WO2016004825A1 - Composition comprenant un glycéride d'acide 2-palmitique et son procédé de préparation, une graisse structurale comprenant l'acide 2-palmitique acide gras 1,3-bi-insaturé et procédé de préparation, et aliments spéciaux - Google Patents

Composition comprenant un glycéride d'acide 2-palmitique et son procédé de préparation, une graisse structurale comprenant l'acide 2-palmitique acide gras 1,3-bi-insaturé et procédé de préparation, et aliments spéciaux 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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Prior art keywords
palmitic acid
glyceride
acid
oil
composition containing
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PCT/CN2015/082488
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English (en)
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/zh
Priority claimed from CN201510220956.7A external-priority patent/CN104830545B/zh
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/fr

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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

L'invention concerne une composition comprenant un glycéride d'acide 2-palmitique et un procédé de préparation de celui-ci, et, prévoit en outre, une graisse structurale contenant de l'acide 2-palmitique acide gras 1,3-bi-insaturé et un procédé de préparation. Le procédé de préparation de la composition comprend : (1) la fourniture d'un glycéride comprenant un résidu d'acide palmitique; (2) le mélange du glycéride comprenant le résidu d'acide palmitique avec de l'acide palmitique, un sel de celui-ci ou un non-glycéride d'acide palmitique pour conduire un échange d'ester de manière à obtenir une huile A; (3) la conduite d'une interestérification dirigée enzymatique au site Sn-1,3 sur l'huile A et l'acide gras insaturé ou son non-glycéride afin d'obtenir une huile mixte B; et (4) le raffinage de l'huile mixte B pour obtenir la composition comprenant le glycéride d'acide 2-palmitique.
PCT/CN2015/082488 2014-07-07 2015-06-26 Composition comprenant un glycéride d'acide 2-palmitique et son procédé de préparation, une graisse structurale comprenant l'acide 2-palmitique acide gras 1,3-bi-insaturé et procédé de préparation, et aliments spéciaux WO2016004825A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201410319597.6 2014-07-07
CN201410319597.6A CN104087626A (zh) 2014-07-07 2014-07-07 含有2-棕榈酸甘油酯的组合物的制备方法
CN201510220956.7 2015-05-05
CN201510220956.7A CN104830545B (zh) 2015-05-05 2015-05-05 含1,3-二不饱和脂肪酸-2-棕榈酸的结构油脂及制备方法

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101198261A (zh) * 2005-04-27 2008-06-11 恩兹默泰克有限公司 人乳脂替代品
CN101679909A (zh) * 2007-02-28 2010-03-24 荷兰洛德斯克罗科兰有限公司 甘油酯组合物的制备方法
CN104087626A (zh) * 2014-07-07 2014-10-08 嘉必优生物工程（武汉）有限公司 含有2-棕榈酸甘油酯的组合物的制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101198261A (zh) * 2005-04-27 2008-06-11 恩兹默泰克有限公司 人乳脂替代品
CN101679909A (zh) * 2007-02-28 2010-03-24 荷兰洛德斯克罗科兰有限公司 甘油酯组合物的制备方法
CN104087626A (zh) * 2014-07-07 2014-10-08 嘉必优生物工程（武汉）有限公司 含有2-棕榈酸甘油酯的组合物的制备方法

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