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Preparation method for catalytic synthesis of caffeic acid phenethyl ester by using lipase in ionic liquid

A technology of phenethyl caffeate and ionic liquids, applied in biochemical equipment and methods, methods based on microorganisms, microorganisms, etc., can solve the problems of high product yields, achieve high product yields, strengthen synthesis efficiency, and improve reaction conditions mild effect

Inactive Publication Date: 2012-01-18
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method is easy to operate, mild in reaction conditions, high in product yield, and environmentally friendly, thereby overcoming the shortcomings of traditional lipase catalyzed synthesis with low efficiency and low substrate solubility, and is easy to prepare high-purity phenethyl caffeate in large quantities. It is of great significance to promote its wide application in the pharmaceutical industry

Method used

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  • Preparation method for catalytic synthesis of caffeic acid phenethyl ester by using lipase in ionic liquid
  • Preparation method for catalytic synthesis of caffeic acid phenethyl ester by using lipase in ionic liquid
  • Preparation method for catalytic synthesis of caffeic acid phenethyl ester by using lipase in ionic liquid

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Experimental program
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Effect test

Embodiment 1

[0026] According to caffeic acid: phenylethyl alcohol=1: 1 (molar ratio) ratio prepares reaction system, according to caffeic acid: the ratio (mass ratio) of lipase=1: 1 adds catalyzer porcine pancreatic lipase, according to phenylethyl alcohol: ionic liquid= Add ionic liquid [Bmim][BF at a ratio of 1:1 (volume ratio) 4 ], the esterification reaction was carried out for 10 h at a reaction temperature of 10° C. and a shaking speed of 30 rpm. After the reaction, the conversion rate of the product of enzymatic synthesis of caffeic acid phenethyl ester detected by HPLC was 0.8%.

Embodiment 2

[0028] Prepare reaction system according to the ratio of caffeic acid: phenylethyl alcohol=1: 50 (molar ratio), add the free lipase of catalyzer Bacillus subtilis according to the ratio (mass ratio) of caffeic acid: lipase=1: 200, according to phenylethyl alcohol: ion The ratio (volume ratio) of liquid=1:200 is added into ionic liquid [TOMA][Tf 2 N], the esterification reaction was carried out for 150 h at a reaction temperature of 100° C. and a shaking speed of 250 rpm. After the reaction, the conversion rate of the product of enzymatic synthesis of caffeic acid phenethyl ester detected by HPLC was 8.8%.

Embodiment 3

[0030] Prepare the reaction system according to the ratio of caffeic acid: phenylethyl alcohol = 1: 10 (molar ratio), add the immobilized enzyme Novozym 435 of the catalyst Candida antarctica according to the ratio (mass ratio) of caffeic acid: lipase = 1: 5, according to the ratio of phenylethyl alcohol : ionic liquid = 1:30 ratio (volume ratio) to add ionic liquid [Bmim] [PF 6], the esterification reaction was carried out for 120 h at a reaction temperature of 80° C. and a shaking speed of 120 rpm. After the reaction, the product conversion rate of the enzymatic synthesis of caffeic acid phenethyl ester detected by HPLC was 44.5%.

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Abstract

The invention discloses a preparation method for catalytic synthesis of caffeic acid phenethyl ester by using lipase in an ionic liquid. The caffeic acid phenethyl ester is enzymatically synthesized in the ionic liquid which is selected as a reaction medium, the solubility of a substrate in the reaction medium is improved, and the thermal stability of the lipase and the stereoselectivity of the lipase to the substrate are improved. The method is easy to operate, is environment-friendly, and contributes to the large-scale preparation of the caffeic acid phenethyl ester, reaction conditions are mild, the yield of products is greatly improved, and the disadvantages that the efficiency of catalytic synthesis of the lipase by a conventional method is low and the solubility of the substrate is low are overcome.

Description

technical field [0001] The invention relates to the field of biochemical pharmacy, in particular to a preparation method for synthesizing caffeic acid phenethyl ester catalyzed by lipase in ionic liquid. Background technique [0002] Caffeic acid phenethyl ester, English name: Caffeic acid phenethyl ester (CAPE), chemical name: 2-phenylethyl-3-(3,4-dihydroxyphenyl)-2-acrylate, molecular formula: C 17 h 16 o 4 , molecular weight: 284.31. Caffeic acid phenethyl ester is the main functional ingredient in natural products such as propolis and rhodiola rosea. It has been proved by pharmacological experiments that it can block the production of active oxidative substances in neutrophils, block the xanthine oxidase system, and inhibit the The increase of NO can also inhibit the proliferation of tumor cells (Biol.Pharm.Bull, 2003, 26(4):487-491), and it is an auxiliary drug or active ingredient of drugs that major international pharmaceutical companies are competing to develop. ...

Claims

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Application Information

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IPC IPC(8): C12P7/62C12R1/72C12R1/66C12R1/80C12R1/645C12R1/785C12R1/07C12R1/38C12R1/01
Inventor 王俊吴福安李晶张磊霞顾双双郭锡杰
Owner JIANGSU UNIV OF SCI & TECH
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