Biosynthesis method of caffeic acid phenethylester by means of transesterification

Abstract

The invention discloses a biosynthesis method of caffeic acid phenethylester by means of transesterification. The caffeic acid phenethylester is prepared by reacting caffeic acid alkyl ester with phenylethyl alcohol in an ionic liquid by taking the ionic liquid as a reaction medium and lipase as a catalyst, the caffeic acid alkyl ester and the phenylethyl alcohol are added at a molar ratio of 1:(1-40), the lipase is added according to the molar ratio of the caffeic acid alkyl ester to the lipase of 1:(1-40), the ionic liquid is added according to the volume ratio of the phenylethyl alcohol to the ionic liquid of 1:(5-50), reaction temperature is 40-90 DEG C, oscillation rotation speed is 120-300 rpm (revolutions per minute), and reaction time is 10-72 hours. The transesterification method provided by the invention takes the ionic liquid as the reaction medium, is capable of increasing the solubility of a substrate with a product, improving the catalytic activity and reaction efficiency of an enzyme and shortening the reaction time, is simple in operation, mild in conditions, high in product yield, and environmentally-friendly, and has good application prospect.

Description

Technical field

[0001] The invention belongs to the technical field of pharmacy, and relates to a drug synthesis process, in particular to a method for transesterification and biosynthesis of caffeic acid phenethyl ester. Background technique

[0002] Caffeic acid phenethyl ester, the English name is Caffeic acid phenethyl ester (CAPE), and the chemical name is 3-(3′,4′-dihydroxyphenyl)-2-acrylic acid phenethyl ester. It is the most important active ingredient in propolis one. Studies have shown that caffeic acid phenethyl ester has a variety of biological activities such as antioxidant, anti-inflammatory, anti-tumor, immune regulation, and treatment of diabetes (Pharmacological Research, 2009, 60:270-276). It is used in the fields of medicine, food and health products. The broad application prospects of, arouse more and more attention.

[0003] To separate and extract caffeic acid phenethyl ester from natural plants, such methods usually require the use of a large amount of orga...

Examples

Embodiment 1

[0021] With caffeic acid heptyl ester as the reaction substrate, the molar ratio of caffeic acid heptyl ester: phenyl alcohol is 1:1, the mass ratio of caffeic acid heptyl ester: lipase Lipozyme TLIM is 1: 1, phenyl alcohol: ionic liquid [TOMA ][HSO 4 ] The volume ratio is 1:5 to prepare a reaction system, and react for 10 hours at 40°C and at a rotating speed of 120 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 42.7%.

Embodiment 2

[0023] Using caffeic acid butyl ester as the reaction substrate, according to the molar ratio of caffeic acid butyl ester: phenethyl alcohol is 1:40, the mass ratio of caffeic acid butyl ester: lipase Novozym435 is 1:40, and phenyl alcohol: ionic liquid [Omim] [BF 4 ] The volume ratio is 1:50 to form a reaction system, and react for 48 hours at 90°C and 300 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 71.7%.

Embodiment 3

[0025] Ethyl caffeate is used as the reaction substrate, and the molar ratio of ethyl caffeate: phenethyl alcohol is 1:14, the mass ratio of ethyl caffeate: industrial lipase is 1:30, and the mass ratio of phenethyl alcohol: ionic liquid [Bmim ][Tf 2 The volume ratio of N] is 1:20 to form a reaction system, and the reaction system is reacted for 40 hours at 70°C and at a rotation speed of 180 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 63.2%.

Technical field

[0001] The invention belongs to the technical field of pharmacy, and relates to a drug synthesis process, in particular to a method for transesterification and biosynthesis of caffeic acid phenethyl ester. Background technique

[0002] Caffeic acid phenethyl ester, the English name is Caffeic acid phenethyl ester (CAPE), and the chemical name is 3-(3′,4′-dihydroxyphenyl)-2-acrylic acid phenethyl ester. It is the most important active ingredient in propolis one. Studies have shown that caffeic acid phenethyl ester has a variety of biological activities such as antioxidant, anti-inflammatory, anti-tumor, immune regulation, and treatment of diabetes (Pharmacological Research, 2009, 60:270-276). It is used in the fields of medicine, food and health products. The broad application prospects of, arouse more and more attention.

[0003] To separate and extract caffeic acid phenethyl ester from natural plants, such methods usually require the use of a large amount of orga...

Examples

Embodiment 1

[0021] With caffeic acid heptyl ester as the reaction substrate, the molar ratio of caffeic acid heptyl ester: phenyl alcohol is 1:1, the mass ratio of caffeic acid heptyl ester: lipase Lipozyme TLIM is 1: 1, phenyl alcohol: ionic liquid [TOMA ][HSO 4 ] The volume ratio is 1:5 to prepare a reaction system, and react for 10 hours at 40°C and at a rotating speed of 120 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 42.7%.

Embodiment 2

[0023] Using caffeic acid butyl ester as the reaction substrate, according to the molar ratio of caffeic acid butyl ester: phenethyl alcohol is 1:40, the mass ratio of caffeic acid butyl ester: lipase Novozym435 is 1:40, and phenyl alcohol: ionic liquid [Omim] [BF 4 ] The volume ratio is 1:50 to form a reaction system, and react for 48 hours at 90°C and 300 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 71.7%.

Embodiment 3

[0025] Ethyl caffeate is used as the reaction substrate, and the molar ratio of ethyl caffeate: phenethyl alcohol is 1:14, the mass ratio of ethyl caffeate: industrial lipase is 1:30, and the mass ratio of phenethyl alcohol: ionic liquid [Bmim ][Tf 2 The volume ratio of N] is 1:20 to form a reaction system, and the reaction system is reacted for 40 hours at 70°C and at a rotation speed of 180 rpm. After the reaction, the sample was tested by HPLC, and the yield of caffeic acid phenethyl ester was calculated to be 63.2%.

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