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Method utilizing microwave assisted lipase catalysis to synthesize esterification modified EGCG

An esterification modification and microwave-assisted technology, which is applied in the field of biosynthesis of organic compounds, can solve the problems of introducing too many solvents, many reaction steps, and long time consumption, so as to speed up the reaction speed, increase the reaction yield, and shorten the reaction time. Effect

Active Publication Date: 2012-11-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many disadvantages in the acylation of EGCG by chemical method: poor regioselectivity, easy to produce a large amount of by-products, and low product yield; adopting measures such as group protection, many reaction steps, long time-consuming, and many solvents introduced, difficult to separate and purify; Alkaline catalyst, producing a large amount of alkali-containing waste liquid, etc.
At present, there is no report on the synthesis of modified EGCG by the combined action of microwave radiation and lipase catalysis

Method used

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  • Method utilizing microwave assisted lipase catalysis to synthesize esterification modified EGCG

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 50 mg of EGCG and 9.5 mL of vinyl acetate into a 50 mL round-bottomed flask with a stopper (the molar ratio of EGCG and vinyl acetate is 1:1), then add 20 mL of isopropanol, place the reactor in a microwave reaction device, and add 80U / g EGCG lipase LIPOZYME TL IM was reacted at 40°C and 40W for 30min. After the reaction was stopped, the reaction solution was filtered, rotary evaporated, and vacuum dried to obtain 35.8mg of EGCG esterification product with a recovery rate of 71.6%. The conversion rate of EGCG was analyzed by high performance liquid chromatography to be 65.4%.

[0016] Mass spectrometry analysis of EGCG acetylation products such as figure 1 shown.

[0017] A: The liquid chromatogram of the product after the acetylation reaction at 280nm; B: The mass spectrum selected ion map of the acetylated product (Mw=585) with 3 hydroxyl groups in the EGCG molecule; C: The acetylated 2 hydroxyl groups in the EGCG molecule MS-selected ion map of product (Mw=543)...

Embodiment 2

[0021] Add 50mg of EGCG and 16.1mL of vinyl butyrate into a 50mL round bottom flask with a stopper (the molar ratio of EGCG and vinyl butyrate is 1:1), then add 20mL of isopropanol, and place the reactor in a microwave reaction device , add 100U / g EGCG lipase Lipase AYS "Amano", react at 60°C and 50W for 40min, after stopping the reaction, the reaction solution is filtered, rotary evaporated, and vacuum dried to obtain 30.8 mg of EGCG esterification product, the recovery rate is 61.6 %. The conversion rate of EGCG was analyzed by high performance liquid chromatography to be 73.4%.

Embodiment 3

[0025] Add 150 mg of EGCG and 15.6 mL of vinyl hexanoate into a 100 mL round bottom flask with a stopper (the molar ratio of EGCG and vinyl hexanoate is 1.5:1), then add 40 mL of isopropanol, and place the reactor in a microwave reaction device. Add 100U / g EGCG lipase Lipase AYS "Amano" and react at 50°C and 60W for 50min. After the reaction is stopped, the reaction solution is filtered, rotary evaporated, and vacuum dried to obtain 81.5mg of EGCG esterification product, with a recovery rate of 81.5% . The conversion rate of EGCG was analyzed by high performance liquid chromatography to be 76.3%.

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Abstract

The invention relates to a method utilizing microwave assisted lipase catalysis to synthesize esterification modified EGCG (Epigallocatechin Gallate), and belongs to the biosynthesis filed of organic compounds. The method is characterized in that EGCG and fatty acid vinyl ester are taken as raw materials to synthesize the esterification modified EGCG through the co-action of microwave radiation and lipase catalysis in an organic solvent system, so that the product can be obtained. The method provided by the invention comprehensively utilizes the advantages of both the microwave radiation and the lipase catalysis, so as to achieve the effect which is not achieved by the lipase catalysis under a conventional heating condition. With the action of the microwave radiation, the reaction system can be uniformly affected by a microwave field, the heating rate of the system is high, the temperature is kept stable, the reaction is obviously accelerated, the reaction rate is improved, and the reaction time is greatly shortened. Therefore, the synthesis method provided by the invention is efficient and fast, and is consistent with the requirements of green chemistry.

Description

technical field [0001] The invention relates to a method for synthesizing esterification-modified EGCG with microwave-assisted lipase catalysis. Specifically, EGCG and fatty acid vinyl ester are used as raw materials to synthesize and modify EGCG through microwave radiation and lipase catalysis in an organic solvent system. EGCG belongs to the field of biosynthesis of organic compounds. Background technique [0002] Catechin is the most important physiologically active substance in tea, accounting for about 60%-80% of the total amount of tea polyphenols, and is the main material component of tea's health care function. Among the catechins, epigallocatechin gallate (EGCG) has the highest content, accounting for about 50% of the total catechins. Due to EGCG's excellent physiological activities such as anti-oxidation, anti-mutation, radiation protection, anti-tumor, immune regulation and anti-aging, recent researches on EGCG have attracted attention, but in terms of its applic...

Claims

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Application Information

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IPC IPC(8): C12P7/62
Inventor 王洪新朱松李哲马朝阳
Owner JIANGNAN UNIV
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