol is safe, non-toxic and low-cost, and can increase the reaction rate. The oil/fat composition is useful for preparing of a formula milk powder for infant and young child, a formula food for infant and young child, and a substitute for human milk fat composition or a dietary ingredient.

Description

Oil/fat composition and preparation method for the same Technical Field
The present invention provides an oil/fat composition and a preparation method for the same.
Background
Human milk is an optimal source of nutrition for infant and young child. Human milk contains 3％-4.5％of fat. The fat and the corresponding fatty acid provide 50-60％of energy to infant and young child， and essential fatty acids necessary for growth and development. Meanwhile， as a carrier for fat soluble vitamin， the fat can promote the absorption of the fat soluble vitamin in the body. It is believed that the fatty acid composition in the fat of human milk and the structure characteristics are the golden standard for the oil in the formula milk powder for infant and young child. The composition and the distribution of the fatty acids in human milk fat have the following characteristics： (1) the content of triacylglycerol (TAG) in the fat of human milk comprises 98％or more； (2) for the total fatty acid composition， the content of oleic acid that is the leading monounsaturated fatty acid is highest， and the content of palmitic acid that is the leading saturated fatty acid is 20-30％； (3) for the fatty acid distribution， the unsaturated fatty acid is mainly located at Sn-1， 3 of TAG， and more than 70％of palmitic acid is located at Sn-2 of TAG.
The composition and the site distribution of the fat of human milk are closely relevant to the digestion and absorption of infant and young child. It is demonstrated that the fat is mainly hydrolyzed in the body of infant and young child by gastric lipase and pancreatic lipase that are specific to Sn-1， 3 to form free fatty acids and 2-monoglyceride. 2-monoglyceride is absorbed by lymphatic system and comes into the blood circulation. However， there exists a large difference for the human in the aspect of absorbing free fatty acids. On average， the effect of digestion and absorption by long-chain saturated fatty acids is inferior to those by  middle or short chain saturated fatty acids and unsaturated fatty acids. It is because the long chain saturated fatty acid has a higher melting point than the body temperature， and is prone to form insoluble saponified substance in the small intestine， resulting in the double loss in energy and mineral substance. Particularly for palmitic acid， free palmitic acid has a very low absorption in the small intestine， and the resulting saponified substance is also prone to cause the stool dryness， while the palmitic acid monoglyceride at Sn-2 is easily digested and absorbed in the small intestine.
Aiming at the characteristics of infant and young child for absorbing and digesting the fat， the provision of the fat/oil that is similar in the composition and the site distribution of the fatty acid to the fat of human milk is benefit to the growth and development of infant and young child. A common vegetable oil or a composition thereof is difficult to be close to the standard for the fat of human milk in the site distribution of the fatty acid. With the development of the biological technology， in particular， the enzyme engineering technology， the directed modification of the fatty acid distribution of the fat/oil with Sn-1， 3 specific lipase to produce human milk fat substitute (HMFS) has become a hot spot in the research. Currently， the preparation of HMF S with the above technology has been disclosed in the relevant patent applications. WO1994268551 has disclosed that the palm oil and the palm kernel oil in a certain ratio are subjected to an directed interesterification in the catalysis of Sn-1， 3 specific lipase， and the interesterified product is blended with other vegetable oils in a certain ratio to produce an oil/fat composition having a ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid of 40％or more.
CN101940241 discloses a method for producing a HMFS， wherein an oil/fat of catfish from Mekong delta is used as starting material， the oil/fat is fractionated to give a liquid composition， the liquid composition and a mixed fatty acid or a mixed fatty acid lower alcohol are subjected to an enzymatic interesterification reaction to produce HMFS， in which the ratio  of the palmitic acid at Sn-2 to the total palmitic acid is 60％or more.
WO2007029018A1 discloses a method for producing a 1， 3-dioleoyl-2-palmitoylglycerol (OPO) containing composition， in which a palm oil stearin having an iodine value of 8-12 and oleic acid or a non-glycerol ester thereof are subjected to an enzymatic directed interesterification. In the obtained OPO composition， the ratio of the palmitic acid at Sn-2 to the total palmitic acid is 50％or more. The method requires the involvement of the fractionation process， resulting in the increased process cost.
WO2006114791 discloses a HMFS， wherein the ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid is lower than 43.5％.
CN102827885A discloses a composition containing 1， 3-di-unsaturated fatty acyl-2-saturated fatty acyl glyceride， a method for producing the same and a use thereof， wherein an ester rich in the saturated fatty acid residue and an ester rich in the unsaturated fatty acid residue are mixed and subjected to a random interesterification， the randomized oil/fat and an unsaturated fatty acid or an ester of the unsaturated fatty acid are subjected to an enzymatic interesterification. In the obtained oil/fat composition， the ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid is 45％or more.
According to the above prior techniques， with purposedly selecting the starting material and using the lipase， the enzymatic directed interesteried reaction can increase the ratio of the saturated fatty acid at Sn-2 to the total saturated fatty acid in the oil/fat composition. However， these techniques are restricted to the screening of the oil/fat starting material， the pretreating of the starting material， or the subsequent process such as fractionation.
It still demands to further increase the ratio of the palmitic acid at Sn-2 to the total palmitic acid in oil/fat composition， so that it has a fatty acid distribution closer to the fat of human milk.
Summary of the Invention
An object of the present invention is to provide a preparation method for an oil/fat composition， wherein a triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase， wherein a polyol is present in the system.
According to the preparation method for the oil/fat composition according to the present invention， said fatty acid is at least one of straight-chain or branched， saturated or non-saturated fatty acids containing 16-30 carbon atoms.
According to the preparation method for the oil/fat composition according to the present invention， wherein said method comprises： the step of a triglyceride and a fatty acid or a derivative thereof being subjected to a directed interesterification in the presence of a specific lipase， said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
According to the preparation method for the oil/fat composition according to the present invention， said specific lipase is a Sn-1， 3 specific lipase. The non-limiting example of said Sn-1， 3-specific lipase can be at least one of Lipozyme RM IM， Lipozyme IM60， Lipozyme IM20， lipase SP435， lipase SP382， Candida rugosa lipase， lipase MC7， Novozym 435， Candida antarctica lipase B， R275A lipase or porcine pancreatic lipase or lipase D.
According to the preparation method for the oil/fat composition according to the present invention， said triglyceride contains a triglyceride represented by general formula (1) ，
Figure PCTCN2015098459-appb-000001
in said general formula (1) ， R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight-chain or branched， saturated fatty acids containing 8-30 carbon atoms.
According to the preparation method for the oil/fat composition according to the present invention， said R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight saturated fatty acids containing 16-18 carbon atoms.
According to the preparation method for the oil/fat composition according to the present invention， said triglyceride is vegetable-derived.
According to the preparation method for the oil/fat composition according to the present invention， said triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride， avegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
According to the preparation method for the oil/fat composition according to the present invention， said triglyceride is at least one of palm oil stearin， palm oil， palm oil fractionation， randomly interesterified palm oil stearin， randomly interesterified palm oil， and randomly interesterified palm oil fractionation.
According to the preparation method for the oil/fat composition according to the present invention， said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
In a specific embodiment according to the present invention， the catalyst used in said enzymatic random interesterification is a non-specific lipase. The non-limiting example of said non-specific lipase can be Lipozyme TL IM.
According to the preparation method for the oil/fat composition according to the present invention， said polyol is a 2-to 6-membered alcohol.
According to the preparation method for the oil/fat composition according to the present invention， said polyol is at least one member selected from the group consisting of ethylene glycol， propylene glycol， glycerol， trimethylolethane， erythritol， pentaerythritol， sorbitol and xylitol. 
According to the preparation method for the oil/fat composition according to the present invention， based on the total amount of said triglyceride and the fatty acid or a derivative thereof， the amount of said polyol is 1-30wt％， preferably 5-20wt％， more preferably 5-10wt％.
According to the preparation method for the oil/fat composition according to the present invention， said fatty acid is at least one member selected from the group consisting of straight-chain unsaturated fatty acids containing 16-20 carbon atoms， said fatty acid derivative is at least one member selected from the group consisting of esters of straight-chain unsaturated fatty acids containing 16-20 carbon atoms.
In a specific embodiment according to the present invention， said fatty acid or a derivative thereof is preferably at least one of oleic acid， ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
The preparation method for the oil/fat composition according to the present invention is useful to prepare a human milk fat substitute and increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the human milk fat substitute， in particular increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in a HMFS.
By adding the polyol， the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the triglyceride composition can be increased， in particular the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute can be increased.
Another object of the present invention is to provide an oil/fat composition prepared with the preparation method for the oil/fat composition according to the present invention.
Another object of the present invention is to provide a preparation method for a human milk fat substitute， wherein a triglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase， wherein a polyol is present in the system.
In the preparation method for human milk fat substitute according to  the present invention， said specific lipase is a Sn-1， 3-specific lipase. The non-limiting example of said Sn-1， 3-specific lipase can be at least one of Lipozyme RM IM， Lipozyme IM60， Lipozyme IM20， lipase SP43 5， lipase SP382， Candida rugosa lipase， lipase MC7， Novozym 435， Candida antarctic lipase B， R275A lipase， porcine pancreatic lipase and lipase D.
In the preparation method for human milk fat substitute according to the present invention， said triglyceride is vegetable-derived.
In the preparation method for human milk fat substitute according to the present invention， said triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride， a vegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
In the preparation method for human milk fat substitute according to the present invention， said triglyceride is at least one of palm oil stearin， palm oil， palm oil fractionation， randomly interesterified palm oil stearin， randomly interesterified palm oil， and randomly interesterified palm oil fractionation.
In the preparation method for human milk fat substitute according to the present invention， said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
In a specific embodiment according to the present invention， the catalyst used in said enzymatic random interesterification is a non-specific lipase. The non-limiting example of said non-specific lipase can be Lipozyme TL IM.
In the preparation method for human milk fat substitute according to the present invention， said polyol is a 2-to 6-membered alcohol.
In the preparation method for the human milk fat substitute according to the present invention， said polyol is at least one member selected from the group consisting of ethylene glycol， propylene glycol， glycerol， trimethylolethane， erythritol， pentaerythritol， sorbitol and xylitol.
In the preparation method for human milk fat substitute according to  the present invention， based on the total amount of said triglyceride and the fatty acid or a derivative thereof， the amount of said polyol is 1-30wt％， preferably 5-20wt％， more preferably 5-10wt％.
In the preparation method for human milk fat substitute according to the present invention， said oleic acid or a derivative thereof is preferably at least one of oleic acid， ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
The preparation method for the oil/fat composition according to the present invention is useful to prepare a human milk fat substitute and increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the human milk fat substitute， in particular increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in a HMFS.
Another object of the present invention is to provide an oil/fat composition， which contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is at least 52％， preferably 52-70％， more preferably 54-68％， further preferably 59-65％.
In a preferable embodiment of the present invention， in said oil/fat composition， the non-saturated fatty acid residue (s) at Sn-1 and Sn-3 positions is the oleic acid residue or the linoleic acid residue.
According to the oil/fat composition of the present invention， in said triglyceride mixture， Sn-2 palmitic acid content is 30-60wt％， preferably 40-55wt％， more preferably 45-50wt％.
According to the oil/fat composition of the present invention， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 20-45wt％， preferably 25-35wt％， more preferably 28-33wt％.
According to the oil/fat composition of the present invention， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 50-80wt％， preferably 60-75wt％， more preferably 62-70wt％.
In a preferable embodiment of the present invention， said oil/fat composition is a human milk fat substitute. In a preferable embodiment of the present invention， said oil/fat composition is 1， 3-dioleoyl 2-palmitoyl triglyceride.
Another object of the present invention is to provide a method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride， wherein the triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase， wherein a polyol is present in the system， preferably said fatty acid or a derivative thereof is at least one member selected from the group consisting of a straight-chain or branched， saturated or unsaturated fatty acid containing 16-30 carbon atoms or a derivative thereof， preferably at least one member selected from the group consisting of oleic acid， ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
Another object of the present invention is to provide a composition， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide a food， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide a formula milk powder for infant and young child， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide a formula food for infant and young child， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide a substitute for human milk fat composition， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide a dietary ingredient， which contains the oil/fat composition or the human milk fat substitute according to the present invention.
Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a formula milk powder for infant and young child.
Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a formula food for infant and young child.
Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a human milk fat substitute.
Another object of the present invention is to provide the use of the oil/fat composition or the human milk fat substitute according to the present invention in manufacture of a dietary ingredient.
Effect of the Invention
For the oil/fat composition prepared with the oil/fat preparation method for the present invention， the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the product can be increased. Furthermore， the preparation method for the present invention can increase the nutrition value of the product.
In the oil/fat preparation method for the present invention， the addition of a certain ratio of polyol can remarakably increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the composition， in particurly increase the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute composition.
The addition of polyol can increase the reation rate of the enzymatic directedinteresterification， and save the reaction time.
By modifying the enzymatic interesterification and increasing the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the product， the method of the present invention can improve the interesterification for various starting materials and therefore have a good  universality. Moreover， the method of the present invention can be easily operated. In addition， the added polyol is safe， nontoxic and inexpensive， and can increase the reaction rate.
Description of the Drawings
Fig. 1 shows the content of oleic acid in the triglyceride at different time points in Example 1 and Comparative Example 1.
Detailed Description
Preparation method for the oil/fat composition
In the preparation method for the oil/fat composition of the present invention， atriglyceride and a fatty acid or a derivative thereof (hereinafter sometimes referred to as ″the fatty acid of the present invention or a derivative thereof″ ) are contacted in the presence of a lipase， wherein a polyol is present in the system. In a preferred embodiment of the preparation method according to the present invention， said triglyceride and a fatty acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase， said polyol is optionally added to the reaction system before the interesterification or during the interesterification. Preferably， said polyol is added to the reaction system before the interesterification.
In a preferable embodiment of the present invention， said directed interesterification is a directed interesterification at Sn-1， 3 positions of the triglyceride. In a preferable embodiment of the present invention， said specific lipase is Sn-1， 3 specific lipase. As the non-limiting example， said Sn-1， 3 specific lipase can be at least one of Lipozyme RM IM， Lipozyme IM60， Lipozyme IM20， lipase SP435， lipase SP382， Candida rugosa lipase， lipase MC7， Novozym 435， Candida antarctic lipase B， R275A lipase， porcine pancreatic lipase or lipase D (for example， lipase D produced by Amano Enzyme Manufacturing Ltd) .
In a preferred embodiment of the preparation method according to the present invention， said triglyceride contains a triglyceride represented by  general formula (1) ，
Figure PCTCN2015098459-appb-000002
in said general formula (1) ， R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight-chain or branched， saturated fatty acids containing 8-30 carbon atoms. Preferably， R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight saturated fatty acids containing 16-18 carbon atoms. Further preferably， at least one of R1， R2 and R3 represents a group derived from palmitic acid. In an embodiment of the present invention， R1， R2 and R3 are identical and represent a group derived from palmitic acid.
In a preferred embodiment of the preparation method according to the present invention， said triglyceride can be animal-derived or vegetable-derived， preferably vegetable-derived. Said vegetable-derived triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride， a vegetable oil containing palmitoyl triglyceride， and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
In a preferable embodiment of the present invention， said triglyceride is at least one member selected from the group consisting of palm oil stearin， palm oil， palm oil fractionation， randomly interesterified palm oil stearin， randomly interesterified palm oil， and randomly interesterified palm oil fractionation.
In an embodiment of the present invention， said triglyceride is a refined oil/fat.
According to the present invention， said triglyceride can also be obtained in the following way： a vegetable oil/fat is subjected to a conventional random interesterification in the presence of a catalyst to  obtain a randomized oil/fat. Said vegetable oil/fat is at least one member selected from the group consisting of rice oil， sunflower seed oil， colleseed oil， palm oil， palm kernel oil， peanut oil， rapeseed oil， soybean oil， cottonseed oil， safflower seed oil， perilla seed oil， tea seed oil， olive oil， cocoa bean oil， Chinese tallowseed oil， almond oil， apricot kernel oil， tallowseed oil， rubber seed oil， maize oil， wheat germ oil， sesame seed oil， castor oil， evening primrose seed oil， hazelnut oil， pumpkin seed oil， walnut oil， grape seed oil， borage seed oil， seabuckthorn seed oil， tomato seed oil， macadamia nut oil， coconut oil， cocoa butter， algae oil and the like， preferably palm oil.
According to the present invention， said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
In a preferable embodiment of the present invention， said random interesterification is a chemical random interesterification. The chemical catalyst used in the chemical random interesterification is an acidic catalyst or an alkaline catalyst； preferably， said chemical catalyst is NaOH， KOH， NaOCH3， an organic base， a soild base catalyst， sulphuric acid， sulfonic acid or a solid acid catalyst； more preferably， said chemical catalyst is NaOH， KOH， NaOCH3， sulphuric acid or sulfonic acid.
In an embodiment of the present invention， the chemical interesterification can be conventionally performed， for example， the oil/fat starting materials are mixed， a catalyst is added in an amount of 0.01-3％by weight of the oil/fat starting materials， and then the resulting mixture is stirred under reduced pressure at a temperature of 80-160℃for 20-90 min. After the completion of the interesterification， the catalyst is deactivated with hot water (having a temperature higher than the melting point of the fat/oil) or an aqueous solution of citric acid or phosphoric acid to terminate the interesterification.
In an embodiment of the present invention， said random interesterification is an enzymatic random interesterification. Said enzymatic interesterification comprises but is not limited to an  interesterification， in which a lipase is used as catalyst. Alipase powder or an immobilized lipase such as a lipase powder immobilized on a support such as diatomite or an ion-exchange resin can be used as lipase. The lipase used in the random interesterification is for a site-specificity deficient interesterification， and includes but is not limited to： a lipase derived from Alcaligenes， a lipase derived from Candida and the like.
In an embodiment of the present invention， the enzymatic interesterification can for example be conducted in the following manner. To a fat/oil starting material is added 0.02-10wt％of a lipase powder or an immobilized lipase. Then the resulting mixture is stirred at 40-80℃for 0.5-48 hours. After the completion of the interesterification， the lipase powder or the immobilized lipase is removed by filtering and the like.
Said lipase is for example Lipozyme TL IM. The resulting randomized oil/fat is used in the preparation method for the oil/fat composition according to the present invention， or the resulting randomized oil/fat is subjected to the following refinement step to obtain a refined oil/fat， which is further used in the preparation method for the oil/fat composition according to the present invention.
After the completion of the random interesterification， the reaction mixture can be conventionally subjected to washing， desoponificating， drying， decoloring and filtering to obtain a refined oil/fat.
In a preferred embodiment of the preparation method according to the pre sent invention， the fatty acid of the present invention or a derivative thereof is preferably at least one of a straight-chain or branched， saturated or unsaturated fatty acid containing 16-30 carbon atoms or a derivative thereof. The fatty acid according to the present invention is preferably at least one of straight-chain unsaturated fatty acids containing 16-20 carbon atoms， and its example can include palmitoleic acid， oleic acid， linoleic acid， linolenic acid， eicosatrienoic acid， stearidonic acid， arachidonic acid， eicosapentaenoic acid and the like， preferably at least one of palmitoleic acid， oleic acid， linoleic acid， and linolenic acid.
The derivative of the fatty acid according to the present invention is  preferably at least one of esters of a straight-chain unsaturated fatty acid containing 16-20 carbon atoms. Said ester can be a C1-20 alkyl ester of the above fatty acid according to the present invention， a C2-20 alkenyl ester of the above fatty acid according to the present invention， a C6-20 aryl ester of the above fatty acid according to the present invention， a C7-20 aralkyl ester of the above fatty acid according to the present invention and the like.
In an embodiment of the present invention， said ester is a non-glyceryl ester.
An example of said alkyl ester can include methyl ester， ethyl ester， propyl ester， butyl ester， pentyl ester， hexyl ester， heptyl ester， octyl ester， nonyl ester， decyl ester， undecyl ester， dodecyl ester， hexadecyl ester， octadecyl ester and the like. An example of said alkenyl ester can include ethenyl ester， propenyl ester， butenyl ester， pentenyl ester， hexenyl ester， heptenyl ester， octenyl ester， nonenyl ester， decenyl ester， undecylenyl ester， dodecenyl ester， hexadecylenyl ester， octadecenyl ester and the like. An example of said aryl ester can include phenyl ester， nathphyl ester and the like. An example of said aralkyl ester can include benzyl ester and the like. Methyl ester or ethyl ester is preferable.
In a preferable embodiment of the present invention， the fatty acid of the present invention or a derivative thereof is preferably at least one member selected from the group consisting of oleic acid， ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
Said triglyceride and the fatty acid of the present invention or a derivative thereof are added in a ratio， by weight， of the triglyceride to the fatty acid of the present invention or a derivative thereof of 1∶5， preferably 1∶4， more preferably 1∶3， further preferably 1∶2， particularly preferably 1∶1.5.
Said interesterification is preferably conducted under heating. The heating temperature is not particularly limited as long it does not negatively influence the object of the present invention， for example 50-80℃， preferably 60℃.
The interesterification time is not particularly limited as long it does not negatively influence the object of the present invention， for example 0.5-20 hours， preferably 1-10 hours.
In a preferable embodiment of the preparation method for the oil/fat composition according to the present invention， said polyol is a 2-to 6-membered alcohol， preferably at least one member selected from the group consisting of ethylene glycol， propylene glycol， glycerol， trimethylolethane， erythritol， pentaerythritol， sorbitol and xylitol. More preferably， said polyol is at least one of propylene glycol， glycerol and erythritol.
In a preferable embodiment of the preparation method for the oil/fat composition according to the present invention， based on the total amount of the triglyceride and the fatty acid of the present invention or a derivative thereof， the amount of said polyol is 1-30wt％， preferably 5-20wt％， more preferably 5-10wt％. Based on the total amount of the triglyceride and the fatty acid of the present invention or a derivative thereof， the amount of said polyol is for example 3wt％， 5wt％， 10wt％， 20wt％.
In a preferable embodiment of the preparation method for the oil/fat composition according to the present invention， it further comprises a step of separating the reaction product from the unreacted starting material after the interesterification. The separation is not particularly limited， and its example can include the separation by filtration， the separation by centrifugation and the like.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification. The resulting randomized oil/fat and oleic acid are mixed in a ratio of 1∶2 (weight ratio) ， glycerol is added in an amount of 5％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification. The step of the chemical interesterification is  conducted by drying palm oil stearin in vacuum at 105℃for 1h and adding 0.2wt％of NaOCH3 at 105℃. An aqueous citric acid solution is added in an amount of 20％by weight of the reaction mixture to terminate the reaction. The reaction mixture is subjected to washing， desoponificating， drying， decoloring and filtering to obtain a refined oil/fat.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 10％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 20％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and ethyl oleate are mixed in a weight ratio of 1∶2， glycerol is added in an amount of 5％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil is subjected to a  randomization to obtain a randomized oil/fat， and the randomized oil/fat is refined to obtain a refined oil/fat. The resulting refined oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 3％by the total weight of the refined oil/fat and oleic acid， and then a lipase is added in amount of 6％by the total weight of the refined oil/fat and oleic acid to conduct a directed interesterification. The randomization of palm oil is conducted by reacting palm oil and a lipase (in an amount of 6％by weight of palm oil) at 65℃for 24hr to obtain a randomized oil/fat. The randomized oil/fat was dried in vacuum at 105℃for 0.5hr. The reaction mixture is subjected to washing， desoponificating， drying， decoloring and filteringto obtain a refined oil/fat.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a wei ght ratio of 1∶2， 1， 2-propylene glycol is added in amount of 5％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total wei ght of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a wei ght ratio of 1∶2， 1， 2-propylene glycol is added in amount of 10％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In a specific embodiment of the oil/fat composition preparation method according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， erythritol is added in amount of 5％bv the total weight of the randomized  oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
Preparation method for the human milk fat substitute
In a preparation method for the human milk fat substitute according to the present invention， atriglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase， wherein a polyol is present in the system. In a preferred embodiment of the preparation method according to the present invention， said triglyceride and oleic acid or a derivative thereof are subjected to a directed interesterification in the presence of a specific lipase， said polyol is optionally added to the reaction system before the interesterification or during the interesterification. Preferably， said polyol is added to the reaction system before the interesterification.
In a preferable embodiment of the present invention， said directed interesterification is a directed interesterification at 1-and 3-positions of triglyceride. In a preferable embodiment of the present invention， said specific lipase is a Sn-1， 3 specific lipase. The non-limiting example of said Sn-1， 3 specific lipase can be Lipozyme RM IM， Lipozyme IM60， Lipozyme IM20， lipase SP435， lipase SP382， Candida rugosa lipase， lipase MC7， Novozym 435， Candida antarctic lipase B， R275A lipase， porcine pancreatic lipase or lipase D (e.g.， lipase D produced by Amano Enzyme Manufacturing Ltd) .
In a preferable embodiment of the preparation method for the human milk fat substitute according to the present invention， said triglyceride can be animal-derived or vegetable-derived， preferably vegetable-derived. Said vegetable-derived triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride， a vegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
In a preferable embodiment of the present invention， said triglyceride  is at least one member selected from the group consisting of palm oil stearin， palm oil， palm oil fractionation， randomly interesterified palm oil stearin， randomly interesterified palm oil， and randomly interesterified palm oil fractionation. In a preferable embodiment of the present invention， said triglyceride is a refined oil/fat.
According to the present invention， said triglyceride can be also obtained in the following manner. A vegetable fat/oil is subjected to a conventional random interesterification in the presence of a catalyst to obtain a randomized oil/fat. Said vegetable oil/fat is at least one member selected from the group consisting of rice oil， sunflower seed oil， colleseed oil， palm oil， palm kernel oil， peanut oil， rapeseed oil， soybean oil， cottonseed oil， safflower seed oil， perilla seed oil， tea seed oil， olive oil， cocoa bean oil， Chinese tallowseed oil， almond oil， apricot kernel oil， tallowseed oil， rubber seed oil， maize oil， wheat germ oil， sesame seed oil， castor oil， evening primrose seed oil， hazelnut oil， pumpkin seed oil， walnut oil， grape seed oil， borage seed oil， seabuckthorn seed oil， tomato seed oil， macadamia nut oil， coconut oil， cocoa butter， algae oil and the like， preferably palm oil.
According to the present invention， said random interesterification is a chemical random interesterification or an enzymatic random interesterification.
In a preferable embodiment of the present invention， said random interesterification is a chemical random interesterification， the chemical catalyst used in the chemical random interesterification is an acidic catalyst or an alkaline catalyst； preferably， said chemical catalyst is NaOH， KOH， NaOCH3， an organic base， a soild base catalyst， sulphuric acid， sulfonic acid or a solid acid catalyst； more preferably， said chemical catalyst is NaOH， KOH， NaOCH3， sulphuric acid or sulfonic acid.
In a preferable embodiment of the present invention， the chemical interesterification can be conventionally performed， for example， the oil/fat starting materials are mixed， acatalyst is added in an amount of 0.01-3％by weight of the oil/fat starting materials， and then the resulting  mixture is stirred under reduced pressure at a temperature of 80-160℃for 20-90 min. After the completion of the interesterification， the catalyst is deactivated with hot water (having a temperature higher than the melting point of the fat/oil) or an aqueous solution of citric acid or phosphoric acid to terminate the interesterification.
In a preferable embodiment of the present invention， said random interesterification is an enzymatic random interesterification. Said enzymatic interesterification comprises but is not limited to an interesterification， in which a lipase is used as catalyst. Alipase powder or an immobilized lipase such as a lipase powder immobilized on a support such as diatomite or an ion-exchange resin can be used as lipase. The lipase used in the random interesterification is for a non-specific interesterification， and includes but is not limited to： a lipase derived from Alcaligenes， a lipase derived from Candida and the like.
In a preferable embodiment of the present invention， the enzymatic interesterification can for example be conducted in the following manner. To a fat/oil starting material is added 0.02-10wt％of a lipase powder or an immobilized lipase. Then the resulting mixture is stirred at 40-80℃for 0.5-48 hours. After the completion of the interesterification， the lipase powder or the immobilized lipase is removed by filtering and the like.
Said lipase is for example Lipozyme TL IM. The resulting randomized oil/fat is used in the preparation method for the oil/fat composition according to the present invention， or the resulting randomized oil/fat is subjected to the following refining step to obtain a refined oil/fat， which is further used in the preparation method for the oil/fat composition according to the present invention. After the completion of the random interesterification， the reaction mixture can be conventionally subjected to washing， desoponificating， drying， decoloring and filtering to obtain a refined oil/fat.
The derivative of oleic acid according to the present invention can be an alkyl ester of oleic acid. An example of said alkyl ester can include methyl ester， ethyl ester， propyl ester， butyl ester， pentyl ester， hexyl ester，  heptyl ester， octyl ester， nonyl ester， decyl ester， undecyl ester， dodecyl ester， hexadecyl ester， octadecyl ester and the like. An example of said alkenyl ester can include ethenyl ester， propenyl ester， butenyl ester， pentenyl ester， hexenyl ester， heptenyl ester， octenyl ester， nonenyl ester， decenyl ester， undecylenyl ester， dodecenyl ester， hexadecylenyl ester， octadecenyl ester and the like. An example of said aryl ester can include phenyl ester， nathphyl ester and the like. An example of said aralkyl ester can include benzyl ester and the like. Methyl ester or ethyl ester is preferable.
In a preferable embodiment of the present invention， the derivative of oleic acid according to the present invention is preferably at least one member selected from the group consisting of ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
Said triglyceride and oleic acid or a derivative thereof are added in a weight ratio of the triglyceride to oleic acid or a derivative thereof being 1∶5， preferably 1∶4， more preferably 1∶3， further preferably 1∶2， particularly preferably 1∶1.5.
Said interesterification is preferably conducted under heating. The heating temperature is not particularly limited as long it does not negatively influence the object of the present invention， for example 50-80℃， preferably 60℃.
The interesterification time is not particularly limited as long it does not negatively influence the object of the present invention， for example 0.5-20 hours， preferably 1-10 hours.
In a preferable embodiment of the preparation method for the human milk fat substitute according to the present invention， said polyol is a 2-to 6-membered alcohol， preferably at least one member selected from the group consisting of ethylene glycol， propylene glycol， glycerol， trimethylolethane， erythritol， pentaerythritol， sorbitol and xylitol. More preferably， said polyol is at least one of propylene glycol， glycerol and erythritol.
In a preferable embodiment of the preparation method for the human  milk fat substitute according to the present invention， based on the total amount of the triglyceride and oleic acid or a derivative thereof， the amount of said polyol is 1-30wt％， preferably 5-20wt％， more preferably 5-10wt％. Based on the total amount of the triglyceride and oleic acid or a derivative thereof， the amount of said polyol is for example 3wt％， 5wt％， 1 0wt％， 20wt％.
In a preferable embodiment of the preparation method for the human milk fat substitute according to the present invention， it further comprises a step of separating the reaction product from the unreacted starting material after the interesterification. The separation is not particularly limited， and its example can include the separation by filtration， the separation by centrifugation and the like.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification. The resulting randomized oil/fat and oleic acid are mixed in a ratio of 1∶2 (weight ratio) ， glycerol is added in an amount of 5％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification. The step of the chemical interesterification is conducted by drying palm oil stearin in vacuum at 105℃for 1h and adding 0.2wt％of NaOCH3 at 105℃. An aqueous citric acid solution is added in an amount of 20％by weight of the reaction mixture to terminate the reaction. The reaction mixture is subiected to washing， desoponificating， drying， decoloring and filtering to obtain a refined oil/fat.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 10％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of  6％by the total wei ght of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 20％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of 6％by the total wei ght of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and ethyl oleate are mixed in a wei ght ratio of 1∶2， glycerol is added in an amount of 5％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of 6％by the total wei ght of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil is subjected to a randomization to obtain a randomized oil/fat， and the randomized oil/fat is refined to obtain a refined oil/fat. The resulting refined oil/fat and oleic acid are mixed in a weight ratio of 1∶2， glycerol is added in amount of 3％by the total weight of the refined oil/fat and oleic acid， and then a lipase i s added in amount of 6％by the total weight of the refined oil/fat and oleic acid to conduct a directed interesterification. The randomization of palm oil is conducted by reacting palm oil and a lipase (in an amount of 6％by weight of palm oil) at 65℃for 24hr to obtain a randomized oil/fat. The randomized oil/fat was dried in vacuum at 105℃for 0.5hr. The reaction mixture is subjected to washing， desoponificating， drying， decoloring and filtering to obtain a refined oil/fat.
In an embodiment of the preparation method for the human milk fat  substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， 1， 2-propylene glycol is added in amount of 5％by the total weight of the randomized oil/fat and oleic acid， alipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， 1， 2-propylene glycol is added in amount of 1 0％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
In an embodiment of the preparation method for the human milk fat substitute according to the present invention， palm oil stearin is subjected to a chemical interesterification to obtain a randomized oil/fat. The resulting randomized oil/fat and oleic acid are mixed in a weight ratio of 1∶2， erythritol is added in amount of 5％by the total weight of the randomized oil/fat and oleic acid， a lipase is then added in an amount of 6％by the total weight of the randomized oil/fat and oleic acid， and the resulting mixture is subjected to a directed interesterification.
Oil/fat composition
The oil/fat composition of the present invention contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is at least 52％， preferably 52-70％， more preferably 54-68％， further preferably 59-65％， for example， 59.3％， 59.5％， 61％， 63.3％， 63.4％. The unsaturated fatty acid residue at Sn-1 and Sn-3 positions of said triglyceride is the oleic acid residue or the linoleic acid residue.
In a preferable embodiment of the present invention， the Sn-2 palmitic acid content in said triglyceride mixture is 3 0-60wt％， preferably 40-55wt％， more preferably 45-50wt％.
In a preferable embodiment of the present invention， in the oil/fat composition， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 20-45wt％， preferably 25-35wt％， more preferably 28-33wt％.
In a preferable embodiment of the present invention， in the oil/fat composition， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 50-80wt％， preferably 60-75wt％， more preferably 62-70wt％.
In a preferable embodiment of the present invention， said oil/fat composition is a human milk fat substitute. In a more preferable embodiment of the present invention， said oil/fat composition is 1， 3-dioleoyl 2-palmitoyl triglyceride.
According to the present invention， the fatty acid composition (FAC (％) ) is measured according to AOCS Celb-89. According to the present invention， the content of the fatty acid at Sn-2 position is measured according to AOCS Ch3-91. Sn-2 position palmitic acid/total palmitic acid (％) ＝Sn-2 position palmitic acid content (％) / (3×total palmitic acid content (％) ) ×100％.
The oil/fat composition of the present invention can be prepared according to the above preparation method for the oil/fat composition.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 61％， the Sn-2 palmitic acid content in said triglyceride mixture is 49.8wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 30.3wt％， and the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 68.1wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 63.4％， the Sn-2 palmitic acid content in said triglyceride mixture is 51.9wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.4wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.4wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 59.5％， the Sn-2 palmitic acid content in said triglyceride mixture is 59.1 wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 34.5wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 64.7wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 59.3％， the Sn-2 palmitic acid content in said triglyceride mixture is 50.3wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 31.3wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 68.1wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 63.3％， the Sn-2 palmitic acid content in said triglyceride mixture is 51.1 wt％， the  content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.1wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.8wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 62.8％， the Sn-2 palmitic acid content in said triglyceride mixture is 34.8wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 22.8wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 76.2wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 62.8％， the Sn-2 palmitic acid content in said triglyceride mixture is 47.7wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 28.5wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 70.1wt％.
In an embodiment of the oil/fat composition according to the present invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 65.6％， the Sn-2 palmitic acid content in said triglyceride mixture is 50.2wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 26.7wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 72.6wt％.
In an embodiment of the oil/fat composition according to the present  invention， the composition contains a vegetable-derived triglyceride mixture， wherein in said triglyceride mixture， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue is 54.1％， the Sn-2 palmitic acid content in said triglyceride mixture is 58.4wt％， the content of the saturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 39.7wt％， the content of the unsaturated fatty acids in the whole of fatty acids constituting the oil/fat composition is 59wt％.
The saturated fatty acid in the oil/fat composition of the present invention is mainly bound at the Sn-2 position of the triglyceride， and the ratio of the saturated fatty acid at Sn-2 position to the total saturated fatty acid is high. Meanwhile， the unsaturated fatty acid is mainly bound at the Sn-1/3 positions of the triglyceride. The oil/fat composition of the present invention is very similar to the oil/fat in the human milk with respect to the triglyceride structure. The use of the oil/fat composition of the present invention as the human milk fat substitute can have an advantage such as promoting the absorption of the fat in infant and young child and increasing the absorption of the mineral substances.
Method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride
In a method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride according to the present invention， the triglyceride and the fatty acid of the present invention or a derivative thereof are contacted in the presence of a lipase， wherein a polyol is present in the system.
In a preferable embodiment of the method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride according to the present invention， said triglyceride and the fatty acid of the present invention or a derivative thereof are subjected to a step of the interesterification in the presence of a lipase， said polyol is optionally added to the reaction system before the interesterification or during the interesterification. Preferably， said polyol is added to the reaction system  before the interesterification.
Said interesterification is a directed interesterification.
In the method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride according to the present invention， the triglyceride， the fatty acid of the present invention or a derivative thereof， the lipase， and the polyol are identical to those discussed above.
In a preferable embodiment of the method for changing the fatty acid (s) at Sn-1 position and/or Sn-3 position in a triglyceride according to the present invention， it further comprises a step of separating the reaction product from the unreacted starting material after the interesterification. The separation is not particularly limited， and its example can include the separation by filration， the separation by centrifugation and the like.
The present invention provides a food containing the oil/fat composition or the human milk fat substitute according to the present invention. The food can be selected from the group consisting of infant formula milk powder and infant formula food， bakery products， including bread， particularly biscuit and leavened dessert， dairy product， including milk and milk drink， ice cream， cereals， sauces， spreads， including margarine， oils and fats， soy products， meat products， fried foods， confection， cube candy， candy and chocolate， fast food， drinks and shake mixed drinks， ready-to-drink products， pre-prepared foods for infant， young child and adult， including pre-prepared vegetable purees and/or pulp， condiment， oils and fats for cooking， and meat products.
The food of the present invention includes but is not limited to dairy product， fried and baked foods， meat product， sauce， drink and the like， e.g. milk， yogurt， ice cream， milkshake， cheese， milk powder， cream， sterilized milk， modified milk， fermented milk， condensed milk， milk powder， whey powder， whey protein powder， dry cheese， processed cheese， formula food for infant and young child such as formula milk powder for infant and young child； potato chips， fried dough twist； cake， bread， pancake， snowcake， puff pastry， moon cake， Shaobing， Pie， toast， omelet profiterole， baked pudding， custard， biscuit， waffle， egg tart， instant noodles， instant  rice， pizza， butter tea， sachima， popped rice cracker， Niangao， Zongzi； meat products： ham， sausage， bacon， Char Siu， luncheon meat， jerky， preserved pork， salt-cured meat， Chinese bacon， Chinese sausage； salad dressing， crisp candy， milk candy， milk tea， coffee， tea drink. The formula food for infant and young child is preferable. In an embodiment of the present invention， the formula milk powder for infant and young child is preferable.
The food of the present invention can be conventionally prepared by contacting the oil/fat composition or the human milk fat substitute and food-acceptable support.
According to the present invention， said food-acceptable support comprises but is not limited to， for example， starch， cellulose， dextrin， milk fat，animal and vegetable oil/fat such as sesame oil， soybean oil， peanut oil， palm oil， olive oil， maize oil， rapeseed oil， lard and tallow， edible gum such as arabic gum， gelatin， carrageenan， xanthan gum， guar gum， and sodium alginate， phospholipids such as lecithin and cephaline， baking powder and the like.
According to the present invention， the term “infant formula food” refers to milk-based infant formula food or soy-based infant formula food.
The milk-based infant formula food refers to a liquid or powdery product， which is made only through a physical approach from milk and milk protein products as the maining starting material with the addition of an appropriate amount of vitamins， mineral substances and/or other ingredients. It is suitable to be fed with normal infant， and can provide the energy and the nutrition content satifying the normal nutritional requirement of 0-6 month-old infant.
The soy-based infant formula food refers to a liquid or powdery product， which is made only through a physical approach from soy and soy protein products as the maining starting material with the addition of an appropriate amount of vitamins， mineral substances and/or other ingredients. It is suitable to be fed with normal infant， and can provide the energy and the nutrition content satifying the normal nutritional  requirement of 0-6 month-old infant.
According to the present invention， the term “formula food for elder infant and young child” refer to a liquid or powdery product， which is made only through a physical approach from milk and milk protein products and/or soy and soy protein productsas the maining starting material with the addition of an appropriate amount of vitamins， mineral substances and/or other ingredients. It is suitable to be fed with elder infant and young child， and can provide the nutrition content satifying the partial nuntritional requirement of normal elder infant (6-12-month old) and young child (12-36-month old) .
In case that the oil/fat composition or the human milk fat substitute according to the present invention is used in the infant formula food or in the formula food for elder infant and young child， it can be mixed with cow milk， sheep milk， milk powder， milk fat and the like for use according to the formula design requirement.
According to the present invention， “infant and young child” also refers to infant or elder infant and young child， and the “formula food for infant and young child” also refers to the infant formula food or the formula food for elder infant and young child.
Use
The oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a formula milk powder for infant and young child.
The oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a formula food for infant and young child.
The oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a human milk fat substitute.
The oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a dietary ingredient.
The oil/fat composition or the human milk fat substitute according to the present invention can be used to prepare a food.
Hereinafter， each aspect of the present invention will be described in details in conjunction with the following examples， which are provided with an intention that those skilled in the art can better understand the present invention， but not for limiting the scope of the present invention.
The apparatuses and devices that are conventional in the art are used in the following examples. For the experiment method， for which the specific conditions are not listed out in the following examples， the method is conducted conventionally or under the manufacturer′s recommended conditions. Various starting materials used in the following examples， unless otherwise stated， are the conventional commercially available products. In the present description， including the following examples， unless otherwise specified， both “％” and “part (s) ” represent the welght percent.
Example
In the examples of the present invention， the fatty acid composition (FAC (％) ) in the product was measured according to AOCS Ce1b-89.
In the examples of the present invention， the content of the fatty acid at Sn-2 position in the product was measured according to AOCS Ch3-91.
In the examples of the present invention， the starting materials and the catalysts were commercially available.
Example 1
Step 1
500g palm oil stearin was warmed to 105℃， and stirred in vacuum for 1h to conduct the drying. 0.2％sodium methoxide was added， and the resulting mixture was reacted at 105℃for 45min. An aqueous citric acid solution (having a concentration of 8％) was added in an amount of 20％by weight of the above mixture， and the resulting mixture was stirred for 20min to terminate the reaction. The reaction mixture was repeatedly washed with hot water until pH＝7. The above mixture was heated to 105℃， and stirred in vacuum for 30min to conduct the drying. Activated clay was added in an amount of 2％by weight of the above dried mixture.  The resulting mixture was kept at 110℃for 30min to conduct the decolorizaion， and filtered to obtain a decolored oil/fat. The oil/fat was heated to 240℃， and deodorized at 2mbar in a purge of nitrogen for 2h to obtain a refined oil/fat 1.
Step 2
100g of the refined oil/fat 1 and oleic acid were mixed in a weight ratio of 1∶2. Glycerol was added in an amount of 5％by the total weight of the refined oil/fat 1 and oleic acid， and a lipase Lipozyme RM IM (Novozymes Company) was added in an amount of 6％by the total weight of the refined oil/fat 1 and oleic acid. The resulting mixture was subjected to a directed interesterification. The reaction temperature was 60℃. Samples were respectively taken at the reaction time of 1h， 2h， 3h， 5h， 7h， and 10h for measuring the content of oleic acid in the triglyceride. The result was shown in Fig. 1.
Comparative Example 1
In Step 2 of Example 1， no glycerol was added in the mixture of the refined oil/fat and oleic acid， and other conditions were identical to those in Example 1. Samples were respectively taken at the reaction time of 1h， 2h， 3h， 5h， 7h， and 10h for measuring the content of oleic acid in the triglyceride. The result was shown in Fig. 1.
It could be seen from Fig. 1 that， as the enzymatic interesterification went on， the original fatty acids at the 1， 3-positions of the triglyceride were progressively substituted with oleic acid， and therefore the content of oleic acid in the triglyceride product was progressively increased. During 0 to 3 hours， the content of oleic acid and the time were in a linear relationship， and the slope of the curve could reflect the rate of the enzymatic reaction. It was clear that the addition of glycerol to the reaction system could increase the initial rate of the enzymatic reaction.
Example 2
In Step 2 of Example 1， the enzyme was removed by filtering after the reaction time of 5h to obtain an oil/fat composition I， and other conditions were identical to those in Example 1. The FAC of the triglyceride product  and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Example 3
In Example 2， the amount of glycerol that was added to a mixture of the refined oil/fat and oleic acid was increased from 5％to 10％by the total weight of the mixture， and other conditions were identical to those in Example 2. An oil/fat composition II was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Example 4
In Example 2， the amount of glycerol that was added to a mixture of the refined oil/fat and oleic acid was increased from 5％to 20％by the total weight of the mixture， and other conditions were identical to those in Example 2. An oil/fat composition III was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Example 5
In Example 2， the lipase Lipozyme RM IM was replaced with lipase D (Amano Enzyme Manufacturing Ltd) ， and other conditions were identical to those in Example 2. An oil/fat composition IV was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Example 6
In Example 2， oleic acid was replaced with ethyl oleate， and other conditions were identical to those in Example 2. An oil/fat composition V was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Comparative Example 2
In Example 2， no glycerol was added to the mixture of the refined oil/fat and oleic acid， and other conditions were identical to those in Example 2. An oil/fat composition VI was finally obtained. The FAC of  the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 1.
Table 1
Figure PCTCN2015098459-appb-000003
Note：
Sn-2 position palmitic acid/total palmitic acid (％) ＝Sn-2 position palmitic acid content (％) / (3×total palmitic acid content (％) ) ×100％
*Others are C12： 0， C14： 0， and C18： 3.
Example 7
Step 1
To 500g palm oil (IV＝52) was added Lipozyme TL IM (Novozymes  Company) in an amount of 6％by weight of the oil/fat. The mixture was reacted at 6 5℃for 24h to conduct the randomization， and filtered to obtain a randomized oil/fat. The randomized oil/fat was heated to 105℃， and stirred in vacuum for 30min to conduct the drying. Activated clay was added in an amount of 2％by wei ght of the above dried mixture. The resulting mixture was kept at 110℃for 30min to conduct the decolorizaion， and filtered to obtain a decolored oil/fat. The oil/fat was heated to 240℃， and deodorized at 2mbar in a purge of nitrogen for 3h to obtain a refined oil/fat 2.
Step 2
500g of the refined oil/fat 2 and oleic acid were mixed in a weight ratio of 1∶2. Glycerol was added in an amount of 3％by the total weight of the refined oil/fat 2 and oleic acid. The resulting mixture was passed through a packed bed containing 100g Lipozyme RM IM to conduct an enzymatic directed interesterification. The reaction temperature was 60℃， and the flow rate was 150g/h. The oil/fat from the enzyme column was collected to obtain an oil/fat composition VII. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 2.
Comparative Example 3
In step 2 of Example 3， no glycerol was added in the mixture of the refined oil/fat and oleic acid， and other conditions were identical to those in Example 3. An oil/fat composition VIII was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 2.
Table 2
Figure PCTCN2015098459-appb-000004
Note：
Sn-2 position palmitic acid/total palmitic acid (％) ＝Sn-2 position palmitic acid content (％) / (3×total palmitic acid content (％) ) ×100％
*Others are C12： 0， C14： 0， and C18： 3.
Example 8
In Step 2 of Example 1， 1， 2-propylene glycol was added to the mixture of the refined oil/fat and oleic acid in an amount of 5％by the total weight of the mixture， and other conditions were identical to those in Example 1. An oil/fat composition IX was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 3.
Example 9
In Step 2 of Example 1， 1， 2-propylene glycol was added to the mixture of the refined oil/fat and oleic acid in an amount of 10％by the total weight of the mixture， and other conditions were identical to those in Example 1. An oil/fat composition X was finally obtained. The FAC of the  triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 3.
Table 3
Figure PCTCN2015098459-appb-000005
Note：
Sn-2 position palmitic acid/total palmitic acid (％) ＝Sn-2 position palmitic acid content (％) / (3×total palmitic acid content (％) ) ×100％
*Others are C12： 0， C14： 0， and C18： 3.
Example 10
In Step 2 of Example 1， erythritol was added to the mixture of the refined oil/fat and oleic acid in an amount of 5％by the total weight of the mixture， and other conditions were identical to those in Example 1. An oil/fat composition XI was finally obtained. The FAC of the triglyceride product and the content of the fatty acid at Sn-2 position were measured. The result was shown in Table 4.
Table 4
Figure PCTCN2015098459-appb-000006
Note：
Sn-2 position palmitic acid/total palmitic acid (％) ＝Sn-2 position palmitic acid content (％) / (3×total palmitic acid content (％) ) ×100％
*Others are C12： 0， C14： 0， and C18： 3.
The above examples showed that the addition of polyol in the enzymatic interesterification can effectively increase the ratio of saturated fatty acid at Sn-2 position to the total saturated fatty acid in the product， in particular the ratio of palmitic acid at Sn-2 position to the total palmitic acid in the human milk fat substitute. The method of the present invention may be adaptable for the enzymatic interesterification with different starting materials. In the oil/fat compositions obtained in the above examples of the present invention， the saturated fatty acids were mainly bound at Sn-2 position of the triglyceride， for example， the ratio of the palmitic acid residue at Sn-2 position to the total palmitic acid residue was at least 52％， preferably 52-70％， more preferably 54-68％， further preferably 59-65％. The unsaturated fatty acid residues at Sn-1 and Sn-3  positions of the triglyceride were the oleic acid residue or the linoleic acid residue. The oil/fat composition of the present invention is very similar to the oil/fat in the human milk with respect to the triglyceride structure. Therefore， the use of the oil/fat composition of the present invention as the human milk fat substitute can have an advantage such as promoting the absorption of the fat in infant and young child and increasing the absorption of the mineral substances.

Claims (14)

  1. A preparation method for an oil/fat composition or a human milk fat substitute， wherein a triglyceride and a fatty acid or a derivative thereof are contacted in the presence of a lipase， wherein a polyol is present in the system.
  2. The preparation method according to claim 1， wherein the method comprises a step of a triglyceride and a fatty acid or a derivative thereof being subjected to a directed interesterification in the presence of a specific lipase， wherein said polyol is optionally added to the reaction system before the interesterification or during the interesterification.
  3. The preparation method according to claim 2， wherein said triglyceride contains a triglyceride represented by general formula (1) ，
    Figure PCTCN2015098459-appb-100001
    in said general formula (1) ， R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight-chain or branched， saturated fatty acids containing 8-30 carbon atoms.
  4. The preparation method according to claim 3， wherein said triglyceride is vegetable-derived.
  5. The preparation method according to claim 4， wherein said R1， R2 and R3 are each identical or different， at least one of R1， R2 and R3 represents a group derived from straight saturated fatty acids containing 16-18 carbon atoms. 6. The preparation method according to claim 5， wherein said polyol is a 2-to 6-membered alcohol.
  6. The preparation method according to claim 6， wherein based on the total amount of said triglyceride and the fatty acid or a derivative thereof， the amount of said polyol is 1-30wt％.
  7. The preparation method according to claim 7， wherein said fatty  acid is at least one member selected from the group consisting of straight-chain unsaturated fatty acids containing 16-20 carbon atoms， and said fatty acid derivative is at least one member selected from the group consisting of esters of a straight-chain unsaturated fatty acid containing 16-20 carbon atoms.
  8. The preparation method for according to claim 8， wherein said specific lipase is a 1， 3-specific lipase.
  9. The preparation method according to claim 4， wherein said triglyceride is at least one member selected from the group consisting of a vegetable oil stearin containing palmitoyl triglyceride， a vegetable oil containing palmitoyl triglyceride and a randomly interesterified oil/fat of a vegetable oil containing palmitoyl triglyceride.
  10. The preparation method according to claim 10， wherein said triglyceride is at least one of palm oil stearin， palm oil， palm oil fractionation， randomly interesterified palm oil stearin， randomly interesterified palm oil， and randomly interesterified palm oil fractionation.
  11. The preparation method according to claim 8， wherein said fatty acid or a derivative thereof is at least one member selected from the group consisting of oleic acid， ethyl oleate， methyl oleate， high oleic sunflower seed oil and high oleic palm oil.
  12. The preparation method according to claim 5， wherein said polyol is at least one member selected from the group consisting of ethylene glycol， propylene glycol， glycerol， trimethylolethane， erythritol， pentaerythritol， sorbitol and xylitol.
  13. An oil/fat composition or a human milk fat substitute prepared with the preparation method for an oil/fat composition or a human milk fat substitute according to claim 1.
  14. A formula milk powder for infant and young child， a formula food for for infant and young child， a substitute for human milk fat composition or a dietary ingredient， which contains the oil/fat composition or the human milk fat substitute according to claim 14.
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