Selective preparation method for 5-site and 7-site ester catechin molecules

A technology of molecular selectivity and ester-based catechin, applied in organic chemistry and other fields, can solve the problem of no esterification, etc., and achieve good selectivity, simple operation, and good application prospects

Active Publication Date: 2015-02-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are methods for the preparation of mixed ester-based catechins, there is no effective method for esterification at a specific position

Method used

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  • Selective preparation method for 5-site and 7-site ester catechin molecules
  • Selective preparation method for 5-site and 7-site ester catechin molecules
  • Selective preparation method for 5-site and 7-site ester catechin molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Catechin (29 mg), benzyl chloroformate (40 mg) and triethylamine (30 mg) were stirred and reacted at room temperature for 2 hours, extracted with ethyl acetate after the reaction, and purified by column chromatography to obtain 3',4 '-Dibenzyloxycarbonyl ester catechin, 3',4'-dibenzyloxy carbonyl ester catechin was dissolved in an organic solvent, added lauryl chloride (22mg) and triethylamine (15mg) at room temperature The reaction was stirred for 2 hours. After the reaction was completed, it was extracted with ethyl acetate and purified by column chromatography to obtain 3',4'-dibenzyloxycarbonyl-5-dodecanoyl catechin and 3' ',4'-dibenzyloxycarbocarboxy-7-dodecanoyl catechin catechin mixture. Then dissolve in methanol, add 5% palladium carbon (11 mg) and triethylsilane (120 mg), stir and react at room temperature for 12 hours, extract with ethyl acetate after the reaction is completed, and obtain 5- Lauryl catechin (yield: 15%, eluent is chloroform methanol mixed sol...

Embodiment 2

[0043] Catechin (29 mg), benzyl chloroformate (34 mg) and tripropylamine (36 mg) were stirred at room temperature for 2 hours, extracted with ethyl acetate after the reaction, and purified by chromatography to obtain 3',4'-di Benzyloxycarbonyl ester catechins. Dissolve 3',4'-dibenzyloxycarbonyl ester catechin in an organic solvent, add acetic anhydride (11mg) and N,N-diisopropylethylamine (15mg) and stir at room temperature for 2 hours. After extraction with ethyl acetate, after purification by column chromatography, 3',4'-dibenzyloxycarbonyl-5-acetyl catechin and 3',4'-dibenzyloxycarbonyl- 7-Acetoxylate catechin mixture. Then it was dissolved in methanol, 5% palladium carbon (1.4 mg) and triethylsilane (120 mg) were added, and the reaction was stirred at room temperature for 12 hours. After the reaction was completed, it was extracted with ethyl acetate, and purified by column chromatography to obtain 5 - Acetyl ester catechin (yield: 11%, the eluent is a mixed solvent of c...

Embodiment 3

[0045] Catechin (29mg), benzyl chloroformate (40mg) and N,N-diisopropylethylamine (33mg) were stirred and reacted at room temperature for 2 hours, extracted with ethyl acetate after the reaction was completed, and purified by chromatography The 3',4'-dibenzyloxycarbonyl ester catechin was obtained. Dissolve 3',4'-dibenzyloxycarbonyl ester catechin in an organic solvent, add acetic anhydride (11 mg) and tripropylamine (17 mg) and stir at room temperature for 2 hours, and extract with ethyl acetate after the reaction is complete. After purification by column chromatography, 3',4'-dibenzyloxycarbonyl-5-acetoyl catechin and 3',4'-dibenzyloxycarbonyl-7-acetyl catechin were obtained mixture. Then it was dissolved in methanol, 5% palladium carbon (1.4 mg) and triethylsilane (120 mg) were added, and the reaction was stirred at room temperature for 12 hours. After the reaction was completed, it was extracted with ethyl acetate, and purified by column chromatography to obtain 5 - Acet...

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Abstract

The present invention discloses a selective preparation method for 5-site and 7-site ester catechin molecules. The selective preparation method comprises: dissolving catechin in acetonitrile, adding benzyl chloroformate and tertiary amine, reacting to obtain 3',4'-dibenzyloxycarbonyl ester catechin, carrying out an acylation reaction of the 3',4'-dibenzyloxycarbonyl ester catechin in the presence of an acylation agent and the tertiary amine to obtain a mixture of 3',4'-dibenzyloxycarbonyl ester-5-ester catechin and 3',4'-dibenzyloxycarbonyl ester-7-ester catechin, and removing the benzyloxycarbonyl from the 3',4'-dibenzyloxycarbonyl ester-5-ester catechin and the 3',4'-dibenzyloxycarbonyl ester-7-ester catechin to obtain the 5-ester catechin and the 7-ester catechin. According to the present invention, the product obtained by adopting the preparation method has characteristics of high purity, good selectivity and good application prospect; and the preparation method has the simple operation, and is suitable for industrial production application.

Description

technical field [0001] The invention belongs to the technical field of research and development of functional foods and medicines, and in particular relates to a method for selectively preparing 5- and 7-ester catechin molecules. Background technique [0002] Polyphenols are a class of polyhydric phenolic substances widely present in plants. They are contained in the leaves, wood, skin, shell and pulp of plants, and the skins of fruits and grains contain high levels of plant polyphenols. Polyphenols have an excellent antioxidant effect, which is the basis of all their physiological activities. A large number of in vivo and in vitro experiments and epidemiological data show that eating a certain amount of plant polyphenols can prevent and inhibit diseases. Polyphenols have anti-arteriosclerosis, prevention and treatment of cardiovascular diseases such as coronary heart disease and stroke, as well as anti-inflammatory, anti-allergic and anti-viral effects. With the developm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/62
CPCC07D311/62
Inventor 刘松柏洪姗
Owner ZHEJIANG UNIV
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