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Preparation method of fully substituted acetylate of epigallocatechin-gallate (EGCG)

A technology of epigallocatechin and gallocatechin, which is applied in the field of preparation of its fully substituted acetylated compounds, can solve problems such as synthesis or preparation of unseen systems, difficulty in achieving targeting, retention of acetylated compounds, etc., and achieve high stability and bioavailability, convenient research and application, mild reaction conditions

Inactive Publication Date: 2009-09-02
TEA RES INST CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The unique and extensive physiological activity of EGCG is the basis of its application, but there are still the following problems in terms of its application: 1. The water solubility of EGCG limits its application in lipid products, especially as an antioxidant of oils; Due to the poor fat solubility in the body, it is difficult to penetrate the double lipid layer cell membrane, and it is difficult to reach the target point of action, which greatly reduces its due activity
2. EGCG is prone to various metabolic reactions in the living body, and its poor stability in the physiological environment in the body leads to its low bioavailability
However, the acetylated compound involved is still in the experimental stage and lacks research on other physiological activities, and there is no systematic research and report on its synthesis or preparation.

Method used

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  • Preparation method of fully substituted acetylate of epigallocatechin-gallate (EGCG)
  • Preparation method of fully substituted acetylate of epigallocatechin-gallate (EGCG)
  • Preparation method of fully substituted acetylate of epigallocatechin-gallate (EGCG)

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Experimental program
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Effect test

Embodiment 1

[0024] Weigh 0.46g of the EGCG sample in 100ml of chloroform solution, add 8ml of acetic anhydride and 1ml of pyridine (the ratio of substrate EGCG to acetic anhydride is more than 1:80), stir and react on a magnetic stirrer at room temperature for 5h, and the rotating speed is 300rpm, At the end of the reaction, 10 mL of distilled water was added to terminate the reaction system, and the EGCG fully substituted acetylated product was obtained, the content of which was more than 95.60%.

Embodiment 2

[0026] Weigh 0.46g of the EGCG sample in 100ml of chloroform solution, add 15ml of acetic anhydride and 1ml of pyridine (the ratio of substrate EGCG to acetic anhydride is 1:159.0), stir and react on a magnetic stirrer at room temperature for 5h, the rotating speed is 400rpm, and the reaction At the end, 10 mL of distilled water was added to terminate the reaction system to obtain the fully substituted acetylated product of EGCG, wherein the conversion rate of EGCG reached 98.20%.

Embodiment 3

[0028] Weigh 0.46g of the EGCG sample in 100ml of chloroform solution, add 20ml of acetic anhydride and 1ml of pyridine (the ratio of substrate EGCG to acetic anhydride is more than 1:200), stir and react on a magnetic stirrer at room temperature for 5h, the rotating speed is 300rpm, At the end of the reaction, 10 mL of distilled water was added to terminate the reaction system, and the EGCG fully substituted acetylated product was prepared, and its content reached more than 98.50%.

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Abstract

The invention discloses a preparation method of fully substituted acetylate of epigallocatechin-gallate (EGCG) by taking EGCG as materials. The acetylate of EGCG obtained by the existing method has different substituting degree until full substituted substance and the fully substituted acetylate has low purity, which is adverse for further research and application. The invention takes EGCG and acetylation reagent as substrates, an acetylate reaction happens in the presence of an organic solvent and a pyridine catalyst, the mole ratio between EGCG and the acetylate reagent is controlled within the range of 1:80-200, and the fully substituted acetylate of EGCG is generated by the reaction and the products are purified then. The invention can obtain fully substituted acetylate with high purity, which is convenient for further research and application.

Description

technical field [0001] The invention relates to a method for preparing the fully substituted acetylate of epigallocatechin gallate as a raw material. Background technique [0002] Natural catechins are the most important physiologically active substances in tea, mainly including epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECG) and epigallocatechin gallate There are 4 kinds of acid esters (EGCG), which account for about 60%-80% of the total amount of tea polyphenols. Among them, EGCG has the highest content and the strongest activity, and its research has attracted the most attention in recent years. Modern scientific research shows that EGCG has significant anti-oxidation, anti-mutation, anti-radiation, antibacterial and disinfection effects, can enhance the function of the immune system, inhibit the growth of fat and cholesterol, inhibit the growth of tumors, and have preventive effects on cardiovascular diseases and AIDS. [0003] The unique and extens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/62
Inventor 江和源刘晓辉张建勇袁新跃
Owner TEA RES INST CHINESE ACAD OF AGRI SCI
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