Antioxidant EGCG aliphatic ester and prep. thereof

A technology of fatty acid esters and antioxidants, applied in chemical instruments and methods, compositions for inhibiting chemical changes, organic chemistry, etc., can solve problems such as incomplete determination of molecular structure, impact on product antioxidant effect, safety issues, etc. Achieve high stability, complete transformation and mild reaction

Inactive Publication Date: 2003-10-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patents CN1197786A and CN1263083A report the modification of water-soluble tea polyphenols into fat-soluble tea polyphenols, but due to the strong acidic environment in the reaction process, the formation of condensation products such as "red powder" cannot be controlled, thus affecting the antioxidant effect of the product
Although the patent CN1231277A has c

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Take 2.00g (4.36mmol) of EGCG monomer, dissolve it in 20mL of ethyl acetate, add 5g of potassium bicarbonate, heat to 40°C, add 1.20g (4.36mmol) of palmitoyl chloride dropwise within 30min, and continue to keep warm for 1.5h , the reaction solution should be a colorless and transparent liquid. Filter after stopping the reaction, wash the filtrate with water, concentrate under reduced pressure, recrystallize, and then dehydrate and dry to obtain white powder containing about 75 % (w / w) composition of EGCG fatty acid ester 3.0 g.

Embodiment 2

[0016] Take 2.00g (4.36mmol) of EGCG monomer, dissolve it in 20mL of diethoxymethane, add 5g of potassium bicarbonate, heat to 45°C, add 1.32g (4.36mmol) of stearyl chloride dropwise within 30min, and keep warm for reaction Filtrate after 2 hours, wash the filtrate with water, concentrate under reduced pressure, recrystallize, and then dehydrate and dry to obtain white powder containing about 80% of epigallocatechin-3-O-gallic acid-4'-O-fatty acid ester (w / w) composition of EGCG fatty acid ester 3.1 g.

Embodiment 3

[0018] Take 5.00g (10.91mmol) of EGCG monomer, dissolve it in 20mL of tetrahydrofuran, add 1g of zinc catalyst, heat to 40°C, add 2.38g (10.87mmol) of lauroyl chloride dropwise within 45min, keep warm for 1.5h and then filter, the filtrate Washed with water, concentrated under reduced pressure, recrystallized, and then dehydrated and dried to obtain white powder containing about 70% (w / w) of epigallocatechin-3-O-gallic acid-4'-O-fatty acid ester Composition of EGCG fatty acid ester 6.9g.

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PUM

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Abstract

The EGCG fatty ester is prepared with natural catechin EGCG monomer and C12-C22 fatty acyl chloride in the molar ratio of 1-2 as material. In the presence of alkali catalyst or metal catalyst and in25-65 deg.c, fatty acyl chloride is dropped slowly into inert organic solvent containing catechin EGCG monomer; and through filtering, water washing, decompression concentration, re-crystallization and dewatering to dry, white solid EGCG fatty ester is prepared. The liposoluble EGCG fatty ester thus prepared has determined components, high antioxidant factor content, molecular structure capable of maintaining the structure features of catechin and even higher stability. The present invention may be used in medicine, edible vegetable oil, fried food, cosmetics, feed and other fields needing antioxidant additive.

Description

technical field [0001] The invention relates to an antioxidant EGCG fatty acid ester and a preparation method thereof. Background technique [0002] Oxidation is one of the important factors leading to the deterioration of the quality of food and cosmetics. Adding antioxidants with high safety and good effect is one of the common methods to prevent oxidative deterioration. Due to the potential Toxicity limits their widespread use. In recent years, with people's increasing demand and trust in natural antioxidants, tea polyphenols in green tea have been widely used in food, cosmetics and other industries because of their strong free radical scavenging ability and antioxidant activity. A rare natural antioxidant. Most of the tea polyphenols are catechins, among which the content of epigallocatechin-3-O-gallate (EGCG) is the highest. Since tea polyphenols are easily soluble in water, which prevents them from being fully effective in fat-soluble syste...

Claims

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Application Information

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IPC IPC(8): C07D311/62C09K15/06
Inventor 陈平
Owner ZHEJIANG UNIV
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