Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

A kind of synthetic method of natural product e-2,3',4,5'-tetrahydroxystilbene

A technology of tetrahydroxystilbene and natural products, applied in chemical instruments and methods, preparation of organic compounds, preparation of oxygen-containing compounds, etc., can solve problems such as difficult acquisition of raw materials, difficulty in large-scale preparation, poor atom economy, etc., to achieve The reaction conditions are green and environmentally friendly, the yield is high, and the operation is easy

Active Publication Date: 2019-09-17
GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK +1
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Regarding the synthesis of E-2,3',4,5'-tetrahydroxystilbene, there are Wittig reaction, Wittig-Horner reaction, Suzuki cross-coupling reaction and Perkin condensation reaction methods etc. in bibliographical reports, but these methods have high cost, Noble metal catalyst is required, the yield is low, the raw materials are not easy to obtain, and the hydroxyl group needs to be protected by methyl, silyl, etc. and then deprotected (Chem.Pharm.Bull.2010,58,1492-1496; Chin.J.Org.Chem.,2010 , 30, 1574-1579; Eur.J.Med.Chem., 2007, 42, 841-850; Bioorg.Med.Chem.Lett., 2006, 16, 5767-5772), poor atom economy, difficulty in large-scale preparation, etc.

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
  • A kind of synthetic method of natural product e-2,3',4,5'-tetrahydroxystilbene
  • A kind of synthetic method of natural product e-2,3',4,5'-tetrahydroxystilbene
  • A kind of synthetic method of natural product e-2,3',4,5'-tetrahydroxystilbene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0034] Put 1,3-acetonedicarboxylate dimethyl (24.36g, 140mmol) into a single-necked round bottom flask, and then throw in metallic sodium (0.28g, 12mmol), and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weighing 19.74g , yield 95%.

[0035] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0036] Add 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester (7.15g, 24mmol) into the round bottom flask, then pour 12% sodium hydroxide aqueous solution (64ml, 192mmol), and heat in an oil bath Distill at 140°C for 3h, after the reaction, cool to 80°C, add concentrated sulfuric acid (33.6ml, 240mm...

Embodiment 2

[0042] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0043] Put 1,3-acetonedicarboxylate dimethyl (24.36g, 140mmol) into a single-necked round bottom flask, and then throw in metallic sodium (0.28g, 12mmol), and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weight 19.02g , yield 91%.

[0044] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0045] Add 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester (7.15g, 24mmol) into the round bottom flask, then pour 12% potassium hydroxide aqueous solution (56ml, 120mmol), and heat in an oil bath Distill at 140°C for 3h. After the reaction, cool to 80°C, add concentrated sulfuric acid (26.9ml, 192m...

Embodiment 3

[0051] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0052] Add 60ml of methanol, sodium metal (0.28g, 12mmol) and dimethyl 1,3-acetonedicarboxylate (24.36g, 140mmol) into a single-necked round bottom flask, and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weight 10.90g , yield 52%.

[0053] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0054] Drop into 3,5-dihydroxy-2,4-dimethoxycarbonyl phenylacetic acid methyl ester (7.15g, 24mmol) in the round bottom flask, then pour cesium hydroxide (30g, 0.2mol), water (70ml), Heat in an oil bath at 140°C for distillation for 3 hours. After the reaction is complete, cool to 80°C, add concentrated sulfuric aci...

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 synthesis method of a natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene. According to the method, 1,3-acetone dicarboxylic acid dimethyl ester is used as a starting raw material; condensation and aromatization reactions are performed to obtain 3,5-dihydroxy-2,4-dicarboxylate methyl phenyl acetate; then, hydrolysis and decarboxylation are performed to obtain 3,5-dyhydroxy phenylacetic acid; the 3,5-dyhydroxy phenylacetic acid and 2,4-dihydroxy benzaldehyde take condensation reaction under the existence of alkali to obtain 3-(3,5-dihydroxy phenyl)-7-hydroxy coumarin; next, open loop decarboxylation reaction is performed under the alkaline condition; the natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene is obtained. The method has the advantages that the raw materials are easily obtained; the reaction route is simple and fast; the operation is convenient; the yield is higher.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing natural product E-2,3',4,5'-tetrahydroxystilbene. Background technique [0002] E-2,3',4,5'-Tetrahydroxystilbene (Oxyresveratrol) is a natural product isolated for the first time from Yunnan jackfruit (Artocarpus lakoocha). It is also found in Liliaceae, Liliaceae, and Gnetaceae, and is the 2'-hydroxylated derivative of the important stilbene natural product resveratrol. E-2,3',4,5'-Tetrahydroxystilbene has a variety of beneficial biological activities, such as Tyrosinase inhibition, Antioxidant, Neuroprotective, anti-inflammatory Anti-inflammatory, Hepatoprotective, Antibrowning and Anti-allergic (Bioorg.Med.Chem.Lett., 2006, 16, 5650-5653; Chem. Biol. Interact., 2016, 245, 110-121; Nitric Oxide., 2003, 9, 64-76; Biol. Pharm. Bull., 2006, 29, 2419-2424; J. Agric. Food. Chem., 2008, 56 , 4463-4468; Environ. Toxicol. Pharmacol., 2008, 26, 325-330; Arch...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/50C07C39/21C07D311/16C07C67/343C07C69/84C07C27/02C07C51/38C07C59/52
Inventor 邹永黄熙华盛剑飞宋现恒位文涛
Owner GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com