Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing caffeic acid ester derivatives

A technology of caffeic acid and derivatives, which is applied in the field of medicine and chemical industry, can solve the problems of cumbersome feeding or reaction operation, difficulty in product separation and purification, and weak generality of the method, and is beneficial to laboratory synthesis and large-scale production application, reaction Universal and easy-to-control effects

Inactive Publication Date: 2014-07-16
SHANGHAI JIAO TONG UNIV
View PDF4 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] The above-mentioned existing preparation methods have their own characteristics, but all have one or more of the following defects: use of corrosive or difficult-to-obtain chemical raw materials; more waste discharge, unfriendly environment; long reaction time, low yield and Unstable; feeding or reaction operation is cumbersome; product separation and purification is difficult; the method is not universal, and the yield varies greatly with the structure of the substrate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing caffeic acid ester derivatives
  • Method for preparing caffeic acid ester derivatives
  • Method for preparing caffeic acid ester derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of Caffeic Acid Phenylethyl Ester

[0041]

[0042] Mix 1.0 g (1.0 equivalent) of caffeic acid, 678 mg (1.0 equivalent) of phenylethyl alcohol, 1 mol% trifluoromethanesulfonate with 125 mL of solvent, place in a hot bath at 120°C and stir for 40 minutes, remove the hot bath, and wait After reaching room temperature, wash with 30 mL of pure water and 30 mL of 2% wt sodium bicarbonate solution, and dry over anhydrous sodium sulfate. Add 0.5 g of activated carbon, stir at 80° C. for 30 minutes, filter, and concentrate to obtain a crude product.

[0043] The crude product was subjected to column chromatography to obtain a white solid product (758 mg, 48.0%). Mp128‐130℃; IR(KBr)ν max 3480,3328,1683,1601,1362,1301,1279,1182cm ‐1 ; 1 H NMR (400MHz, DMSO‐d 6 )δ H 7.46 (1H, d, J = 16Hz, C H =CHCO),7.34‐7.18(5H,m,CH 2 CH 2 C 6 h 5 ), 7.05 (1H, s, 2‐ArH), 6.99 (1H, d, J=8.0Hz, 6‐ArH), 6.77 (1H, d, J=8.0Hz, 5‐ArH), 6.24 (1H, d , J=16Hz, CH=C H CO),4.32(2H,...

Embodiment 2

[0045] Preparation of Caffeic Acid Phenylpropanol Ester

[0046]

[0047] Operation steps with reference to embodiment 1.

[0048] The crude product obtained in this example was subjected to column chromatography to obtain a white solid product (787mg, 47.5%). Mp122‐124℃; IR(KBr)ν max 3495,3338,1683,1638,1602,1278,1184cm ‐1 ; 1 H NMR (400MHz, DMSO‐d 6 )δ H 7.47 (1H, d, J = 16Hz, C H =CHCO),7.32‐7.13(5H,m,CH 2 CH 2 CH 2 C 6 H 5 ), 7.07 (1H, s, 2‐ArH), 7.01 (1H, d, J=8.0Hz, 6‐ArH), 6.78 (1H, d, J=8.0Hz, 5‐ArH), 6.27 (1H,d , J=16Hz, CH=C H CO),4.10(2H,t,J=6.8Hz,OC H 2 ),2.67(2H,t,J=7.6Hz,C H 2 C 6 h 5 ),1.93(2H,m,CH 2 C H 2 CH 2 ) ppm; 13 C NMR (100MHz, DMSO‐d 6 )δ C HRMS‐ESI C 18 h 18 o 4 Measurement [M‐H] ‐ 297.1127, measured 297.1135.

Embodiment 3

[0050] Preparation of phenylethyl cinnamate

[0051]

[0052] Mix 1.0 g (1.0 equivalent) of cinnamic acid, 824 mg of phenylethyl alcohol (1.0 equivalent), 1.66 mol% trifluoromethanesulfonate with 100 mL of solvent, stir in a hot bath at 120 ° C, and reflux for 2 hours and 4 hours, respectively. Add 1.66 mol% trifluoromethanesulfonate (a total of 5 mol% trifluoromethanesulfonate was added) at the time of 1 hour, and then remove the hot bath after reflux for 2 hours. After cooling to room temperature, add 30mL pure water and 30mL 2% carbonic Washed with sodium hydrogen solution, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product.

[0053] The crude product was crystallized in petroleum ether to obtain a white solid product (1630mg, 95.8%). Mp50‐52℃; 1 H NMR (400MHz, CDCl 3 )δ7.74‐7.68(2H,m,2,6‐ArH),7.64(1H,d,J=16Hz,C H = CHCO), 7.42 (3H, m, 3, 4, 5‐ArH), 7.35‐7.19 (5H, m, 2', 3', 4', 5', 6'‐ArH), 6.62 (1H, d , J=16Hz, CH=C H CO),4.36(2H,t,J=...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing caffeic acid ester derivatives in the technical field of pharmaceutical chemicals. The method comprises the steps that metal trifluoromethanesulfonate is used as a Lewis acid catalyst, mixed with caffeic acid, alcohol and solvent and then subjected to an esterification reaction under a mild condition, and then a crude product is obtained; the crude product is purified, and then the caffeic acid ester derivatives are obtained. According to the method, the caffeic acid or an analogue of the caffeic acid and the alcohol are used as reaction raw materials to obtain target molecules in one step, and multiple reaction steps or operation steps are abandoned; since the metal trifluoromethanesulfonate is used as the Lewis acid catalyst for catalysis, various caffeic acid ester compounds are synthesized under general conditions, the production cycle is shortened, and a complex operation process is simplified; regarding recovery of the catalyst and the organic solvent, production cost is lowered, and emission of waste is reduced.

Description

technical field [0001] The invention relates to a method in the technical field of medicine and chemical engineering, in particular to a method for preparing caffeic acid ester derivatives. Background technique [0002] Caffeic acid and its derivatives have various important pharmacological effects such as anti-oxidation, anti-inflammatory, analgesic, immune regulation, antibacterial, antiviral, and hypoglycemic. It has good application prospects in the prevention and treatment of oxidative stress and inflammatory response-related diseases, and further research is also expected to provide new therapeutic strategies for cardiovascular diseases, cancer, human immunodeficiency virus infection, diabetes and other diseases. Caffeic acid esters are an important part of caffeic acid derivatives. With the continuous revelation of the biological effects of caffeic acid esters, especially caffeic acid phenylethyl alcohol ester (CAPE), more and more caffeic acid ester compounds have be...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C69/732C07C69/618C07C69/65C07C69/734C07C67/08C07C205/42C07C201/12C07C255/55C07C253/30A61P35/00
CPCC07C67/08C07C69/618C07C69/65C07C69/732C07C69/734C07C201/12C07C205/42C07C253/30C07C255/55C07C2601/14Y02P20/582
Inventor 傅磊谢东升杨凤志谢谨张曼
Owner SHANGHAI JIAO TONG UNIV