WO2016004825A1 - Composition comprising 2-palmitic acid glyceride and preparation method thereof, structural fat comprising 1, 3-diunsaturated fatty acid-2-palmitic acid and preparation method, and special food - Google Patents

Composition comprising 2-palmitic acid glyceride and preparation method thereof, structural fat comprising 1, 3-diunsaturated fatty acid-2-palmitic acid and preparation method, and special food Download PDF

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WO2016004825A1
WO2016004825A1 PCT/CN2015/082488 CN2015082488W WO2016004825A1 WO 2016004825 A1 WO2016004825 A1 WO 2016004825A1 CN 2015082488 W CN2015082488 W CN 2015082488W WO 2016004825 A1 WO2016004825 A1 WO 2016004825A1
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palmitic acid
glyceride
acid
oil
composition containing
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PCT/CN2015/082488
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French (fr)
Chinese (zh)
Inventor
李翔宇
胡迎春
汪志明
陆姝欢
周强
汪锋
肖敏
易德伟
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嘉必优生物工程（武汉）有限公司
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Priority claimed from CN201410319597.6A external-priority patent/CN104087626A/en
Priority claimed from CN201510220956.7A external-priority patent/CN104830545B/en
Application filed by 嘉必优生物工程（武汉）有限公司 filed Critical 嘉必优生物工程（武汉）有限公司
Publication of WO2016004825A1 publication Critical patent/WO2016004825A1/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
    • C11C3/10—Ester interchange
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats

Definitions

  • the present invention relates to a structural oil and fat, and more particularly to a composition containing 2-palmitic acid glyceride and a preparation method thereof, and relates to a structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid and a preparation method thereof It also involves a special diet.
  • This application is based on the Chinese invention patent application whose application date is July 7, 2014, application number 201410319597.6, and the Chinese invention patent application whose application date is May 5, 2015, and the application number is CN201510220956.7. This article is incorporated herein by reference.
  • Triglycerides are the major lipid components ingested by humans. Modern nutrition has confirmed that in the process of digesting triglycerides, the human body preferentially hydrolyzes the fatty acids in the Sn-1, 3 positions to form 2-monoglycerides and a large amount of free fatty acids. These free fatty acids will have two kinds of reactions in the body: 1. They are absorbed by themselves; 2. They are discharged after reacting with other substances in the body. Studies have shown that compared with free unsaturated fatty acids, free saturated fatty acids have a slow absorption rate and are more likely to react with calcium to form insoluble calcium soap, which is then excreted.
  • triglycerides which produce free unsaturated fatty acids are more beneficial to human body absorption than triglycerides which produce free saturated fatty acids.
  • the edible oils are mainly derived from plants.
  • the saturated fatty acids are mainly distributed in sn-1, 3, and the human body not only loses a lot of fat and calcium during the digestion process, but also produces calcium soap which increases the hardness of the feces. It causes constipation and abdominal pain in some people, and even causes intestinal obstruction. If the saturated fatty acid is concentrated in the sn-2 position of triglyceride (also called "2 position”), this problem can be effectively solved, especially for individuals with weak body and poor gastrointestinal function.
  • triglycerides In breast milk, about 98% of fat is in the form of triglycerides, of which palmitic acid (Palmitic) Acid, C16:0, saturated fatty acid) content of about 20% to 25%, oleic acid (oleic Acid, C18:1, unsaturated fatty acid) content of about 30% to 38%. Further, most of the palmitic acid is distributed in the 2 position of the triglyceride, while the oleic acid is mainly distributed in the Sn-1 and Sn-3 positions.
  • This unique triglyceride structure in the breast milk is called 2- Palmitic acid glyceride.
  • the content of infant formula and breast milk in the market is relatively close. However, a large number of human experiments and animal experiments have confirmed that breast milk fat absorption is superior to infant formula, one of the important reasons is unique in breast milk. Triglyceride structure.
  • Chinese patent CN102229866B discloses a process for preparing a low cholesterol, high 2-palmitoyl glyceride composition by using lard as a raw material and using a 1,3 position selective lipase-catalyzed acid hydrolysis process.
  • the composition of lard is complex, so the preparation process is complicated, and the practical application may be limited by religious or national beliefs.
  • Chinese Patent No. CN101258230B discloses a process for obtaining 2-palmitic acid glyceride by enzymatic transesterification of palm oil stearin with an iodine value (IV) of 8-12 and an ester of oleic acid or a non-glyceride thereof.
  • Chinese Patent No. CN101679909B also discloses a method for obtaining a 2-palmitic acid glyceride composition mainly by using one or more palm oils containing tripalmitoyl glyceride and having an iodine value of from about 18 to about 40.
  • the structural oil containing 2-palmitic acid glyceride is characterized in that the fatty acid at the Sn-2 position is mainly palmitic acid, and the fatty acid at the first and third positions is mainly unsaturated fatty acid (unsaturated). Fatty acid, UFA).
  • Glycidol and chloropropanol are a class of contaminants that have been of international interest in recent years, among which chloropropanol can be converted by glycidol. These two contaminants are genotoxic and nephrotoxic and are possible carcinogens. In 2009, Kao Corporation of Japan stopped selling the Econa series of grease products because of the high content of glycidol and chloropropanol.
  • 1-Chloro-1,2-propanediol has been identified as a process-induced secondary component in fully refined fats and oils, which are formed primarily in the deodorization step and which exhibit at least two isomers, That is, 2-chloro-1,2-propanediol and 3-chloro-1,2-propanediol, and the latter is the main isomer, and all of the fully refined fats and oils contain 3-chloro-1,2-propanediol.
  • processing temperatures, particularly steam deodorization processes have a large effect: the higher the temperature, the higher the amount of 3-chloro-1,2-propanediol found in vegetable oils.
  • One of the technical problems to be solved by the present invention is to provide a novel method for preparing a composition containing 2-palmitic acid glyceride.
  • a second technical problem to be solved by the present invention is to provide a composition containing 2-palmitic acid glyceride prepared by the above method.
  • the third technical problem to be solved by the present invention is to provide a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid which is highly safe to eat.
  • the fourth technical problem to be solved by the present invention is to provide a method for preparing the above structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
  • a fifth technical problem to be solved by the present invention is to provide a special diet containing the above-mentioned structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
  • the preparation method of the composition containing 2-palmitic acid glyceride comprises the steps of: (1) providing a glyceride containing a palmitic acid residue; (2) providing a palmitic acid residue. Glyceride is mixed with palmitic acid, palmitate or palmitic acid non-glyceride for transesterification to obtain oil A; (3) lipid A and unsaturated fatty acid or its non-glyceride are subjected to Sn-1, enzymatically oriented ester at position 3 The mixture was exchanged to obtain a mixed oil B; (4) The mixed oil B was purified to obtain a composition containing 2-palmitic acid glyceride.
  • the palmitate comprises sodium palmitate or potassium palmitate, and the weight ratio of palmitate to glyceride containing palmitic acid residues is no more than 4:1, preferably 1:500 to 4:1, more preferably 1:50 to 1:1.
  • the palmitic acid non-glyceride comprises methyl palmitate or ethyl palmitate, and the weight ratio of palmitic acid non-glyceride to glyceride containing palmitic acid residues is not more than 4:1, preferably 1:500 to 4: 1, more preferably from 1:50 to 1:1.
  • the weight ratio of palmitic acid to glyceride containing palmitic acid residues is no more than 4:1, preferably 1:500 to 4:1, more preferably 1:50 to 1:1.
  • water is further added, and the specific gravity of water and the glyceride containing palmitic acid residues is less than 5% by weight, preferably less than 2% by weight, more preferably less than 1% by weight.
  • a lipase may be added, and the specific gravity of the lipase and the glyceride containing the palmitic acid residue is 1% by weight to 50% by weight.
  • the oil and fat A is obtained by refining.
  • the weight ratio of the fat A to the unsaturated fatty acid or its non-glyceride is from 2:1 to 1:10, preferably from 1:1 to 1:3.
  • a solvent further comprising hexane, cyclohexane, octane or isooctane is further added.
  • the unsaturated fatty acid in the step (3) includes oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid.
  • the present invention also provides a composition containing 2-palmitic acid glyceride prepared by the above method.
  • the structural grease containing 1,3-diunsaturated fatty acid-2-palmitic acid provided by the invention has a triglyceride content of not less than 90%, and the total content of 3-chloro-1,2-propanediol and glycidol is not It is higher than 1.8 mg/kg, and the content of 3-chloro-1,2-propanediol is not more than 1.2 mg/kg.
  • the structural fat of the 1,3-diunsaturated fatty acid-2-palmitic acid of the present invention the total content of 3-chloro-1,2-propanediol and glycidol is not more than 0.5 mg/kg, and 3- The content of chloro-1,2-propanediol is not higher than 0.4 mg/kg.
  • the structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid of the present invention has a low content of 3-chloro-1,2-propanediol, and 3-chloro-1,2-propanediol and glycidol The total content is also low, so the food safety is high.
  • the present invention also provides a method for preparing a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid, comprising: providing a vegetable oil containing a palmitic acid residue which has not been deodorized; and containing a palmitic acid residue
  • the vegetable oil oil and the unsaturated fatty acid or its non-glyceride are subjected to the enzymatic transesterification of the Sn-1, 3 position to obtain a mixed oil; the mixed oil is refined to obtain the 1,3-diunsaturated fatty acid-2-palm Acid structure oil.
  • the invention also provides a special diet comprising the above-mentioned structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid, the special diet is infant formula, infant formula rice flour, child milk, children's yogurt and digestive dysfunction patients Nutritional meal.
  • the invention provides a novel preparation method comprising a 2-palmitic acid glyceride composition, which has a simple preparation process.
  • the product obtained by the method of the present invention has higher palmitic acid content and less by-products after preparation, thereby contributing to environmental protection.
  • the raw material used in the method for preparing a structural fat or oil containing 1,3-di-unsaturated fatty acid-2-palmitic acid is easily available, and the entire step is simple, so that it can be adapted to the needs of large-scale industrial production.
  • Figure 1 is a formulation of a special diet prepared using a composition containing 2-palmitic acid glyceride.
  • Fig. 2 is a formulation table for preparing a special diet using a structural fat containing 1,3-diunsaturated fatty acid-2-palmitic acid.
  • a palm oil having a ratio of palmitic acid to total fatty acid of 21.7% and a palmitic acid content of 15.6%.
  • 2 palmitic acid content refers to the content of all fatty acids in the 2 position of palmitic acid at the 2 position, and the detection method thereof refers to GB/T24894, the same below.
  • the mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a composition containing 2-palmitic acid glyceride, which is passed through a GC (high temperature capillary column, FID detection). , the same as below) and thin layer chromatography to detect the content of palmitic acid at position 2 20.1 wt%.
  • the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-dioleic acid-2-palmitic acid.
  • the content of 1,3-dioleic acid-2-palmitic acid in the structural oil was 15.4% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.64 mg/kg, wherein 3- The content of chloro-1,2-propanediol was 1.03 mg/kg.
  • the mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the content of palmitic acid is 21.0 wt%.
  • the 2-palmitic acid glyceride-containing composition is a structural fat or oil containing 1,3-dilinoleic acid-2-palmitic acid.
  • the content of 1,3-dilinoleic acid-2-palmitic acid in the structural oil is 10.9 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 1.01 mg/kg, wherein The content of 3-chloro-1,2-propanediol was 0.68 mg/kg.
  • a shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, by GC and thin layer chromatography. Detection of 2 palmitic acid content is 49wt%.
  • the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-diarachidonic acid-2-palmitic acid.
  • the content of the structure oil 1,3-diarachidonic acid-2-palmitic acid was 27.9% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.11 mg/kg, of which 3 The content of -chloro-1,2-propanediol was 0.74 mg/kg.
  • a shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, by GC and thin layer chromatography. Detection of 2 palmitic acid content is 20.1 wt%.
  • a shortening is provided in which palmitic acid accounts for 23% of total fatty acids and 2 palmitic acid content is 16.9%.
  • reaction substrate shortening 2000 g, ethyl palmitate 500 g, and lipase 1000 g were placed in a container, heated to 50 ° C under nitrogen atmosphere and kept constant, and the reaction was continued for 5 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 26.6%.
  • a shortening is provided in which palmitic acid accounts for 42.4% of total fatty acids and 2 palmitic acid content is 31.5%.
  • reaction substrate palm oil stearin 240 g, sodium palmitate 24 g, and deionized water 12 g were placed in a flask, heated to 190 ° C under nitrogen atmosphere and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, 600 mL of acetone was sufficiently dissolved, and then the fatty acid sodium was centrifuged to obtain a fat or oil A.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 40.2% by weight.
  • the composition containing 2-palmitic acid glyceride is a structural oil containing 1,3-dicosapentaenoic acid-2-palmitic acid, and the 1,3-dicosapentaene of the structural oil is detected by detection.
  • the content of acid-2-palmitic acid was 24.9% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.55 mg/kg, and the content of 3-chloro-1,2-propanediol was 1.01 mg/ Kg.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 45.4% by weight.
  • the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-didocosahexaenoic acid-2-palmitic acid, and the 1,3-t22 carbon of the structural fat is detected by the detection.
  • the content of hexenoic acid-2-palmitic acid is 28.6% by weight, the total content of 3-chloro-1,2-propanediol and glycidol is 1.69 mg/kg, and the content of 3-chloro-1,2-propanediol is 1.15. Mg/kg.
  • reaction substrate palm oil stearin 3000 g, lipase 100 g, and deionized water 12.5 g were placed in a flask, and nitrogen gas was added thereto, and the mixture was heated to 160 ° C with stirring to keep the reaction constant for 30 hours. After the reaction was completed, the fat A was obtained.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 38.4% by weight.
  • the palmitic acid content of the final product in the final product is improved.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 63.3 wt%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 62.0% by weight.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 68.2% by weight.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 56.5 wt%.
  • the palmitic acid content of the final product in the final product is improved.
  • a palm oil stearin is provided, which has a ratio of palmitic acid to total fatty acid of 62.3% and a palmitic acid content of 44.4%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 58.1% by weight.
  • reaction substrate palm oil stearin 5000 g, potassium palmitate 150 g, and deionized water 12 g were placed in a container, stirred and heated to 220 ° C and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, 16 L of acetone was sufficiently dissolved, and the soap was removed by centrifugal filtration (the content of the soap was less than 10 ppm) to obtain a fat and oil A.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 59.2% by weight.
  • the composition containing 2-palmitic acid glyceride is a structural oil containing 1,3-dilinolenic acid-2-palmitic acid, and the content of 1,3-dilinolenic acid-2-palmitic acid is 34.4wt by detection.
  • the total content of %, 3-chloro-1,2-propanediol and glycidol was 1.76 mg/kg, and the content of 3-chloro-1,2-propanediol was 1.10 mg/kg.
  • a palm oil stearin having a ratio of palmitic acid to total fatty acid of 71.5% and a palmitic acid content of 55.6%.
  • reaction substrate palm oil stearin 10000 g, sodium palmitate 20 g, and deionized water 12 g were placed in a container, and the mixture was heated to 160 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the fatty acid ethyl ester by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content at the 2 position was 63.1% by weight.
  • a shortening is provided, in which palmitic acid accounts for 16.5% of total fatty acids, and 2 palmitic acid content is 13.3%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content was 21.1% by weight.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content at the 2-position was 50.8 wt%.
  • a shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content at the 2-position was 52.6 wt%.
  • a shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography.
  • the palmitic acid content at the 2 position was 63.3 wt%.
  • an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 22.1% and a palmitic acid content of 14.6%.
  • the mixed oil is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and performing dry fractionation to remove the free fatty acid, and deodorizing to obtain a structural oil containing 1,3-dilinoleic acid-2-palmitic acid, and detecting,
  • the content of 1,3-dilinoleic acid-2-palmitic acid is 6.8 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.28 mg/kg, wherein 3-chloro-1,2
  • the content of propylene glycol was 0.18 mg/kg.
  • an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 23.7% and a palmitic acid content of 14.9%.
  • the mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a structural fat containing 1,3-diarachidonic acid-2-palmitic acid. .
  • the content of 1,3-dirachidotetraenoic acid-2-palmitic acid is 13.7% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.24 mg/kg, wherein 3-chloro The content of -1,2-propanediol was 0.16 mg/kg.
  • An undeodorized palm oil which has a palmitic acid ratio of 40.4% of total fatty acids and a palmitic acid content of 29.5%.
  • the mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dicosapentaenoic acid-2-palmitic acid.
  • the content of 1,3-docosapentaenoic acid-2-palmitic acid is 23.8 wt%
  • the total content of 3-chloro-1,2-propanediol and glycidol is 0.49 mg/kg, wherein The content of 3-chloro-1,2-propanediol is 0.35 mg/kg. .
  • an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 45.7% and a palmitic acid content of 33.8%.
  • the mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dopencosyl-2-enoic acid-2-palmitic acid
  • the purification steps include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dopencosyl-2-enoic acid-2-palmitic acid
  • the content of 1,3-docosahexaenoic acid-2-palmitic acid is 29.7% by weight
  • the total content of 3-chloro-1,2-propanediol and glycidol is 0.4 mg/kg.
  • the content of 3-chloro-1,2-propanediol was 0.29 mg/kg.
  • an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 75.7% and a palmitic acid content of 60.3%.
  • the mixed oil B is purified, and the steps of purification include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dilinolenic acid-2-palmitic acid, which is detected.
  • the content of 1,3-dilinolenic acid-2-palmitic acid is 61.5 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.44 mg/kg, wherein 3-chloro-1,2-propanediol The content is 0.32mg/kg .
  • An undeodorized palm oil which has a ratio of palmitic acid to total fatty acid of 62.9% and a palmitic acid content of 44.9%.
  • the mixed oil is purified, and the steps of purification include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural oil containing 1,3-dioleic acid-2-palmitic acid, which is detected by 1 , the content of 3-dioleic acid-2-palmitic acid is 32.3 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.15 mg/kg, wherein 3-chloro-1,2-propanediol The content is 0.10 mg/kg.
  • the method for preparing the structural fat and oil containing the 1,3-diunsaturated fatty acid-2-palmitic acid has the advantages of simple steps, reliable and feasible, and can meet the needs of large-scale industrial production. Further, the structural oil obtained by the method of the present invention has a very low content of 3-chloro-1,2-propanediol and glycidol, so that it is safer to eat.
  • composition containing 2-palmitic acid glyceride prepared by the above method can be used in the fields of infant formula, infant formula rice powder, child milk, children's yogurt and special diet for patients with digestive dysfunction, and the following only for patients with digestive dysfunction
  • the use of a composition containing a 2-palmitic acid glyceride of the present invention is described in detail by taking a special diet as an example.
  • the composition containing 2-palmitic acid glyceride prepared in the above Example 5 was formulated in accordance with the formulation shown in Fig. 1.
  • the rice is first pulverized to obtain about 100 to 120 mesh rice flour.
  • a slurry of 45% solid matter was prepared, and after shearing at 5000 rpm for 25 minutes, it was homogenized at 20 MPa to obtain a homogenized slurry. It was then hydrolyzed with 0.8% amylase for 4 hr and then gelatinized at 85 ° C for 45 min.
  • the gelatinized slurry was subjected to steam drum drying according to the following parameters: a steam pressure of 0.45 MPa, a drum rotation speed of 4 rpm, and a film thickness of 2.5 mm.
  • a special dietary rice powder containing 2-palmitic acid glyceride having a moisture content of about 3% can be finally obtained.
  • the above-mentioned structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid can be used in the fields of infant formula, infant formula rice flour, child milk, children's yogurt and nutritional diet of patients with digestive dysfunction, etc.
  • the nutrient diet of a patient with digestive dysfunction is taken as an example to describe in detail the application of the 1,3-diunsaturated fatty acid-2-palmitic acid-containing structural oil of the present invention.
  • the structural grease containing 1,3-diunsaturated fatty acid-2-palmitic acid obtained by using any of the above examples was formulated according to the formulation shown in FIG.
  • the rice is first pulverized to obtain about 100 to 120 mesh rice flour.
  • a slurry of 45% solid matter was prepared, and after shearing at 5000 rpm for 25 minutes, it was homogenized at 20 MPa to obtain a homogenized slurry. It was then hydrolyzed with 0.8% amylase for 4 hr and then gelatinized at 85 ° C for 45 min.
  • the gelatinized slurry was subjected to steam drum drying according to the following parameters: a steam pressure of 0.45 MPa, a drum rotation speed of 4 rpm, and a film thickness of 2.5 mm.

Abstract

Provided are a composition comprising 2-palmitic acid glyceride and a preparation method thereof, and further provided are a structural fat comprising 1, 3-diunsaturated fatty acid-2-palmitic acid and a preparation method. The preparation method of the composition comprises: (1) providing a glyceride comprising a palmitic acid residue; (2) mixing the glyceride comprising the palmitic acid residue with palmitic acid, a salt thereof or a palmitic acid nonglyceride to conduct ester exchange so as to obtain an oil A; (3) conducting Sn-1, 3 site enzymatic directed interesterification on the oil A and the unsaturated fatty acid or the nonglyceride thereof so as to obtain a mixed oil B; and (4) refining the mixed oil B to obtain the composition comprising 2-palmitic acid glyceride.

Description

含有2-棕榈酸甘油酯的组合物及其制备方法、含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂及制备方法、特殊膳食  Composition containing 2-palmitic acid glyceride, preparation method thereof, structural oil and fat containing 1,3-diunsaturated fatty acid-2-palmitic acid, preparation method and special diet 技术领域Technical field
本发明涉及一种结构油脂，尤其是涉及一种含有2-棕榈酸甘油酯的组合物及其制备方法，并涉及含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂及制备方法，还涉及一种特殊膳食。本申请是基于申请日为2014年7月7日，申请号为201410319597.6的中国发明专利申请以及申请日为2015年5月5日，申请号为CN201510220956.7的中国发明专利申请，该申请的内容引入本文作为参考。 The present invention relates to a structural oil and fat, and more particularly to a composition containing 2-palmitic acid glyceride and a preparation method thereof, and relates to a structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid and a preparation method thereof It also involves a special diet. This application is based on the Chinese invention patent application whose application date is July 7, 2014, application number 201410319597.6, and the Chinese invention patent application whose application date is May 5, 2015, and the application number is CN201510220956.7. This article is incorporated herein by reference.
背景技术Background technique
甘油三酯为人类摄取的主要油脂组成。现代营养学已经证实，人体在消化甘油三酯的过程中，会优先水解Sn-1,3位上的脂肪酸，形成2-单甘酯与大量的游离脂肪酸。这些游离脂肪酸在体内会出现两种反应：1、被自身吸收；2、与体内其他物质反应后被排出。研究表明，与游离不饱和脂肪酸相比，游离饱和脂肪酸吸收速率慢，更容易与钙发生反应，形成不溶性的皂钙，进而被排出体外。由此可见，相对于产生游离饱和脂肪酸的甘油三酯，产生游离不饱和脂肪酸的甘油三酯更利于人体的吸收。目前市售的食用油主要来源于植物，其饱和脂肪酸主要分布在sn-1,3位，人体在消化过程中，不但流失了大量的脂肪和钙，而且其生成的皂钙会增加粪便的硬度，导致部分人群便秘和腹痛，甚至引发肠梗阻。若将饱和脂肪酸集中于甘油三酯的sn-2位（也称为“2位”），则能有效解决这个问题，尤其是对于身体虚弱，肠胃功能不好的个体来说，效果更加明显。Triglycerides are the major lipid components ingested by humans. Modern nutrition has confirmed that in the process of digesting triglycerides, the human body preferentially hydrolyzes the fatty acids in the Sn-1, 3 positions to form 2-monoglycerides and a large amount of free fatty acids. These free fatty acids will have two kinds of reactions in the body: 1. They are absorbed by themselves; 2. They are discharged after reacting with other substances in the body. Studies have shown that compared with free unsaturated fatty acids, free saturated fatty acids have a slow absorption rate and are more likely to react with calcium to form insoluble calcium soap, which is then excreted. It can be seen that triglycerides which produce free unsaturated fatty acids are more beneficial to human body absorption than triglycerides which produce free saturated fatty acids. Currently, the edible oils are mainly derived from plants. The saturated fatty acids are mainly distributed in sn-1, 3, and the human body not only loses a lot of fat and calcium during the digestion process, but also produces calcium soap which increases the hardness of the feces. It causes constipation and abdominal pain in some people, and even causes intestinal obstruction. If the saturated fatty acid is concentrated in the sn-2 position of triglyceride (also called "2 position"), this problem can be effectively solved, especially for individuals with weak body and poor gastrointestinal function.
在母乳中，98%左右的脂肪以甘油三酯的形式存在，其中棕榈酸（Palmitic acid，C16:0，饱和脂肪酸）的含量约占20%至25%，油酸（oleic acid，C18:1，不饱和脂肪酸）含量约占30%至38%。更进一步的，大部分的棕榈酸分布在甘油三酯的2位，而油酸则主要分布在Sn-1和Sn-3位上，母乳中这种独特的甘油三酯结构被称为2-棕榈酸甘油酯。目前，市场上的婴幼儿配方奶粉与母乳的成分含量比较接近，但是，大量的人体试验和动物实验都已证实，母乳脂肪的吸收优于婴幼儿配方奶粉，其中一个重要原因就在于母乳中独特的甘油三酯结构。In breast milk, about 98% of fat is in the form of triglycerides, of which palmitic acid (Palmitic) Acid, C16:0, saturated fatty acid) content of about 20% to 25%, oleic acid (oleic Acid, C18:1, unsaturated fatty acid) content of about 30% to 38%. Further, most of the palmitic acid is distributed in the 2 position of the triglyceride, while the oleic acid is mainly distributed in the Sn-1 and Sn-3 positions. This unique triglyceride structure in the breast milk is called 2- Palmitic acid glyceride. At present, the content of infant formula and breast milk in the market is relatively close. However, a large number of human experiments and animal experiments have confirmed that breast milk fat absorption is superior to infant formula, one of the important reasons is unique in breast milk. Triglyceride structure.
受到母乳中独特的甘油三酯结构的启发，目前已经有部分厂商利用对天然油脂的改性来生产含有2-棕榈酸甘油酯的组合物，并将其添加到婴幼儿奶粉及特殊膳食中，这不但可以提高人体对脂肪和钙的吸收效率，还能降低粪便的硬度，减少便秘和肠梗阻的发生概率。Inspired by the unique triglyceride structure in breast milk, some manufacturers have used the modification of natural oils to produce a composition containing 2-palmitic acid glyceride and added it to infant formula and special diets. This not only improves the body's absorption of fat and calcium, but also reduces the hardness of the stool and reduces the incidence of constipation and intestinal obstruction.
中国授权专利CN102229866B公开了一种利用猪油为原料，采用1,3位置选择性脂肪酶催化酸解工艺，制备得到低胆固醇，高2-棕榈酸甘油酯组合物的工艺方法。但猪油成分复杂，因此制备工艺复杂，而且实际应用中还可能受到宗教或民族信仰的限制。Chinese patent CN102229866B discloses a process for preparing a low cholesterol, high 2-palmitoyl glyceride composition by using lard as a raw material and using a 1,3 position selective lipase-catalyzed acid hydrolysis process. However, the composition of lard is complex, so the preparation process is complicated, and the practical application may be limited by religious or national beliefs.
中国授权专利CN101258230B公开了一种通过使碘值（IV）为8-12的棕榈油硬脂精与油酸或其非甘油酯的酯进行酶促酯交换获得2-棕榈酸甘油酯的方法。中国授权专利CN101679909B也公开了一种获得2-棕榈酸甘油酯组合物的方法，该方法主要是通过将一种或多种包含三棕榈酰甘油酯，碘值为约18到约40的棕榈油硬脂酸甘油酯组分进行随机酯交换后，与油酸或其非甘油酯在1,3位专一性酶的作用下进行酶促酯交换反应后，分离棕榈酸或棕榈酸非甘油酯后制得目标产物。但是这些方法受到原料的限制，产品的纯度都比较低。即使通过随机酯交换提高了 2位上棕榈酸的含量，但由于棕榈酸总组成的限制，产品的纯度依然不高。这样的组合物在进行后续精制的时候，会产生大量的废弃物，如脂肪酸钠等，不利于环保。Chinese Patent No. CN101258230B discloses a process for obtaining 2-palmitic acid glyceride by enzymatic transesterification of palm oil stearin with an iodine value (IV) of 8-12 and an ester of oleic acid or a non-glyceride thereof. Chinese Patent No. CN101679909B also discloses a method for obtaining a 2-palmitic acid glyceride composition mainly by using one or more palm oils containing tripalmitoyl glyceride and having an iodine value of from about 18 to about 40. After random transesterification of the glyceryl stearate component, separation of palmitic acid or palmitic acid non-glyceride after enzymatic transesterification with oleic acid or its non-glycerol ester under the action of a specific enzyme of 1,3 The target product is obtained afterwards. However, these methods are limited by the raw materials, and the purity of the products is relatively low. Even improved by random transesterification The content of palmitic acid in the 2nd position, but due to the limitation of the total composition of palmitic acid, the purity of the product is still not high. Such a composition generates a large amount of waste, such as sodium fatty acid, during subsequent purification, which is not environmentally friendly.
并且，含有2-棕榈酸甘油酯的结构油脂的特点在于Sn-2位上的脂肪酸主要为棕榈酸，1,3位上的脂肪酸主要为不饱和脂肪酸（unsaturated fatty acid， UFA）。Moreover, the structural oil containing 2-palmitic acid glyceride is characterized in that the fatty acid at the Sn-2 position is mainly palmitic acid, and the fatty acid at the first and third positions is mainly unsaturated fatty acid (unsaturated). Fatty acid, UFA).
缩水甘油（酯）、氯丙醇（酯）是近年来国际上开始关注的一类污染物,其中氯丙醇（酯）可由缩水甘油（酯）转化。这两种污染物具有遗传毒性和肾脏毒性，是可能的致癌物。2009年日本花王公司停止Econa系列油脂产品的销售，就是因为缩水甘油（酯）及氯丙醇（酯）的含量过高问题。 Glycidol and chloropropanol are a class of contaminants that have been of international interest in recent years, among which chloropropanol can be converted by glycidol. These two contaminants are genotoxic and nephrotoxic and are possible carcinogens. In 2009, Kao Corporation of Japan stopped selling the Econa series of grease products because of the high content of glycidol and chloropropanol.
1-氯-1,2-丙二醇已经被鉴定为完全精制的脂肪和油中的加工诱导的次要组分，它们主要是在脱臭步骤中形成的，并且至少显示出形成两种异构体，即2-氯-1,2-丙二醇和3-氯-1,2-丙二醇，且后者是主要的异构体，所有完全精制的脂肪和油均含有3-氯-1,2-丙二醇。虽然尚未完全理解它的确切形成过程，但是已经观察到加工温度、特别是蒸汽脱臭加工具有很大影响：温度越高，植物油中发现的3-氯-1,2-丙二醇的量越高。1-Chloro-1,2-propanediol has been identified as a process-induced secondary component in fully refined fats and oils, which are formed primarily in the deodorization step and which exhibit at least two isomers, That is, 2-chloro-1,2-propanediol and 3-chloro-1,2-propanediol, and the latter is the main isomer, and all of the fully refined fats and oils contain 3-chloro-1,2-propanediol. Although its exact formation process has not been fully understood, it has been observed that processing temperatures, particularly steam deodorization processes, have a large effect: the higher the temperature, the higher the amount of 3-chloro-1,2-propanediol found in vegetable oils.
技术问题technical problem
本发明所要解决的技术问题之一在于提供一种新的含有2-棕榈酸甘油酯的组合物的制备方法。One of the technical problems to be solved by the present invention is to provide a novel method for preparing a composition containing 2-palmitic acid glyceride.
本发明所要解决的技术问题之二在于提供一种由上述方法制备的含有2-棕榈酸甘油酯的组合物。A second technical problem to be solved by the present invention is to provide a composition containing 2-palmitic acid glyceride prepared by the above method.
本发明所要解决的技术问题之三在于提供一种食用安全性高的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂。The third technical problem to be solved by the present invention is to provide a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid which is highly safe to eat.
本发明所要解决的技术问题之四在于提供一种上述含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的制备方法。The fourth technical problem to be solved by the present invention is to provide a method for preparing the above structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
本发明所要解决的技术问题之五在于提供一种含有上述含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的特殊膳食。A fifth technical problem to be solved by the present invention is to provide a special diet containing the above-mentioned structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
技术解决方案Technical solution
为了解决上述技术问题，本发明提供的含有2-棕榈酸甘油酯的组合物的制备方法包括以下步骤：（1）提供含有棕榈酸残基的甘油酯；（2）将含有棕榈酸残基的甘油酯与棕榈酸、棕榈酸盐或棕榈酸非甘油酯混合进行酯交换，得到油脂A；（3）将油脂A与不饱和脂肪酸或其非甘油酯进行Sn-1,3位酶促定向酯交换，得到混合油B；（4）将混合油B精制，得到含有2-棕榈酸甘油酯的组合物。In order to solve the above technical problems, the preparation method of the composition containing 2-palmitic acid glyceride provided by the present invention comprises the steps of: (1) providing a glyceride containing a palmitic acid residue; (2) providing a palmitic acid residue. Glyceride is mixed with palmitic acid, palmitate or palmitic acid non-glyceride for transesterification to obtain oil A; (3) lipid A and unsaturated fatty acid or its non-glyceride are subjected to Sn-1, enzymatically oriented ester at position 3 The mixture was exchanged to obtain a mixed oil B; (4) The mixed oil B was purified to obtain a composition containing 2-palmitic acid glyceride.
优选地，棕榈酸盐包括棕榈酸钠或棕榈酸钾，棕榈酸盐与含有棕榈酸残基的甘油酯的重量比不大于4:1，优选为1:500至4:1，更优选的为1:50至1:1。Preferably, the palmitate comprises sodium palmitate or potassium palmitate, and the weight ratio of palmitate to glyceride containing palmitic acid residues is no more than 4:1, preferably 1:500 to 4:1, more preferably 1:50 to 1:1.
优选地，棕榈酸非甘油酯包括棕榈酸甲酯或棕榈酸乙酯，棕榈酸非甘油酯与含有棕榈酸残基的甘油酯的重量比不大于4:1，优选为1:500至4:1，更优选的为1:50至1:1。Preferably, the palmitic acid non-glyceride comprises methyl palmitate or ethyl palmitate, and the weight ratio of palmitic acid non-glyceride to glyceride containing palmitic acid residues is not more than 4:1, preferably 1:500 to 4: 1, more preferably from 1:50 to 1:1.
优选地，棕榈酸与含有棕榈酸残基的甘油酯的重量比不大于4:1，优选为1:500至4:1，更优选的为1:50至1:1。Preferably, the weight ratio of palmitic acid to glyceride containing palmitic acid residues is no more than 4:1, preferably 1:500 to 4:1, more preferably 1:50 to 1:1.
优选地，步骤（2）的酯交换体系中，进一步加入水，水与含有棕榈酸残基的甘油酯的比重小于5wt%，优选小于2wt%，更优选小于1wt%。Preferably, in the transesterification system of step (2), water is further added, and the specific gravity of water and the glyceride containing palmitic acid residues is less than 5% by weight, preferably less than 2% by weight, more preferably less than 1% by weight.
优选地，步骤（2）的酯交换体系中，选用棕榈酸非甘油酯为反应物时，可加入脂肪酶，脂肪酶与含有棕榈酸残基的甘油酯的比重为1wt%至50wt%。 Preferably, in the transesterification system of the step (2), when non-glycerol palmitate is selected as the reactant, a lipase may be added, and the specific gravity of the lipase and the glyceride containing the palmitic acid residue is 1% by weight to 50% by weight.
优选地，步骤（2）的酯交换结束后，经过精制制得油脂A。Preferably, after the end of the transesterification of the step (2), the oil and fat A is obtained by refining.
优选地，步骤（3）中，油脂A与不饱和脂肪酸或其非甘油酯的重量比为2:1至1:10，优选为1:1至1:3。Preferably, in step (3), the weight ratio of the fat A to the unsaturated fatty acid or its non-glyceride is from 2:1 to 1:10, preferably from 1:1 to 1:3.
优选地，步骤（3）的酶促定向酯交换体系中，进一步加入溶剂，所述溶剂包括己烷、环己烷、辛烷或异辛烷。Preferably, in the enzymatically oriented transesterification system of step (3), a solvent further comprising hexane, cyclohexane, octane or isooctane is further added.
优选地，步骤（3）中的不饱和脂肪酸包括油酸、亚油酸、亚麻酸、花生四烯酸、二十碳五烯酸及二十二碳六烯酸。Preferably, the unsaturated fatty acid in the step (3) includes oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid.
本发明还提供由上述方法制备的含有2-棕榈酸甘油酯的组合物。The present invention also provides a composition containing 2-palmitic acid glyceride prepared by the above method.
本发明提供的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，其中甘油三酯的含量不低于90%，3-氯-1,2-丙二醇与缩水甘油的总含量不高于1.8mg/kg，且3-氯-1,2-丙二醇的含量不高于1.2mg/kg。The structural grease containing 1,3-diunsaturated fatty acid-2-palmitic acid provided by the invention has a triglyceride content of not less than 90%, and the total content of 3-chloro-1,2-propanediol and glycidol is not It is higher than 1.8 mg/kg, and the content of 3-chloro-1,2-propanediol is not more than 1.2 mg/kg.
进一步的，本发明的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，3-氯-1,2-丙二醇与缩水甘油的总含量不高于0.5mg/kg，且3-氯-1,2-丙二醇的含量不高于0.4mg/kg。Further, the structural fat of the 1,3-diunsaturated fatty acid-2-palmitic acid of the present invention, the total content of 3-chloro-1,2-propanediol and glycidol is not more than 0.5 mg/kg, and 3- The content of chloro-1,2-propanediol is not higher than 0.4 mg/kg.
本发明的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，其3-氯-1,2-丙二醇的含量较低，且3-氯-1,2-丙二醇与缩水甘油的总含量处于也较低，因此食用安全性高。The structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid of the present invention has a low content of 3-chloro-1,2-propanediol, and 3-chloro-1,2-propanediol and glycidol The total content is also low, so the food safety is high.
本发明还提供一种制备含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，包括：提供未经过脱臭的含有棕榈酸残基的植物油毛油；将含有棕榈酸残基的植物油毛油与不饱和脂肪酸或其非甘油酯进行Sn-1,3位酶促定向酯交换，得到混合油；将混合油精制，制得含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂。The present invention also provides a method for preparing a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid, comprising: providing a vegetable oil containing a palmitic acid residue which has not been deodorized; and containing a palmitic acid residue The vegetable oil oil and the unsaturated fatty acid or its non-glyceride are subjected to the enzymatic transesterification of the Sn-1, 3 position to obtain a mixed oil; the mixed oil is refined to obtain the 1,3-diunsaturated fatty acid-2-palm Acid structure oil.
本发明还提供含有上述含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的特殊膳食，该特殊膳食为婴儿配方奶粉、婴幼儿配方米粉、儿童牛奶、儿童酸奶及消化功能异常病人的营养膳食。The invention also provides a special diet comprising the above-mentioned structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid, the special diet is infant formula, infant formula rice flour, child milk, children's yogurt and digestive dysfunction patients Nutritional meal.
有益效果Beneficial effect
本发明提出了一种新的含有2-棕榈酸甘油酯组合物的制备方法，其制备工艺简单。与现有方法相比，使用本发明的方法制得的产品中，2位棕榈酸含量更高，且制备后的副产物较少，因此有利于环保。而制备含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法所使用的原材料容易获得，且整个步骤简单，因此能适应大规模的工业化生产的需要。 The invention provides a novel preparation method comprising a 2-palmitic acid glyceride composition, which has a simple preparation process. Compared with the prior art, the product obtained by the method of the present invention has higher palmitic acid content and less by-products after preparation, thereby contributing to environmental protection. The raw material used in the method for preparing a structural fat or oil containing 1,3-di-unsaturated fatty acid-2-palmitic acid is easily available, and the entire step is simple, so that it can be adapted to the needs of large-scale industrial production.
附图说明DRAWINGS
图1是应用含2-棕榈酸甘油酯的组合物制作特殊膳食的配方表。BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a formulation of a special diet prepared using a composition containing 2-palmitic acid glyceride.
图2是应用含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂制作特殊膳食的配方表。Fig. 2 is a formulation table for preparing a special diet using a structural fat containing 1,3-diunsaturated fatty acid-2-palmitic acid.
以下结合附图及实施例对发明作进一步说明。The invention will be further described below in conjunction with the accompanying drawings and embodiments.
本发明的实施方式Embodiments of the invention
以下实施例更详细的说明本发明的微生物油生产及应用方法。The following examples illustrate the production and application of the microbial oil of the present invention in more detail.
实施例1Example 1
(1) 提供一种棕榈油，其棕榈酸占总脂肪酸比例为21.7%，2位棕榈酸含量为15.6%。其中，“2位棕榈酸含量”是指2位上棕榈酸占2位上所有脂肪酸的含量，其检测方法参考GB/T24894，下同。(1) Provided is a palm oil having a ratio of palmitic acid to total fatty acid of 21.7% and a palmitic acid content of 15.6%. Among them, "2 palmitic acid content" refers to the content of all fatty acids in the 2 position of palmitic acid at the 2 position, and the detection method thereof refers to GB/T24894, the same below.
(2) 将反应底物棕榈油25g、棕榈酸1g及氢氧化钾0.5g置于烧瓶中，搅拌升温至170℃并保持恒定，持续反应10小时（酯交换，下同）后，加己烷50mL充分溶解后离心除去脂肪酸钾，得到油脂A。(2) 25 g of the reaction substrate palm oil, 1 g of palmitic acid, and 0.5 g of potassium hydroxide were placed in a flask, stirred and heated to 170 ° C and kept constant, and the reaction was continued for 10 hours (transesterification, the same hereinafter), and then 50 mL of hexane was sufficiently dissolved. After removing the fatty acid potassium by centrifugation, the fat A was obtained.
(3) 将油脂A 20g与油酸20g混合，置于四口烧瓶中，搅拌升温至68℃并保持恒定，加入sn-1,3特异性脂肪酶2.4g，回流反应8小时（定向酯交换，下同），获得混合油B。(3) Will grease A 20g was mixed with 20g of oleic acid, placed in a four-necked flask, stirred and heated to 68 ° C and kept constant, adding 2.4 g of sn-1,3 specific lipase, refluxing for 8 hours (directed transesterification, the same below), obtained Mix oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，干法分馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC（高温毛细管柱，FID检测器，下同）及薄层层析检测2位棕榈酸含量为 20.1wt%。其中，含有2-棕榈酸甘油酯的组合物为含1,3-二油酸-2-棕榈酸的结构油脂。通过检测，该结构油脂中1,3-二油酸-2-棕榈酸的含量为15.4wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.64mg/kg，其中3-氯-1,2-丙二醇的含量为1.03mg/kg。(4) The mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a composition containing 2-palmitic acid glyceride, which is passed through a GC (high temperature capillary column, FID detection). , the same as below) and thin layer chromatography to detect the content of palmitic acid at position 2 20.1 wt%. Among them, the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-dioleic acid-2-palmitic acid. The content of 1,3-dioleic acid-2-palmitic acid in the structural oil was 15.4% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.64 mg/kg, wherein 3- The content of chloro-1,2-propanediol was 1.03 mg/kg.
实施例2Example 2
(1) 提供一种棕榈油，其棕榈酸占总脂肪酸比例为22.8%，2位棕榈酸含量为16.4%。(1) Providing a palm oil having a ratio of palmitic acid to total fatty acid of 22.8% and a palmitic acid content of 16.4%.
(2) 将棕榈油50g、棕榈酸甲酯1g及脂肪酶0.5g加入烧瓶中，搅拌升温至76℃并保持恒定，持续反应8小时。反应结束后，通过干法分馏除去脂肪酸甲酯，得到油脂A。(2) 50 g of palm oil, 1 g of methyl palmitate and 0.5 g of lipase were placed in a flask, and the mixture was heated to 76 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid methyl ester was removed by dry fractionation to obtain a fat or oil A.
(3) 将油脂A 40g与亚油酸20g混合，置于四口烧瓶中，搅拌升温至70℃并保持恒定，加入200mL环己烷，加入sn-1,3特异性脂肪酶2.4g，回流反应7小时，得到混合油B。(3) Will grease A 40g was mixed with 20g of linoleic acid, placed in a four-necked flask, stirred and heated to 70 ° C and kept constant, 200mL of cyclohexane was added, 2.4g of sn-1,3 specific lipase was added, and reflux reaction was carried out for 7 hours to obtain a mixture. Oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，干法分馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为 21.0wt%。其中，含有2-棕榈酸甘油酯组合物为含1,3-二亚油酸-2-棕榈酸的结构油脂。通过检测，该结构油脂中，1,3-二亚油酸-2-棕榈酸的含量为10.9wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.01mg/kg，其中3-氯-1,2-丙二醇的含量为0.68mg/kg。(4) The mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The content of palmitic acid is 21.0 wt%. Among them, the 2-palmitic acid glyceride-containing composition is a structural fat or oil containing 1,3-dilinoleic acid-2-palmitic acid. By detecting, the content of 1,3-dilinoleic acid-2-palmitic acid in the structural oil is 10.9 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 1.01 mg/kg, wherein The content of 3-chloro-1,2-propanediol was 0.68 mg/kg.
实施例3Example 3
在同等条件下，分别按本发明的制备方法与现有的制备方法制备产品，并进行比较。Under the same conditions, the products were prepared according to the preparation method of the present invention and the existing preparation methods, respectively, and compared.
本发明方法Method of the invention
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23.0%，2位棕榈酸含量为16.9%。(1) A shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
(2) 将反应底物起酥油200g、棕榈酸乙酯200g、脂肪酶20g及去离子水1g置于容器中，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，通过分子蒸馏除去脂肪酸乙酯，得到油脂A。(2) 200 g of the reaction substrate shortening, 200 g of ethyl palmitate, 20 g of lipase, and 1 g of deionized water were placed in a container, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
(3) 将油脂A 300g与花生四烯酸600g混合，置于容器中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，维持反应8小时，得到混合油B。(3) Will grease A 300 g of the mixture was mixed with 600 g of arachidonic acid, placed in a container, stirred and heated to 60 ° C and kept constant, 700 mL of octane was added, and 37 g of sn-1,3 specific lipase was added thereto, and the reaction was maintained for 8 hours to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过干法分馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC及薄层层析检测2位棕榈酸含量为 49wt%。其中，含有2-棕榈酸甘油酯的组合物为含1,3-二花生四烯酸-2-棕榈酸的结构油脂。通过检测，该结构油脂1,3-二花生四烯酸-2-棕榈酸的含量为27.9wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.11mg/kg，其中3-氯-1,2-丙二醇的含量为0.74mg/kg。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, by GC and thin layer chromatography. Detection of 2 palmitic acid content is 49wt%. Among them, the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-diarachidonic acid-2-palmitic acid. By testing, the content of the structure oil 1,3-diarachidonic acid-2-palmitic acid was 27.9% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.11 mg/kg, of which 3 The content of -chloro-1,2-propanediol was 0.74 mg/kg.
现有技术方法Prior art method
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23.0%，2位棕榈酸含量为16.9%。(1) A shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
(2) 将反应底物起酥油400g、脂肪酶20g及去离子水1g置于容器中，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，得到油脂A。(2) 400 g of the reaction substrate shortening, 20 g of lipase, and 1 g of deionized water were placed in a container, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After the reaction was completed, the fat A was obtained.
(3) 将油脂A 300g与花生四烯酸600g混合，置于容器中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，维持反应8小时，得到混合油B。(3) Will grease A 300 g of the mixture was mixed with 600 g of arachidonic acid, placed in a container, stirred and heated to 60 ° C and kept constant, 700 mL of octane was added, and 37 g of sn-1,3 specific lipase was added thereto, and the reaction was maintained for 8 hours to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过干法分馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC及薄层层析检测2位棕榈酸含量为 20.1wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, by GC and thin layer chromatography. Detection of 2 palmitic acid content is 20.1 wt%.
通过对比可以看出，本发明在步骤2中添加了棕榈酸乙酯后，终产物中2位棕榈酸含量得到了极大地提高。As can be seen from the comparison, after the addition of ethyl palmitate in the step 2 of the present invention, the palmitic acid content of the final product in the final product is greatly improved.
实施例4Example 4
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23%，2位棕榈酸含量为16.9%。(1) A shortening is provided in which palmitic acid accounts for 23% of total fatty acids and 2 palmitic acid content is 16.9%.
(2) 将反应底物起酥油2000g、棕榈酸乙酯500g及脂肪酶1000g置于容器中，氮气保护下加热至50℃并保持恒定，持续反应5小时。反应结束后，通过分子蒸馏除去脂肪酸乙酯，得到油脂A。(2) The reaction substrate shortening 2000 g, ethyl palmitate 500 g, and lipase 1000 g were placed in a container, heated to 50 ° C under nitrogen atmosphere and kept constant, and the reaction was continued for 5 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
(3) 将油脂A 2000g与花生四烯酸20000g混合置于容器中，搅拌升温至75℃并保持恒定，加入7L己烷，加入sn-1,3特异性脂肪酶500g，安装冷凝回流管，持续反应6小时，得到混合油B。(3) Will grease A 2000g was mixed with 20,000g of arachidonic acid in a container, stirred and heated to 75 ° C and kept constant, 7L of hexane was added, 500g of sn-1,3 specific lipase was added, and a condensation reflux tube was installed to continue the reaction for 6 hours. Mix oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为26.6%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 26.6%.
实施例5Example 5
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为42.4%，2位棕榈酸含量为31.5%。(1) A shortening is provided in which palmitic acid accounts for 42.4% of total fatty acids and 2 palmitic acid content is 31.5%.
(2) 将反应底物棕榈油硬脂精240g、棕榈酸钠24g及去离子水12g置于烧瓶中，氮气保护下加热至190℃并保持恒定，持续反应10小时。反应结束后，加丙酮600mL充分溶解后离心除去脂肪酸钠，得到油脂A。(2) The reaction substrate palm oil stearin 240 g, sodium palmitate 24 g, and deionized water 12 g were placed in a flask, heated to 190 ° C under nitrogen atmosphere and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, 600 mL of acetone was sufficiently dissolved, and then the fatty acid sodium was centrifuged to obtain a fat or oil A.
(3) 将油脂A 200g与二十碳五烯酸600g混合，置于四口烧瓶中，搅拌升温至45℃并保持恒定，加入700mL异辛烷，加入sn-1,3特异性脂肪酶40g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 200g and 600g of eicosapentaenoic acid were mixed, placed in a four-necked flask, stirred and heated to 45 ° C and kept constant, 700 mL of isooctane was added, and 40 g of sn-1,3 specific lipase was added to install a condensing reflux tube. The reaction was maintained for 8 hours to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为40.2wt%。其中，含有2-棕榈酸甘油酯组合物为含1,3-二二十碳五烯酸-2-棕榈酸的结构油脂，通过检测，该结构油脂的1,3-二二十碳五烯酸-2-棕榈酸的含量为24.9wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.55mg/kg，其中3-氯-1,2-丙二醇的含量为1.01mg/kg。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 40.2% by weight. Wherein, the composition containing 2-palmitic acid glyceride is a structural oil containing 1,3-dicosapentaenoic acid-2-palmitic acid, and the 1,3-dicosapentaene of the structural oil is detected by detection. The content of acid-2-palmitic acid was 24.9% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol was 1.55 mg/kg, and the content of 3-chloro-1,2-propanediol was 1.01 mg/ Kg.
实施例6Example 6
在同等条件下，分别按本发明制备方法与现有的制备方法制备产品，并进行比较。Under the same conditions, the products were prepared according to the preparation method of the present invention and the existing preparation methods, and compared.
本发明方法Method of the invention
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为43.7%，2位棕榈酸含量为31.8%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 43.7% and a palmitic acid content of 31.8%.
(2) 将反应底物棕榈油硬脂精2500g、棕榈酸钾500g及去离子水12.5g置于烧瓶中，加入氮气保护，搅拌升温至160℃保持恒定，持续反应30小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 2500 g of the reaction substrate palm oil stearin, 500 g of potassium palmitate and 12.5 g of deionized water were placed in a flask, and nitrogen gas was added thereto, and the mixture was stirred and heated to 160 ° C to be kept constant, and the reaction was continued for 30 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 2500g与二十二碳六烯酸5000g混合，置于容器中，搅拌升温至65℃并保持恒定，加入700mL己烷，加入sn-1,3特异性脂肪酶375g，安装冷凝回流管，维持反应5小时，得到混合油B。(3) Will grease A 2500g and 5000g of docosahexaenoic acid were mixed, placed in a container, stirred and heated to 65 ° C and kept constant, 700 mL of hexane was added, 375 g of sn-1,3 specific lipase was added, and a condensing reflux tube was installed to maintain the reaction. After 5 hours, a mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为45.4wt%。其中，含有2-棕榈酸甘油酯组合物为含1,3-二二十二碳六烯酸-2-棕榈酸的结构油脂，通过检测，该结构油脂的1,3-二二十二碳六烯酸-2-棕榈酸的含量为28.6wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.69mg/kg，其中3-氯-1,2-丙二醇的含量为1.15mg/kg。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 45.4% by weight. Wherein, the composition containing 2-palmitic acid glyceride is a structural fat or oil containing 1,3-didocosahexaenoic acid-2-palmitic acid, and the 1,3-t22 carbon of the structural fat is detected by the detection. The content of hexenoic acid-2-palmitic acid is 28.6% by weight, the total content of 3-chloro-1,2-propanediol and glycidol is 1.69 mg/kg, and the content of 3-chloro-1,2-propanediol is 1.15. Mg/kg.
现有技术方法Prior art method
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为43.7%，2位棕榈酸含量为31.8%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 43.7% and a palmitic acid content of 31.8%.
(2) 将反应底物棕榈油硬脂精3000g、脂肪酶100g及去离子水12.5g置于烧瓶中，加入氮气保护，搅拌升温至160℃保持恒定，持续反应30小时。反应结束后，得到油脂A。(2) The reaction substrate palm oil stearin 3000 g, lipase 100 g, and deionized water 12.5 g were placed in a flask, and nitrogen gas was added thereto, and the mixture was heated to 160 ° C with stirring to keep the reaction constant for 30 hours. After the reaction was completed, the fat A was obtained.
(3) 将油脂A 2500g与二十二碳六烯酸5000g混合，置于容器中，搅拌升温至65℃并保持恒定，加入7000mL己烷，加入sn-1,3特异性脂肪酶375g，安装冷凝回流管，维持反应5小时，得到混合油B。(3) Will grease A 2500g was mixed with 5000g of docosahexaenoic acid, placed in a container, stirred and heated to 65 ° C and kept constant, added 7000mL of hexane, added sn-1,3 specific lipase 375g, installed condensate reflux tube to maintain the reaction After 5 hours, a mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为38.4wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 38.4% by weight.
通过对比可以看出，本发明在步骤2中添加了棕榈酸钾后，终产物中2位棕榈酸含量得到了提高。As can be seen from the comparison, after the addition of potassium palmitate in the step 2 of the present invention, the palmitic acid content of the final product in the final product is improved.
实施例7Example 7
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为61.9%，2位棕榈酸含量为43.9%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 61.9% and a palmitic acid content of 43.9%.
(2) 将反应底物棕榈油硬脂精200g、棕榈酸钠50g及去离子水1.25g置于烧瓶中，搅拌升温至190℃并保持恒定，持续反应10小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 200 g of the reaction substrate palm oil stearin, 50 g of sodium palmitate, and 1.25 g of deionized water were placed in a flask, and the mixture was heated to 190 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 200g与油酸700g混合，置于四口烧瓶中，搅拌升温至50℃并保持恒定，加入70mL己烷，加入sn-1,3特异性脂肪酶50g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 200 g was mixed with 700 g of oleic acid, placed in a four-necked flask, stirred and heated to 50 ° C and kept constant, 70 mL of hexane was added, 50 g of sn-1,3 specific lipase was added, and a condensing reflux tube was installed to maintain the reaction for 8 hours. The mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为63.3wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 63.3 wt%.
实施例8Example 8
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为61.9%，2位棕榈酸含量为43.9%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 61.9% and a palmitic acid content of 43.9%.
(2) 将反应底物棕榈油硬脂精2500g、棕榈酸钠500g及去离子水12.5g置于容器中，搅拌升温至190℃并保持恒定，持续反应10小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 2500 g of the reaction substrate palm oil stearin, 500 g of sodium palmitate, and 12.5 g of deionized water were placed in a container, and the mixture was heated to 190 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 2500g与油酸7500g混合，置于容器中，搅拌升温至50℃并保持恒定，加入7000mL己烷，加入sn-1,3特异性脂肪酶500g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 2500g was mixed with 7500g of oleic acid, placed in a container, stirred and heated to 50 ° C and kept constant, 7000mL of hexane was added, 500g of sn-1,3 specific lipase was added, and a condensation reflux tube was installed to maintain the reaction for 8 hours to obtain a mixture. Oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为62.0wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 62.0% by weight.
实施例9Example 9
在同等条件下，分别按本发明的制备方法与现有的制备方法制备产品，并进行比较。Under the same conditions, the products were prepared according to the preparation method of the present invention and the existing preparation methods, respectively, and compared.
本发明方法Method of the invention
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为64%，2位棕榈酸含量为45.5%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 64% and a palmitic acid content of 45.5%.
(2) 将反应底物棕榈油硬脂精250g、棕榈酸钾83.3g及去离子水1.25g置于容器中，搅拌升温至220℃并保持恒定，持续反应8小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) The reaction substrate palm oil stearin 250 g, potassium palmitate 83.3 g, and deionized water 1.25 g were placed in a container, and the mixture was heated to 220 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 250g与花生四烯酸500g混合，置于容器中，搅拌升温至60℃并保持恒定，加入700mL己烷，加入sn-1,3特异性脂肪酶37.5g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 250g was mixed with 500g of arachidonic acid, placed in a container, stirred and heated to 60 ° C and kept constant, 700mL of hexane was added, 37.5g of sn-1,3 specific lipase was added, and a condensation reflux tube was installed to maintain the reaction for 8 hours. , to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为68.2wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 68.2% by weight.
现有技术方法Prior art method
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为64%，2位棕榈酸含量为45.5%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 64% and a palmitic acid content of 45.5%.
(2) 将反应底物棕榈油硬脂精333.3g、脂肪酶10g及去离子水1.25g置于容器中，搅拌升温至220℃并保持恒定，持续反应8小时。反应结束后，得到油脂A。(2) 333.3 g of the reaction substrate palm oil stearin, 10 g of lipase, and 1.25 g of deionized water were placed in a container, and the mixture was heated to 220 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After the reaction was completed, the fat A was obtained.
(3) 将油脂A 250g与花生四烯酸500g混合，置于容器中，搅拌升温至60℃并保持恒定，加入700mL己烷，加入sn-1,3特异性脂肪酶37.5g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 250g was mixed with 500g of arachidonic acid, placed in a container, stirred and heated to 60 ° C and kept constant, 700mL of hexane was added, 37.5g of sn-1,3 specific lipase was added, and a condensation reflux tube was installed to maintain the reaction for 8 hours. , to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为56.5wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 56.5 wt%.
通过对比可以看出，本发明在步骤2中添加了棕榈酸钾后，终产物中2位棕榈酸含量得到了提高。As can be seen from the comparison, after the addition of potassium palmitate in the step 2 of the present invention, the palmitic acid content of the final product in the final product is improved.
实施例10Example 10
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为62.3%，2位棕榈酸含量为44.4%。(1) A palm oil stearin is provided, which has a ratio of palmitic acid to total fatty acid of 62.3% and a palmitic acid content of 44.4%.
(2) 将反应底物棕榈油硬脂精250g、棕榈酸钾15g及去离子水1.25g置于容器中，搅拌升温至160℃并保持恒定，持续反应10小时。反应结束后，加己烷600mL充分溶解，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 250 g of the reaction substrate palm oil stearin, 15 g of potassium palmitate and 1.25 g of deionized water were placed in a container, stirred and heated to 160 ° C and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, 600 mL of hexane was sufficiently dissolved, and the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat and oil A.
(3) 将油脂A 200g与油酸1200g混合，置于容器中，搅拌升温至70℃并保持恒定，加入sn-1,3特异性脂肪酶70g，安装冷凝回流管，维持反应6小时，得到混合油B。(3) Will grease A 200 g of the mixture was mixed with 1200 g of oleic acid, placed in a container, stirred and heated to 70 ° C and kept constant, and 70 g of a sn-1,3 specific lipase was added thereto, and a condensation reflux tube was installed to maintain the reaction for 6 hours to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为58.1wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 58.1% by weight.
实施例11Example 11
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为64%，2位棕榈酸含量为45.5%。(1) Providing a palm oil stearin having a ratio of palmitic acid to total fatty acid of 64% and a palmitic acid content of 45.5%.
(2) 将反应底物棕榈油硬脂精5000g、棕榈酸钾150g及去离子水12g置于容器中，搅拌升温至220℃并保持恒定，持续反应8小时。反应结束后，加丙酮16L充分溶解，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) The reaction substrate palm oil stearin 5000 g, potassium palmitate 150 g, and deionized water 12 g were placed in a container, stirred and heated to 220 ° C and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, 16 L of acetone was sufficiently dissolved, and the soap was removed by centrifugal filtration (the content of the soap was less than 10 ppm) to obtain a fat and oil A.
(3) 将油脂A 3000g与亚麻酸6000g混合，置于容器中，搅拌升温至60℃并保持恒定，加入7000mL己烷，加入sn-1,3特异性脂肪酶400g，安装冷凝回流管，维持反应4小时，得到混合油B。(3) Will grease A 3000g mixed with 6000g of linolenic acid, placed in a container, stirred and heated to 60 ° C and kept constant, add 7000mL of hexane, add 400g of sn-1,3 specific lipase, install condensate reflux tube, maintain the reaction for 4 hours, get mixed Oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为59.2wt%。其中，含有2-棕榈酸甘油酯组合物为含1,3-二亚麻酸-2-棕榈酸的结构油脂，通过检测，其1,3-二亚麻酸-2-棕榈酸的含量为34.4wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为1.76mg/kg，其中3-氯-1,2-丙二醇的含量为1.10mg/kg。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 59.2% by weight. Wherein, the composition containing 2-palmitic acid glyceride is a structural oil containing 1,3-dilinolenic acid-2-palmitic acid, and the content of 1,3-dilinolenic acid-2-palmitic acid is 34.4wt by detection. The total content of %, 3-chloro-1,2-propanediol and glycidol was 1.76 mg/kg, and the content of 3-chloro-1,2-propanediol was 1.10 mg/kg.
实施例12Example 12
(1) 提供一种棕榈油硬脂精，其棕榈酸占总脂肪酸比例为71.5%，2位棕榈酸含量为55.6%。(1) Provided is a palm oil stearin having a ratio of palmitic acid to total fatty acid of 71.5% and a palmitic acid content of 55.6%.
(2) 将反应底物棕榈油硬脂精10000g、棕榈酸钠20g及去离子水12g置于容器中，搅拌升温至160℃并保持恒定，持续反应10小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) The reaction substrate palm oil stearin 10000 g, sodium palmitate 20 g, and deionized water 12 g were placed in a container, and the mixture was heated to 160 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 5000g与亚油酸乙酯30000g混合，置于容器中，搅拌升温至68℃并保持恒定，加入7000mL己烷，加入sn-1,3特异性脂肪酶4000g，安装冷凝回流管，维持反应9小时，得到混合油B。(3) Will grease A 5000g was mixed with 30,000 parts of ethyl linoleate, placed in a container, stirred and heated to 68 ° C and kept constant, 7000 mL of hexane was added, 4000 g of sn-1,3 specific lipase was added, and a condensation reflux tube was installed to maintain the reaction for 9 hours. , to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去脂肪酸乙酯，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为63.1wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the fatty acid ethyl ester by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content at the 2 position was 63.1% by weight.
实施例13Example 13
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为16.5%,，2位棕榈酸含量为13.3%。(1) A shortening is provided, in which palmitic acid accounts for 16.5% of total fatty acids, and 2 palmitic acid content is 13.3%.
(2) 将反应底物起酥油250g、棕榈酸钠50g及去离子水1.25g置于烧瓶中，加入氦气保护，搅拌升温至150℃并保持恒定，持续反应20小时。反应结束后，加入丙酮700mL，充分溶解后离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 250 g of the reaction substrate shortening, 50 g of sodium palmitate and 1.25 g of deionized water were placed in a flask, and helium gas was added thereto, and the mixture was heated to 150 ° C with stirring and kept constant, and the reaction was continued for 20 hours. After completion of the reaction, 700 mL of acetone was added thereto, and the mixture was sufficiently dissolved, and then the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat and oil A.
(3) 将油脂A 250g与油酸500g混合，置于四口烧瓶中，搅拌升温至72℃并保持恒定，加入700mL己烷，加入sn-1,3特异性脂肪酶37.5g，安装冷凝回流管，维持反应12小时，得到混合油B。(3) Will grease A 250 g mixed with 500 g of oleic acid, placed in a four-necked flask, stirred and heated to 72 ° C and kept constant, added 700 mL of hexane, added 37.5 g of sn-1,3 specific lipase, and installed a condensing reflux tube to maintain the reaction for 12 hours. , to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯组合物，通过GC及薄层层析检测2位上棕榈酸含量为21.1wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain the composition containing the 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content was 21.1% by weight.
实施例14Example 14
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23.0%，2位棕榈酸含量为16.9%(1) Providing a shortening with palmitic acid as a percentage of total fatty acids of 23.0% and a palmitic acid content of 16.9%.
(2) 将反应底物起酥油200g、棕榈酸乙酯400g、脂肪酶10g及去离子水1g置于烧瓶中，加入氦气保护，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，分子蒸馏法除去脂肪酸乙酯，得到油脂A。(2) 200 g of the reaction substrate shortening, 400 g of palmitate, 10 g of lipase, and 1 g of deionized water were placed in a flask, and helium gas was added thereto, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
(3) 将油脂A 300g与花生四烯酸600g混合，置于四口烧瓶中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 300g was mixed with 600g of arachidonic acid, placed in a four-necked flask, stirred and heated to 60 ° C and kept constant, 700mL of octane was added, and 37g of sn-1,3 specific lipase was added to install a condensing reflux tube to maintain the reaction 8 In hours, mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC及薄层层析检测2位上棕榈酸含量为50.8wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content at the 2-position was 50.8 wt%.
实施例15Example 15
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23.0%，2位棕榈酸含量为16.9%。(1) A shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
(2) 将反应底物起酥油200g、棕榈酸乙酯600g、脂肪酶10g及去离子水1g置于烧瓶中，加入氦气保护，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，分子蒸馏法除去脂肪酸乙酯，得到油脂A。(2) 200 g of the reaction substrate shortening, 600 g of ethyl palmitate, 10 g of lipase, and 1 g of deionized water were placed in a flask, and helium gas was added thereto, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
(3) 将油脂A 300g与花生四烯酸600g混合，置于四口烧瓶中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 300g was mixed with 600g of arachidonic acid, placed in a four-necked flask, stirred and heated to 60 ° C and kept constant, 700mL of octane was added, and 37g of sn-1,3 specific lipase was added to install a condensing reflux tube to maintain the reaction 8 In hours, mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC及薄层层析检测2位上棕榈酸含量为52.6wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content at the 2-position was 52.6 wt%.
实施例16Example 16
(1) 提供一种起酥油，其棕榈酸占总脂肪酸比例为23.0%，2位棕榈酸含量为16.9%。(1) A shortening is provided in which palmitic acid accounts for 23.0% of total fatty acids and 2 palmitic acid content is 16.9%.
(2) 将反应底物起酥油200g、棕榈酸乙酯800g、脂肪酶10g及去离子水1g置于烧瓶中，加入氦气保护，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，分子蒸馏法除去脂肪酸乙酯，得到油脂A。(2) 200 g of the reaction substrate shortening, 800 g of palmitate, 10 g of lipase, and 1 g of deionized water were placed in a flask, and helium gas was added thereto, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A.
(3) 将油脂A 300g与花生四烯酸600g混合，置于四口烧瓶中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 300g was mixed with 600g of arachidonic acid, placed in a four-necked flask, stirred and heated to 60 ° C and kept constant, 700mL of octane was added, and 37g of sn-1,3 specific lipase was added to install a condensing reflux tube to maintain the reaction 8 In hours, mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过分子蒸馏除去游离脂肪酸，脱臭后即得到含有2-棕榈酸甘油酯的组合物，通过GC及薄层层析检测2位上棕榈酸含量为63.3wt%。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by molecular distillation, and deodorizing to obtain a composition containing 2-palmitic acid glyceride, which is detected by GC and thin layer chromatography. The palmitic acid content at the 2 position was 63.3 wt%.
实施例17Example 17
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为22.1%，2位棕榈酸含量为14.6%。(1) Provided is an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 22.1% and a palmitic acid content of 14.6%.
(2) 将反应底物棕榈毛油25g与亚油酸25g混合，置于容器中，搅拌升温至60℃并保持恒定，加入sn-1,3特异性脂肪酶3g，安装冷凝回流管，维持反应8小时，得到混合油。(2) 25 g of the reaction substrate palm oil and 25 g of linoleic acid were mixed, placed in a container, stirred and heated to 60 ° C and kept constant, and 3 g of a specific lipase of sn-1,3 was added, and a condensation reflux tube was installed to maintain the reaction for 8 hours. , get a mixed oil.
(3) 将混合油纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，干法分馏除去游离脂肪酸，脱臭后即得到含1,3-二亚油酸-2-棕榈酸的结构油脂，通过检测，其1,3-二亚油酸-2-棕榈酸的含量为6.8wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.28mg/kg，其中3-氯-1,2-丙二醇的含量为0.18mg/kg。(3) The mixed oil is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and performing dry fractionation to remove the free fatty acid, and deodorizing to obtain a structural oil containing 1,3-dilinoleic acid-2-palmitic acid, and detecting, The content of 1,3-dilinoleic acid-2-palmitic acid is 6.8 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.28 mg/kg, wherein 3-chloro-1,2 The content of propylene glycol was 0.18 mg/kg.
实施例18Example 18
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为23.7%，2位棕榈酸含量为14.9%。(1) Provided is an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 23.7% and a palmitic acid content of 14.9%.
(2) 将反应底物棕榈毛油200g、棕榈酸乙酯200g、脂肪酶10g及去离子水1g置于容器中，搅拌升温至60℃并保持恒定，持续反应8小时。反应结束后，通过分子蒸馏除去脂肪酸乙酯，得到油脂A。此步骤即为对毛油进行随机酯交换的步骤，其目的是增加中间产物的2位棕榈酸含量，最终增加终产物的2位棕榈酸含量。(2) 200 g of the reaction substrate palm oil, 200 g of palmitate, 10 g of lipase, and 1 g of deionized water were placed in a container, and the mixture was heated to 60 ° C with stirring and kept constant, and the reaction was continued for 8 hours. After completion of the reaction, the fatty acid ethyl ester was removed by molecular distillation to obtain a fat or oil A. This step is a step of random transesterification of the hair oil, the purpose of which is to increase the palmitic acid content of the intermediate product at the 2 position, and finally increase the palmitic acid content of the final product.
(3) 将油脂A 300g与花生四烯酸600g混合，置于容器中，搅拌升温至60℃并保持恒定，加入700mL辛烷，加入sn-1,3特异性脂肪酶37g，维持反应8小时，得到混合油B。(3) Will grease A 300 g of the mixture was mixed with 600 g of arachidonic acid, placed in a container, stirred and heated to 60 ° C and kept constant, 700 mL of octane was added, and 37 g of sn-1,3 specific lipase was added thereto, and the reaction was maintained for 8 hours to obtain a mixed oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，再通过干法分馏除去游离脂肪酸，脱臭后即得到含1,3-二花生四烯酸-2-棕榈酸的结构油脂。通过检测，其1,3-二花生四烯酸-2-棕榈酸的含量为13.7wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.24mg/kg，其中3-氯-1,2-丙二醇的含量为0.16mg/kg。(4) The mixed oil B is purified, and the purification step includes, but is not limited to, filtering and removing the lipase, and then removing the free fatty acid by dry fractionation, and deodorizing to obtain a structural fat containing 1,3-diarachidonic acid-2-palmitic acid. . By testing, the content of 1,3-dirachidotetraenoic acid-2-palmitic acid is 13.7% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.24 mg/kg, wherein 3-chloro The content of -1,2-propanediol was 0.16 mg/kg.
实施例19Example 19
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为40.4%，2位棕榈酸含量为29.5%。(1) An undeodorized palm oil is provided, which has a palmitic acid ratio of 40.4% of total fatty acids and a palmitic acid content of 29.5%.
(2) 将反应底物棕榈毛油240g、棕榈酸钠240g及去离子水12g置于容器中，搅拌升温至190℃并保持恒定，持续反应10小时。反应结束后，加丙酮600mL充分溶解，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 240 g of the reaction substrate palm oil, 240 g of sodium palmitate, and 12 g of deionized water were placed in a container, and the mixture was heated to 190 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, 600 mL of acetone was sufficiently dissolved, and the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat and oil A.
(3) 将油脂A 250g与二十碳五烯酸750g混合，置于容器中，搅拌升温至45℃并保持恒定，加入700mL异辛烷，加入sn-1,3特异性脂肪酶50g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 250g and 750g of eicosapentaenoic acid were mixed, placed in a container, stirred and heated to 45 ° C and kept constant, 700 mL of isooctane was added, 50 g of sn-1,3 specific lipase was added, and a condensing reflux tube was installed to maintain the reaction. After 8 hours, a mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，干法分馏除去游离脂肪酸，脱臭后即得到含1,3-二二十碳五烯酸-2-棕榈酸的结构油脂，通过检测，其1,3-二二十碳五烯酸-2-棕榈酸的含量为23.8wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.49mg/kg，其中3-氯-1,2-丙二醇的含量为0.35mg/kg 。(4) The mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, dry fractionation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dicosapentaenoic acid-2-palmitic acid. By detection, the content of 1,3-docosapentaenoic acid-2-palmitic acid is 23.8 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.49 mg/kg, wherein The content of 3-chloro-1,2-propanediol is 0.35 mg/kg. .
实施例20Example 20
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为45.7%，2位棕榈酸含量为33.8%。(1) Provided is an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 45.7% and a palmitic acid content of 33.8%.
(2) 将反应底物棕榈毛油2500g、棕榈酸钾5000g及去离子水12.5g置于容器中，搅拌升温至160℃并保持恒定，持续反应30小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 2500 g of the reaction substrate palm oil, 5000 g of potassium palmitate and 12.5 g of deionized water were placed in a container, and the mixture was heated to 160 ° C with stirring and kept constant, and the reaction was continued for 30 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 2500g与二十二碳六烯酸5000g混合，置于容器中，搅拌升温至65℃并保持恒定，加入7000mL己烷，加入sn-1,3特异性脂肪酶375g，安装冷凝回流管，维持反应5小时，得到混合油B。(3) Will grease A 2500g was mixed with 5000g of docosahexaenoic acid, placed in a container, stirred and heated to 65 ° C and kept constant, added 7000mL of hexane, added sn-1,3 specific lipase 375g, installed condensate reflux tube to maintain the reaction After 5 hours, a mixed oil B was obtained.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，分子蒸馏除去游离脂肪酸，脱臭后即得到含1,3-二二十二碳六烯酸-2-棕榈酸的结构油脂，通过检测，其1,3-二二十二碳六烯酸-2-棕榈酸的含量为29.7wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.4mg/kg，其中3-氯-1,2-丙二醇的含量为0.29mg/kg。(4) The mixed oil B is purified, and the purification steps include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dopencosyl-2-enoic acid-2-palmitic acid By detection, the content of 1,3-docosahexaenoic acid-2-palmitic acid is 29.7% by weight, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.4 mg/kg. The content of 3-chloro-1,2-propanediol was 0.29 mg/kg.
实施例21Example 21
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为75.7%，2位棕榈酸含量为60.3%。(1) Provided is an undeodorized palm oil having a ratio of palmitic acid to total fatty acid of 75.7% and a palmitic acid content of 60.3%.
(2) 将反应底物棕榈毛油200g、棕榈酸钾600g及去离子水1.25g置于容器中，搅拌升温至190℃并保持恒定，持续反应10小时。反应结束后，离心过滤除去皂（皂的含量小于10ppm），得到油脂A。(2) 200 g of the reaction substrate palm oil, 600 g of potassium palmitate, and 1.25 g of deionized water were placed in a container, and the mixture was heated to 190 ° C with stirring and kept constant, and the reaction was continued for 10 hours. After completion of the reaction, the soap was removed by centrifugation (the content of the soap was less than 10 ppm) to obtain a fat A.
(3) 将油脂A 200g与亚麻酸700g混合，置于容器中，搅拌升温至50℃并保持恒定，加入700mL己烷，加入sn-1,3特异性脂肪酶50g，安装冷凝回流管，维持反应8小时，得到混合油B。(3) Will grease A 200g mixed with 700g of linolenic acid, placed in a container, stirred and heated to 50 ° C and kept constant, add 700mL of hexane, add 50g of sn-1,3 specific lipase, install condensate reflux tube, maintain the reaction for 8 hours, get mixed Oil B.
(4) 将混合油B纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，分子蒸馏除去游离脂肪酸，脱臭后即得到含1,3-二亚麻酸-2-棕榈酸的结构油脂，通过检测，其1,3-二亚麻酸-2-棕榈酸的含量为61.5wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.44mg/kg，其中3-氯-1,2-丙二醇的含量为0.32mg/kg 。(4) The mixed oil B is purified, and the steps of purification include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural fat containing 1,3-dilinolenic acid-2-palmitic acid, which is detected. The content of 1,3-dilinolenic acid-2-palmitic acid is 61.5 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.44 mg/kg, wherein 3-chloro-1,2-propanediol The content is 0.32mg/kg .
实施例22Example 22
(1) 提供一种未经脱臭的棕榈毛油，其棕榈酸占总脂肪酸比例为62.9%，2位棕榈酸含量为44.9%。(1) An undeodorized palm oil is provided, which has a ratio of palmitic acid to total fatty acid of 62.9% and a palmitic acid content of 44.9%.
(2) 将反应底物棕榈毛油2500g与油酸7500g混合，置于容器中，搅拌升温至50℃并保持恒定，加入sn-1,3特异性脂肪酶500g，安装冷凝回流管，维持反应8小时，得到混合油。(2) 2500 g of the reaction substrate palm oil and 7500 g of oleic acid were mixed, placed in a container, stirred and heated to 50 ° C and kept constant, and 500 g of sn-1,3 specific lipase was added thereto, and a condensation reflux tube was installed to maintain the reaction for 8 hours. A mixed oil is obtained.
(3) 将混合油纯化，纯化的步骤包括但不限于：过滤除去脂肪酶，分子蒸馏除去游离脂肪酸，脱臭后即得到含1,3-二油酸-2-棕榈酸的结构油脂，通过检测，其1,3-二油酸-2-棕榈酸的含量为32.3wt%，3-氯-1,2-丙二醇与缩水甘油的总含量为0.15mg/kg，其中3-氯-1,2-丙二醇的含量为0.10mg/kg。(3) The mixed oil is purified, and the steps of purification include, but are not limited to, filtration to remove lipase, molecular distillation to remove free fatty acids, and deodorization to obtain a structural oil containing 1,3-dioleic acid-2-palmitic acid, which is detected by 1 , the content of 3-dioleic acid-2-palmitic acid is 32.3 wt%, and the total content of 3-chloro-1,2-propanediol and glycidol is 0.15 mg/kg, wherein 3-chloro-1,2-propanediol The content is 0.10 mg/kg.
本发明制备含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，步骤简单，有确实可靠的可行性，能适应大规模的工业化生产的需要。进一步的，通过本发明方法所制得的结构油脂，3-氯-1,2-丙二醇与缩水甘油的含量都非常低，因此食用更安全。The method for preparing the structural fat and oil containing the 1,3-diunsaturated fatty acid-2-palmitic acid has the advantages of simple steps, reliable and feasible, and can meet the needs of large-scale industrial production. Further, the structural oil obtained by the method of the present invention has a very low content of 3-chloro-1,2-propanediol and glycidol, so that it is safer to eat.
工业实用性Industrial applicability
含有2-棕榈酸甘油酯的组合物的应用Application of a composition containing 2-palmitic acid glyceride
上述方法制得的含有2-棕榈酸甘油酯的组合物可用于婴儿配方奶粉、婴幼儿配方米粉、儿童牛奶、儿童酸奶及消化功能异常病人的特殊膳食等领域，以下仅以消化功能异常病人的特殊膳食为例，详细介绍本发明的含有2-棕榈酸甘油酯的组合物的应用。The composition containing 2-palmitic acid glyceride prepared by the above method can be used in the fields of infant formula, infant formula rice powder, child milk, children's yogurt and special diet for patients with digestive dysfunction, and the following only for patients with digestive dysfunction The use of a composition containing a 2-palmitic acid glyceride of the present invention is described in detail by taking a special diet as an example.
使用上述实施例5制得的含有2-棕榈酸甘油酯的组合物，按图1所示的配方进行配比。先将大米粉碎，得到大约100至120目的米粉。按照上述配方，配制45%固形物的料浆，5000rpm转速剪切25min后，在20MPa下进行均质，得到均质后的料浆。然后加入0.8%的淀粉酶水解4hr，然后在85℃下糊化45min。糊化好的料浆按照以下参数进行蒸汽辊筒干燥：蒸汽压力为0.45MPa，滚筒转速为4rpm，薄膜厚度为2.5mm。通过以上操作最终可以得到水分含量3%左右的、含有2-棕榈酸甘油酯的特殊膳食米粉。The composition containing 2-palmitic acid glyceride prepared in the above Example 5 was formulated in accordance with the formulation shown in Fig. 1. The rice is first pulverized to obtain about 100 to 120 mesh rice flour. According to the above formula, a slurry of 45% solid matter was prepared, and after shearing at 5000 rpm for 25 minutes, it was homogenized at 20 MPa to obtain a homogenized slurry. It was then hydrolyzed with 0.8% amylase for 4 hr and then gelatinized at 85 ° C for 45 min. The gelatinized slurry was subjected to steam drum drying according to the following parameters: a steam pressure of 0.45 MPa, a drum rotation speed of 4 rpm, and a film thickness of 2.5 mm. Through the above operation, a special dietary rice powder containing 2-palmitic acid glyceride having a moisture content of about 3% can be finally obtained.
制备特殊膳食Preparing special meals
上述制得的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂可用于婴儿配方奶粉、婴幼儿配方米粉、儿童牛奶、儿童酸奶及消化功能异常病人的营养膳食等领域，以下仅以消化功能异常病人的营养膳食为例，详细介绍本发明的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的应用。The above-mentioned structural oil containing 1,3-diunsaturated fatty acid-2-palmitic acid can be used in the fields of infant formula, infant formula rice flour, child milk, children's yogurt and nutritional diet of patients with digestive dysfunction, etc. The nutrient diet of a patient with digestive dysfunction is taken as an example to describe in detail the application of the 1,3-diunsaturated fatty acid-2-palmitic acid-containing structural oil of the present invention.
使用上述任一实施例制得的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，按如图2所示的配方进行配比。先将大米粉碎，得到大约100至120目的米粉。按照上述配方，配制45%固形物的料浆，5000rpm转速剪切25min后，在20MPa下进行均质，得到均质后的料浆。然后加入0.8%的淀粉酶水解4hr，然后在85℃下糊化45min。糊化好的料浆按照以下参数进行蒸汽辊筒干燥：蒸汽压力为0.45MPa，滚筒转速为4rpm，薄膜厚度为2.5mm。The structural grease containing 1,3-diunsaturated fatty acid-2-palmitic acid obtained by using any of the above examples was formulated according to the formulation shown in FIG. The rice is first pulverized to obtain about 100 to 120 mesh rice flour. According to the above formula, a slurry of 45% solid matter was prepared, and after shearing at 5000 rpm for 25 minutes, it was homogenized at 20 MPa to obtain a homogenized slurry. It was then hydrolyzed with 0.8% amylase for 4 hr and then gelatinized at 85 ° C for 45 min. The gelatinized slurry was subjected to steam drum drying according to the following parameters: a steam pressure of 0.45 MPa, a drum rotation speed of 4 rpm, and a film thickness of 2.5 mm.
通过以上操作最终可以得到水分含量3%左右的、含结构油脂的营养膳食米粉。Through the above operation, a nutritious dietary rice flour containing structural oil and fat with a moisture content of about 3% can be finally obtained.

Claims (28)

  1. 含有2-棕榈酸甘油酯的组合物的制备方法，包括如下步骤： A method for preparing a composition containing 2-palmitic acid glyceride, comprising the steps of:
    (1)提供含有棕榈酸残基的甘油酯；(1) providing a glyceride containing a palmitic acid residue;
    (2)将含有棕榈酸残基的甘油酯与棕榈酸、棕榈酸盐或棕榈酸非甘油酯混合进行酯交换，得到油脂A；(2) a glyceride containing a palmitic acid residue is mixed with palmitic acid, palmitate or palmitic acid non-glyceride for transesterification to obtain a fat A;
    (3)将油脂A与不饱和脂肪酸或其非甘油酯进行Sn-1,3位酶促定向酯交换，得到混合油B；(3) the fat A and the unsaturated fatty acid or its non-glyceride are Sn-1, 3 enzymatically oriented transesterification to obtain a mixed oil B;
    (4)将混合油B精制，得到含有2-棕榈酸甘油酯的组合物。(4) The mixed oil B is purified to obtain a composition containing 2-palmitic acid glyceride.
  2. 根据权利要求1所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：所述棕榈酸盐包括棕榈酸钠或棕榈酸钾，棕榈酸盐与含有棕榈酸残基的甘油酯的重量比不大于4:1。 The method for preparing a composition containing 2-palmitic acid glyceride according to claim 1, wherein the palmitate comprises sodium palmitate or potassium palmitate, palmitate and glycerin containing palmitic acid residues. The weight ratio of the ester is not more than 4:1.
  3. 根据权利要求2所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸盐与含有棕榈酸残基的甘油酯的重量比为1:500至4:1。 The method for producing a composition containing 2-palmitic acid glyceride according to claim 2, wherein the weight ratio of palmitate to glyceride containing palmitic acid residues is from 1:500 to 4:1.
  4. 根据权利要求2所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸盐与含有棕榈酸残基的甘油酯的重量比为1:50至1:1。 The method for producing a composition comprising 2-palmitic acid glyceride according to claim 2, wherein the weight ratio of palmitate to glyceride containing palmitic acid residues is from 1:50 to 1:1.
  5. 根据权利要求1所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：所述棕榈酸非甘油酯包括棕榈酸甲酯或棕榈酸乙酯，棕榈酸非甘油酯与含有棕榈酸残基的甘油酯的重量比不大于4:1。 The method for preparing a composition containing 2-palmitic acid glyceride according to claim 1, wherein the non-glyceryl palmitate comprises methyl palmitate or ethyl palmitate, non-glyceryl palmitate and The weight ratio of the glyceride of the palmitic acid residue is not more than 4:1.
  6. 根据权利要求5所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸非甘油酯与含有棕榈酸残基的甘油酯的重量比为1:500至4:1。 The method for preparing a composition containing 2-palmitic acid glyceride according to claim 5, wherein the weight ratio of the non-glycerol palmitate to the glyceride containing the palmitic acid residue is 1:500 to 4:1. .
  7. 根据权利要求5所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸非甘油酯与含有棕榈酸残基的甘油酯的重量比为1:50至1:1。 The method for preparing a composition containing 2-palmitic acid glyceride according to claim 5, wherein the weight ratio of the non-glycerol palmitate to the glyceride containing the palmitic acid residue is 1:50 to 1:1. .
  8. 根据权利要求1所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸与含有棕榈酸残基的甘油酯的重量比不大于4:1。 The method for producing a composition comprising 2-palmitic acid glyceride according to claim 1, wherein the weight ratio of palmitic acid to glyceride containing palmitic acid residues is not more than 4:1.
  9. 根据权利要求8所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸与含有棕榈酸残基的甘油酯的重量比为1:500至4:1。 The method for producing a composition containing 2-palmitic acid glyceride according to claim 8, wherein the weight ratio of palmitic acid to glyceride containing a palmitic acid residue is from 1:500 to 4:1.
  10. 根据权利要求8所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：棕榈酸与含有棕榈酸残基的甘油酯的重量比为1:50至1:1。The method for producing a composition containing 2-palmitic acid glyceride according to claim 8, wherein the weight ratio of palmitic acid to glyceride containing a palmitic acid residue is from 1:50 to 1:1.
  11. 根据权利要求1至10任一项所述的含有2-棕榈酸甘油酯组合物的制备方法，其特征在于：步骤（2）的酯交换体系中，进一步加入水，水与含有棕榈酸残基的甘油酯的比重小于5wt%。The method for preparing a composition containing 2-palmitic acid glyceride according to any one of claims 1 to 10, characterized in that in the transesterification system of the step (2), water, water and a palmitic acid residue are further added. The glyceride has a specific gravity of less than 5% by weight.
  12. 根据权利要求11所述的含有2-棕榈酸甘油酯组合物的制备方法，其特征在于：水与含有棕榈酸残基的甘油酯的比重小于2wt%。The method for producing a composition containing a 2-palmitic acid glyceride according to claim 11, wherein the specific gravity of water and the glyceride having a palmitic acid residue is less than 2% by weight.
  13. 根据权利要求11所述的含有2-棕榈酸甘油酯组合物的制备方法，其特征在于：水与含有棕榈酸残基的甘油酯的比重小于1wt%。The method for producing a composition containing a 2-palmitic acid glyceride according to claim 11, wherein the specific gravity of water and the glyceride having a palmitic acid residue is less than 1% by weight.
  14. 根据权利要求11所述的含有2-棕榈酸甘油酯组合物的制备方法，其特征在于：步骤（2）的酯交换结束后，经过精制制得油脂A。The method for producing a composition containing a 2-palmitic acid glyceride according to claim 11, wherein after the transesterification of the step (2) is completed, the oil and fat A is obtained by purification.
  15. 根据权利要求14所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：步骤（3）中，油脂A与不饱和脂肪酸或其非甘油酯的重量比为2:1至1:10。The method for preparing a composition containing 2-palmitic acid glyceride according to claim 14, wherein in the step (3), the weight ratio of the oil A to the unsaturated fatty acid or the non-glyceride thereof is 2:1 to 1:10.
  16. 根据权利要求15所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：油脂A与不饱和脂肪酸或其非甘油酯的重量比为1:1至1:3。 The method for producing a composition containing 2-palmitic acid glyceride according to claim 15, wherein the weight ratio of the oil A to the unsaturated fatty acid or the non-glyceride thereof is from 1:1 to 1:3.
  17. 根据权利要求16所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：步骤（3）的酶促定向酯交换体系中，进一步加入溶剂，所述溶剂包括己烷、环己烷、辛烷或异辛烷。The method for preparing a composition containing 2-palmitic acid glyceride according to claim 16, wherein in the enzymatically oriented transesterification system of the step (3), a solvent further comprising a hexane or a ring is further added. Hexane, octane or isooctane.
  18. 根据权利要求17所述的含有2-棕榈酸甘油酯的组合物的制备方法，其特征在于：所述不饱和脂肪酸包括油酸、亚油酸、亚麻酸、花生四烯酸、二十碳五烯酸及二十二碳六烯酸。The method for preparing a composition containing 2-palmitic acid glyceride according to claim 17, wherein the unsaturated fatty acid comprises oleic acid, linoleic acid, linolenic acid, arachidonic acid, and twenty carbon five. Oleic acid and docosahexaenoic acid.
  19. 一种含有2-棕榈酸甘油酯的组合物，其特征在于：所述含有2-棕榈酸甘油酯的组合物是按照权利要求1至18中任一项的制备方法所制得。 A composition containing 2-palmitic acid glyceride, characterized in that the composition containing 2-palmitic acid glyceride is obtained by the production method according to any one of claims 1 to 18.
  20. 含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，所述结构油脂中甘油三酯的含量不低于90%，其特征在于：所述结构油脂中，3-氯-1,2-丙二醇与缩水甘油的总含量不高于1.8mg/kg，且3-氯-1,2-丙二醇的含量不高于1.2mg/kg。a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid, wherein the structural fat or oil has a triglyceride content of not less than 90%, and is characterized in that: 3-chloro-1, The total content of 2-propanediol and glycidol is not higher than 1.8 mg/kg, and the content of 3-chloro-1,2-propanediol is not higher than 1.2 mg/kg.
  21. 根据权利要求20所述的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，其特征在于：3-氯-1,2-丙二醇与缩水甘油的总含量不高于0.5mg/kg，且3-氯-1,2-丙二醇的含量不高于0.4mg/kg。The structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 20, wherein the total content of 3-chloro-1,2-propanediol and glycidol is not more than 0.5 mg/ Kg, and the content of 3-chloro-1,2-propanediol is not higher than 0.4 mg/kg.
  22. 根据权利要求20所述的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂，其特征在于：所述不饱和脂肪酸包括油酸、亚油酸、亚麻酸、花生四烯酸、二十二碳六烯酸和二十碳五烯酸。The structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 20, wherein the unsaturated fatty acid comprises oleic acid, linoleic acid, linolenic acid, arachidonic acid, Docosahexaenoic acid and eicosapentaenoic acid.
  23. 制备权利要求20所述的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，包括：A method of preparing a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 20, comprising:
    (1)提供含有棕榈酸残基的甘油酯；(1) providing a glyceride containing a palmitic acid residue;
    (2)将含有棕榈酸残基的甘油酯与棕榈酸盐或棕榈酸非甘油酯混合进行酯交换，得到油脂A；(2) a glyceride containing a palmitic acid residue is mixed with palmitate or palmitic acid non-glyceride for transesterification to obtain a fat A;
    (3)将油脂A与不饱和脂肪酸进行Sn-1,3位酶促定向酯交换，得到混合油B； (3) The fat A and the unsaturated fatty acid are subjected to Sn-1, enzymatically transesterified transesterification to obtain a mixed oil B;
    (4)将混合油B精制，制得含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂。(4) The mixed oil B is purified to obtain a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
  24. 制备权利要求21所述的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，包括：A method of preparing a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 21, comprising:
    (1)提供未经过脱臭的含有棕榈酸残基的植物油毛油；(1) providing a vegetable oil containing a palmitic acid residue which has not been deodorized;
    (2)将含有棕榈酸残基的植物油毛油与不饱和脂肪酸或其非甘油酯进行Sn-1,3位酶促定向酯交换，得到混合油； (2) the vegetable oil oil containing the palmitic acid residue and the unsaturated fatty acid or its non-glyceride are subjected to the enzymatically transesterified transesterification of the Sn-1, 3 position to obtain a mixed oil;
    (3)将混合油精制，制得含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂。(3) The mixed oil is refined to obtain a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid.
  25. 根据权利要求24所述的制备含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，其特征在于：在步骤（1）和步骤（2）之间，增加对毛油进行随机酯交换的步骤。The method for preparing a structural fat or oil containing 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 24, wherein between step (1) and step (2), the addition of the oil is carried out. The step of random transesterification.
  26. 根据权利要求25所述的制备含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂的方法，其特征在于：在毛油进行随机酯交换的过程中，添加棕榈酸盐，且棕榈酸盐的添加量不超过植物油毛油重量的4倍。The method for producing a structural fat or oil containing a 1,3-diunsaturated fatty acid-2-palmitic acid according to claim 25, wherein palmitate is added during the random transesterification of the hair oil, and the palm The amount of the acid salt added is not more than 4 times the weight of the vegetable oil.
  27. 特殊膳食，其特征在于：该特殊膳食包含权利要求20至22任一项所述的含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂。A special diet comprising the 1,3-diunsaturated fatty acid-2-palmitic acid-containing structural fat or oil according to any one of claims 20 to 22.
  28. 根据权利要求27所述的特殊膳食，其特征在于：所述特殊膳食包括婴儿配方奶粉、婴幼儿配方米粉、儿童牛奶、儿童酸奶及消化功能异常病人的营养膳食。The special diet according to claim 27, wherein the special diet comprises an infant formula, an infant formula rice flour, a child milk, a child yogurt, and a nutritional meal of a patient with abnormal digestive function.
PCT/CN2015/082488 2014-07-07 2015-06-26 Composition comprising 2-palmitic acid glyceride and preparation method thereof, structural fat comprising 1, 3-diunsaturated fatty acid-2-palmitic acid and preparation method, and special food WO2016004825A1 (en)

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CN201410319597.6A CN104087626A (en) 2014-07-07 2014-07-07 Method for preparing composition containing 2-palmitin
CN201410319597.6 2014-07-07
CN201510220956.7A CN104830545B (en) 2015-05-05 2015-05-05 The Structure grease and preparation method of the bis- unrighted acid -2- palmitic acids containing 1,3-
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101198261A (en) * 2005-04-27 2008-06-11 恩兹默泰克有限公司 Human milk fat substitutes
CN101679909A (en) * 2007-02-28 2010-03-24 荷兰洛德斯克罗科兰有限公司 Process for producing a glyceride composition
CN104087626A (en) * 2014-07-07 2014-10-08 嘉必优生物工程（武汉）有限公司 Method for preparing composition containing 2-palmitin

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101198261A (en) * 2005-04-27 2008-06-11 恩兹默泰克有限公司 Human milk fat substitutes
CN101679909A (en) * 2007-02-28 2010-03-24 荷兰洛德斯克罗科兰有限公司 Process for producing a glyceride composition
CN104087626A (en) * 2014-07-07 2014-10-08 嘉必优生物工程（武汉）有限公司 Method for preparing composition containing 2-palmitin

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