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Synthesis method of resveratrol and derivatives thereof

A technology of resveratrol and its synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, chemical/physical processes, etc., and can solve the problem of low reactivity, resveratrol double bond breakage, molecular sieve solid acid catalyst activity and unsuitable reaction conditions, etc., to achieve the effects of high product selectivity, easy separation and recovery, and good application value

Active Publication Date: 2011-06-15
GREAT FOREST BIOMEDICAL LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the patent (CN: 86104272A, 1986), Xu Peiling et al. used sulfuric acid to selectively crack trimethyl gallate and demethylated it. However, sulfuric acid was used as a demethylating agent with low reactivity and could only be used with some methyl ethers with special structures. Base ether reaction; Wen Yongju et al. (Jiangsu Agricultural Science, 2010, 2: 322-323) used hydrobromic acid and acetic acid solution to thermally crack emodin methyl ether to demethylate it. This type of method requires more severe conditions , may cause some sensitive structures to decompose or change, and easily break the double bond in the molecular formula of resveratrol and its derivatives
[0015] It has been reported in the literature that the hydrolysis reaction of ethers using molecular sieve solid acid catalysts usually requires high temperature and high pressure gas phase reaction conditions, while resveratrol and resveratrol derivatives have a special structure of trans intramolecular double bonds, and generally molecular sieve solids The acid catalyst activity and reaction conditions are not suitable for the hydrolysis reaction of such substances

Method used

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  • Synthesis method of resveratrol and derivatives thereof
  • Synthesis method of resveratrol and derivatives thereof
  • Synthesis method of resveratrol and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Dissolve 13.5g (0.05mol) resveratrol trimethyl ether (compound II-a) in a mixed solution of 250mL DMSO and 2mL deionized water, stir and heat to 75°C, and fix the GL-5 solid acid catalyst The bed reactor was heated to 170°C. The reaction solution was continuously added to a 1.5m fixed-bed reactor at a rate of 1mL / min, and the effluent was collected in an Erlenmeyer flask. After the collection, 25mL of distilled water was added, stirred for about 30min to cool down, left to stand to precipitate crystals, filtered (the filtrate was evaporated to remove methanol and water Afterwards, it can be recycled), the filter cake is 11.0g, recrystallized with 18mL 50% ethanol aqueous solution, and obtains white crystal 10.7g, namely resveratrol (compound I-a), yield (in the amount of compound II-a substance Count) is 93.9%.

[0041]

Embodiment 2

[0043] Dissolve 18.9g (0.07mol) of compound II-a in a mixed solution of 300mL DMSO and 3mL deionized water, stir and raise the temperature to 75°C, and raise the temperature of the fixed-bed reactor equipped with GL-5 solid acid catalyst to 170°C. The reaction solution was continuously added to a 1.5m fixed-bed reactor at a speed of 1mL / min, and the effluent was collected in an Erlenmeyer flask. After collection, 30mL of distilled water was added, stirred for about 30min to cool, left to stand to precipitate crystals, filtered (the filtrate was evaporated to remove methanol and After water, can recycle), filter cake is 15.2g, with 25mL50% aqueous ethanol recrystallization, obtains white crystal 14.7g, namely resveratrol (compound I-a), yield (in the amount of compound II-a substance Calculated) is 92.1%.

Embodiment 3

[0045] The reaction temperature of the fixed bed was 160° C., other operations were the same as in Example 1, and the yield of resveratrol (compound I-a) was 90.7%.

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Abstract

The invention discloses a synthesis method of resveratrol and derivatives thereof, which comprises the following steps: in an organic solvent dimethyl sulfoxide or dimethyl formamide, carrying out demethylation reaction on a compound (II) and water in a fixed bed reactor filled with a GL-5 solid acid catalyst, and carrying out after-treatment on the reaction liquid to obtain the resveratrol disclosed as Formula (I) and derivatives thereof. By using the GL-5 solid acid as the catalyst, the invention has the advantages of high product selectivity and high yield; the catalyst can be easily separated from the solvent so as to be recovered, and can be repeatedly used, thereby being environment-friendly; and the invention does not use AlCl3 or BBr3, which is used in large quantities in the traditional technique and can cause severe environmental pollution, thereby reducing the emission of three wastes and having high application value.

Description

(1) Technical field [0001] The invention relates to a synthesis of natural active substances, in particular to a chemical synthesis method of resveratrol and its derivatives. (2) Background technology [0002] Resveratrol has been widely used in medicine, health care products and other fields due to its good anti-inflammatory, anti-cancer and anti-oxidation effects since its appearance. The latest research shows that resveratrol derivatives have better quality and stronger physiological activity than resveratrol. [0003] The synthetic methods of resveratrol and resveratrol derivatives reported in the literature, taking resveratrol as an example, mainly use 3,5-dihydroxybenzyl alcohol as raw material, through methylation, bromination, Arbuzov heavy The intermediate 3,5-dimethoxybenzyl phosphonate is obtained by row reaction, and then undergoes Wittig.Homer condensation reaction with anisaldehyde to obtain resveratrol trimethyl ether, and finally demethylation reaction synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/055B01J23/78
Inventor 顾海宁汪劲松李小玲徐玲
Owner GREAT FOREST BIOMEDICAL LTD