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Method for preparing difatty acyl phosphatidylcholine by solid-phase reaction

A technology for fatty acyl phosphatidyl choline and glycerol phosphatidyl choline, which is applied in the field of preparation of pharmaceutical and chemical products, can solve the problems of high cost and unfavorable industrialization, and achieves the effects of low cost, realization of industrialized production and short production cycle.

Inactive Publication Date: 2019-12-13
NANJING WELL CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The technical problem to be solved in the present invention is that in the semi-synthetic method of di-fatty acyl phosphatidylcholine, when using diatomite dry method to load glycerol phosphatidylcholine, in order to avoid its sticking to the wall, it is necessary to use an expensive polytetrafluoroethylene container , high cost, not conducive to industrialization

Method used

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  • Method for preparing difatty acyl phosphatidylcholine by solid-phase reaction
  • Method for preparing difatty acyl phosphatidylcholine by solid-phase reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 10 g of glycerol phosphatidylcholine and 20 mL of methanol into a 250 mL three-necked flask, and dissolve under stirring at room temperature. Add 20 g of alumina, continue to stir for 1 h, and recover the methanol solvent by distillation under reduced pressure, and vacuum-dry the obtained solid-phase loading mixture for future use.

[0026] Add 160mL of dichloromethane and 55g of stearic acid into a 500mL three-neck flask, heat up to reflux with stirring until the stearic acid dissolves, slowly add 40g of N,N'-dicyclohexylcarbodiimide (DCC), and continue to reflux after the addition is complete 2h. 30 g of alumina-loaded glycerol phosphatidylcholine mixture was added to the above reaction solution, and TLC was followed until the end of the reaction. Alumina was recovered by filtration, dichloromethane was recovered by spin-drying, and the crude solid obtained was beaten with 200 mL of acetone at room temperature to remove impurities. After beating three times, 20....

Embodiment 2

[0028] Add 50 g of glycerol phosphatidylcholine and 100 mL of ethanol into a 500 mL three-necked flask, and dissolve under stirring at 50°C. 50 g of silica gel was added, stirring was continued for 1 h, the ethanol solvent was recovered by distillation under reduced pressure, and the obtained solid-phase loading mixture was vacuum-dried for future use.

[0029] Add 800mL of n-heptane and 275g of oleic acid into a 1000mL three-neck flask, heat up to reflux with stirring until the oleic acid dissolves, slowly add 155g of N,N'-carbonyldiimidazole (CDI), and continue to reflux for 2 hours after the addition is complete. Add 100 g of silica gel-loaded glycerol phosphatidylcholine mixture to the above reaction solution, and track it by TLC until the end of the reaction. Silica gel was recovered by filtration, n-heptane was recovered by spin-drying, and the crude solid obtained was beaten with 2000 mL of methyl tert-butyl ether at room temperature to remove impurities. After beating...

Embodiment 3

[0031] Add 10 g of glycerol phosphatidylcholine and 40 mL of isopropanol into a 250 mL three-necked flask, and dissolve under stirring at room temperature. Add 30 g of alumina, continue to stir for 1 h, and recover the isopropanol solvent by distillation under reduced pressure, and vacuum-dry the obtained solid-phase loaded mixture for future use.

[0032] Add 160mL of chloroform and 40g of stearic acid into a 500mL three-neck flask, heat up to reflux with stirring until the stearic acid dissolves, and slowly add 32g of N,N'-dicyclohexylcarbodiimide (DCC). Add 40 g of the alumina-supported glycerol phosphatidylcholine mixture into the above reaction solution, and track the reaction until the end of the reaction by TLC. Alumina was recovered by filtration, chloroform was recovered by spin-drying, and the crude solid obtained was beaten with 300 mL of methyl isobutyl ketone at room temperature to remove impurities. After beating three times, 20.4 g of high-purity distearoylphos...

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Abstract

The invention relates to a method for preparing difatty acyl phosphatidylcholine by a solid-phase reaction. Glycerol phosphatidylcholine is subjected to wet-process loading by using a high-activity solid adsorbent, and then a condensation reaction is carried out on the glycerol phosphatidylcholine with fatty acid to obtain the difatty acyl phosphatidylcholine. The method comprises the following steps: dissolving glyceryl phosphatidylcholine in an organic solvent, adding a high-activity solid adsorbent, carrying out adsorbing dispersion while stirring, removing the organic solvent by vacuum evaporation, and carrying out vacuum drying on the obtained solid-phase loaded mixed material; dissolving fatty acid in an organic solvent, adding a condensation coupling agent, carrying out heating reflux to prepare active ester of fatty acid, adding the solid-phase loaded glyceryl phosphatidylcholine, and continuing reflux to prepare a difatty acyl phosphatidylcholine crude product; and carrying out filtering to recover the high-activity solid adsorbent, desolventizing mother liquor, pulping a crude product by using an organic solvent, and carrying out recrystallizing to obtain the high-puritydifatty acyl phosphatidylcholine. According to the method, the reaction yield reaches 65% or above, the product purity reaches 99% or above, the process is simple, the production period is short, andindustrial production is easy to achieve.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical and chemical products, and in particular relates to a preparation method for difatty acylphosphatidylcholines to synthesize phospholipids. Background technique [0002] Phospholipids are an important part of biological membranes. Their amphiphilicity, which contains both hydrophilic groups and lipophilic groups, enables them to spontaneously form closed bilayers in aqueous media and become the framework of biological membranes. In addition to their usual biological functionality, phospholipids are used as emulsifiers in food, pharmaceuticals and cosmetics, and as liposomal packaging in pharmaceuticals. Although as early as 1971, the British Liman et al. used liposomes as drug carriers, but natural phospholipids have disadvantages such as easy oxidation and poor stability, thus limiting their application as liposome packaging materials in pharmaceuticals. [0003] Synthetic p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
CPCC07F9/091
Inventor 吴明朗靳垒
Owner NANJING WELL CHEM
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