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Method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol

A technology of palmitoylglycerol and acetylglycerol, which is applied in the preparation of carboxylic acid esters, asymmetric anhydrides, and carboxylic acid halides, etc., can solve the problems of reduced stability, reduced reaction yield, and decomposition of reaction products, and achieves inhibition Formation of impurities or degradation products, effect of high yield

Pending Publication Date: 2021-04-16
ENZYCHEM LIFESCI CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when acetyl chloride or acetyl bromide is used as an acetylating agent, a strong acid such as hydrochloric acid or bromic acid is produced as a reaction by-product, its stability decreases as the reaction time increases, and the reaction product may decompose
In this case, the reaction yield may be reduced and additional purification steps may be required to increase the purity of the product

Method used

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  • Method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol
  • Method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol
  • Method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol

Examples

Experimental program
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Effect test

Embodiment 1

[0034] [Example 1] Preparation of 1-palmitoyl-3-acetylglycerol intermediate

[0035] Into a 250 mL three-neck round bottom flask were added 20 g of 1-palmitoylglycerol, 140 mL of dichloromethane, 33.5 g of pyridine, and 0.15 g of dimethylaminopyridine, and the mixture was heated to 30° C. to dissolve 1-palmitoyl glycerin. 3.1 g of acetic anhydride was added dropwise while maintaining the temperature of the reactant at 18°C, 5.7 g of acetyl chloride and 11 mL of dichloromethane were added dropwise while maintaining the temperature at 5°C, and the reaction was allowed to proceed for 18 hours. After the reaction was completed, 90 mL of purified water and 40 g of concentrated hydrochloric acid were added, the temperature was raised to 25° C., and the aqueous layer was separated to obtain an organic layer. The obtained organic layer was further subjected to a layer separation process using purified water again. Magnesium sulfate and potassium carbonate were added to the separate...

Embodiment 2

[0036] [Example 2] Preparation of 1-palmitoyl-3-acetylglycerol intermediate

[0037] 30 g of 1-palmitoylglycerol, 180 mL of dichloromethane, 50.3 g of pyridine, and 0.22 g of dimethylaminopyridine were added to a 250 mL three-neck round bottom flask, and the mixture was heated to 25-30° C. to dissolve 1- Palmitoyl Glycerin. While maintaining the temperature of the reactant at 18°C, 9.2 g of acetic anhydride was added dropwise. After the dropwise addition, the temperature was maintained at 5°C, and the reaction was performed for 22 hours.

[0038] After the reaction was completed, 90 mL of purified water and 40 g of concentrated hydrochloric acid were added, the temperature was raised to 25° C., and the aqueous layer was separated to obtain an organic layer. The obtained organic layer was further subjected to a layer separation process using purified water again. Magnesium sulfate and potassium carbonate were added to the separated organic layer, stirred for 1 hour, then ma...

Embodiment 3

[0039] [Example 3] Preparation of 1-palmitoyl-2-linoleoyl-3-acetylglycerol

[0040] Add 7.67g of linoleic acid, 80mL of n-hexane and 3.31g of pivaloyl chloride to a 250mL three-neck round bottom flask, and cool the reactant to -5~10°C, and dropwise add 5.97g of triethylamine . After adding 10 g of 1-palmitoyl-3-acetylglycerol and 0.328 g of 4-dimethylaminopyridine to the reactant, the reactant was reacted for 12 hours while stirring under nitrogen.

[0041] After the reaction was completed, 40 mL of purified water was added to the reactant, and the aqueous layer was subjected to layer separation to obtain a washed organic layer. Add 27 mL of methanol and 13.5 mL of a mixed solution of 0.1 N KOH to the separated organic layer, wash twice, then wash with 40 mL of a mixed solution of 95 volume % methanol and pure water, and wash with 10 mL of 0.1 volume % hydrochloric acid, It was then washed with 40 mL of 0.05% by weight aqueous sodium bicarbonate. To the washed organic lay...

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Abstract

Disclosed is a method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol of high purity with high yield by carrying out acetylation of 1-palmitoyl glycerol with acetic anhydride or a mixture of acetic anhydride and acetyl chloride. The method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol comprises the steps of: preparing 1-palmitoyl-3-acetyl glycerol intermediate of Chemical formula 2 in the specification by reacting 1-palm itoyl glycerol of Chemical formula 1 in the specification and an acetylating agent selected from the group consisting of (i) acetic anhydride and (ii) a mixture of acetic anhydride and acetyl chloride; and reacting the 1-palmitoyl-3-acetyl glycerol intermediate and linoleic acid. The method suppresses the formation of impurities or degradation products and does not need an additional purification step.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of Korean Patent Application No. 10-2019-0128021 filed on October 15, 2019, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present invention relates to a method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol, more particularly to a method by making 1-palmitoylglycerol and acetic anhydride or acetic anhydride and acetyl chloride A method for producing high-purity 1-palmitoyl-2-linoleoyl-3-acetylglycerol in high yield by performing acetylation. Background technique [0004] rac-1-palmitoyl-2-linoleoyl-3-acetylglycerol, one of the components of velvet antler, is isolated from the chloroform extract of velvet antler, and has a growth-stimulating effect on hematopoietic stem cells and megakaryocytes ( Korean Patent No. 10-0283010). Korean Patent Nos. 10-0291743, 10-1278874 and the like disclose chemical synthesis methods...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/587C07C67/29C07C69/30
CPCC07C67/08C07C67/14C07C69/30C07C69/587C07C69/604C07C69/003B01J31/0244C07C67/12
Inventor 孙起荣姜炳圭
Owner ENZYCHEM LIFESCI CORP
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