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Preparation method for caffeic acid phenethyl ester

A technology of phenethyl caffeate and caffeic acid, which is applied in the field of preparation of phenethyl caffeate, can solve the problems of expensive materials, large environmental pollution, and many extraction steps, and achieve mild reaction conditions, small environmental pollution, and easy operation. simple effect

Inactive Publication Date: 2014-05-21
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are many methods for preparing phenethyl caffeate at home and abroad, but most of them have relatively large shortcomings, which still need to be solved.
Jin U et al. (Jin U, Chung T, Kang S, et al. Caffeic acid phenyl ester in propolis is inhibitor of matrix metalloproteinase-9 and invasion inhibitor: lso-and identifications J.Clin Chun Acxa, 2005, 362( 1 / 2) 57- 64) reported that methanol, ethanol and other solvents from natural plant propolis Extraction, but there are many extraction steps, long time and low efficiency, and the extraction of medicinal ingredients from natural plants also has the disadvantage of difficult separation and purification in the later stage
[0004] Liu Feng (Liu Feng. Preparation and biological activity of caffeic acid ester derivatives [D]. Hangzhou: Zhejiang University of Technology, 2006.) reported that using toluene as solvent, isopropylidene malonate and phenylethyl alcohol reacted first , after adding 3,4-dihydroxybenzaldehyde, pyridine and piperidine to prepare phenethyl caffeate, the method is expensive in materials, large in environmental pollution, cumbersome in post-treatment, and low in yield
[0005] Kishimoto N et al. (Kishimoto N, Kakino Y, Iwai K, et al. Enzymatic synthesis of caffeic acid esters from chlorogenic acid by transesterification and condensation reactions[J].Colloq Sci Int Café,2005,20:249-253) reported that chlorogenic acid hydrolase catalyzed chlorogenic acid and phenylethyl alcohol, β-phenyl bromide Ethane reacts to produce phenethyl caffeate. Although this biosynthesis method has a high conversion rate, it involves high costs in the field of enzyme engineering and is not suitable for general industrial production.

Method used

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  • Preparation method for caffeic acid phenethyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Take 10g of caffeic acid, stir and dissolve it in 100mL of DMF and pour it into a round-bottomed flask, then add 30g of potassium bicarbonate as a catalyst, then add 9mL of β-phenylbromoethane, heat and stir under reflux at 80°C for 5 hours. Concentrate the solution under reduced pressure to saturation, pour out the concentrated solution and let it cool for crystallization for 6 hours, then filter out the crystals, rinse with 20mL of dichloromethane below 10°C, recover the lotion, and then rinse with 50mL of deionized water at 30°C Drying after washing to obtain the crude product of phenethyl caffeate;

[0019] Take 5g of the above crude phenethyl caffeate, add it to 30mL of toluene, heat it to 75°C and melt it, then pour it out while it is hot and let it cool for crystallization for 6 hours, then filter out the crystals and dry them to obtain the pure phenethyl caffeate. Yield≧88.6%, purity≧97.9% (HPLC).

Embodiment 2

[0021] Take 10g of caffeic acid, stir and dissolve it in 100mLTHF and pour it into a round-bottomed flask, then add 30g of potassium bicarbonate as a catalyst, then add 9mL of β-phenylbromoethane, heat and stir at 65°C for 5 hours. Concentrate the solution under reduced pressure to saturation, pour out the concentrated solution and let it cool for crystallization for 6 hours, then filter out the crystals, rinse with 20mL of dichloromethane below 10°C, recover the lotion, and then rinse with 50mL of deionized water at 30°C Drying after washing to obtain the crude product of phenethyl caffeate;

[0022] Take 5g of the above crude phenethyl caffeate, add it to 30mL of toluene, heat it to 75°C and melt it, then pour it out while it is hot and let it cool for crystallization for 6 hours, then filter out the crystals and dry them to obtain the pure phenethyl caffeate. Yield≧88.6%, purity≧97.9% (HPLC).

Embodiment 3

[0024] Take 10g of caffeic acid, stir and dissolve it in 100mLTHF and pour it into a round-bottomed flask, then add 30g of potassium bicarbonate as a catalyst, then add 9mL of β-phenylbromoethane, heat and stir at 65°C for 5 hours. Concentrate the solution under reduced pressure to saturation, pour out the concentrated solution and let it cool for crystallization for 6 hours, then filter out the crystals, rinse with 20mL of dichloromethane below 10°C, recover the lotion, and then rinse with 50mL of deionized water at 30°C Drying after washing to obtain the crude product of phenethyl caffeate;

[0025] Take 5g of the above crude product of phenethyl caffeate, add it to 30mL of cyclohexane, heat to 75°C and melt it, pour it out while it is hot and let it cool for crystallization for 6 hours, then filter out the crystals and dry them to obtain pure phenethyl caffeate. product, yield≧88.6%, purity≧97.9% (HPLC).

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Abstract

The invention relates to a preparation method for a caffeic acid phenethyl ester. According to the preparation method, caffeic acid and beta-phenyl bromoethane react under an alkaline catalysis condition to synthesize the caffeic acid phenethyl ester. The method is simple and easy to operate, has moderate reaction conditions and small environmental pollution, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of phenethyl caffeate, which belongs to the field of drug synthesis. Background technique [0002] The main natural sources of caffeic acid phenylethyl ester (CAPE for short) are natural plants such as Rhodiola rosea and propolis, and CAPE is the main active ingredient in propolis, because it has anti-oxidation, anti-virus, anti-bacterial, anti-inflammatory, anti-arteriosclerosis, etc. It has multiple pharmacological effects, and what is more valuable is that it also has significant anti-tumor activity, so phenethyl caffeate has attracted great attention from the pharmaceutical industry. [0003] At present, there are many methods for preparing phenethyl caffeate at home and abroad, but most of them have relatively large shortcomings, which still need to be solved. Jin U et al. (Jin U, Chung T, Kang S, et al. Caffeic acid phenyl ester in propolis is inhibitor of matrix metalloproteinase-9 and invasion in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/11C07C69/732
CPCC07C67/11C07C69/732
Inventor 彭学东张梅赵金召仇家旺
Owner ZHANG JIA GANG VINSCE BIO PHARM
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