Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of fisetin

A synthetic method, the technology of fisetin, applied in the direction of organic chemistry, etc., can solve the problems that the product yield and content cannot be obtained at the same time, and the synthesis of fisetin is only suitable, so as to reduce the felling of boxwood, low production cost, and easy operation. simple effect

Inactive Publication Date: 2019-03-29
SHAANXI JIAHE PHYTOCHEM
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to solve the deficiency that the synthesis of fisetin in the prior art is only suitable for the laboratory, and the product yield and content cannot be combined, and provides a synthetic method for fisetin suitable for industrialization, so as to ensure the product yield. Rate and content are guaranteed

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
  • Synthesis method of fisetin
  • Synthesis method of fisetin
  • Synthesis method of fisetin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A synthetic method for fisetin, comprising the following steps:

[0053] Step 1) Produces a white mixture

[0054] 1.1) Stir 100ml of 2-butanone and 24g of benzyl chloride evenly, then add 8g of 2,4-dihydroxyacetophenone and 25g of anhydrous K 2 CO 3 , stirring, after heating and reflux reaction for 12h, add 100ml of water and stir;

[0055] 1.2) After the reaction is finished, extract with dichloromethane, evaporate the solvent by rotary evaporation, and collect the residue; and recrystallize the residue with 20ml of methanol to obtain 13.6g of white mixture powder with a yield of 75.1%.

[0056] Step 2) generate 3', 4'-dihydroxy-7-benzylchalcone

[0057] 2.1) Dissolve 13.6g of white mixture powder and 13.5g of protocatechualdehyde into 100ml of absolute ethanol, add 120g of potassium hydroxide solution with a mass concentration of 30%, stir under nitrogen protection, heat up and reflux for about 20h , cooled and poured into 150g of ice water to quench the reaction...

Embodiment 2

[0067] A synthetic method for fisetin, comprising the following steps:

[0068] Step 1) Produces a white mixture

[0069] 1.1) Stir 120ml of 2-butanone and 29g of benzyl chloride evenly, then add 9.6g of 2,4-dihydroxyacetophenone and 30g of anhydrous K 2 CO 3 , after heating up to reflux for 12 hours, add 121ml of water and stir;

[0070] 1.2) After the reaction is finished, extract with dichloromethane, evaporate the solvent by rotary evaporation, and collect the residue; and recrystallize the residue with 20ml of methanol to obtain 15.6g of white mixture powder with a yield of 75.1%.

[0071] Step 2) generate 3', 4'-dihydroxy-7-benzylchalcone

[0072] 2.1) Dissolve 15.6g of white mixture powder and 15.5g of protocatechualdehyde into 120ml of absolute ethanol, add 150g of potassium hydroxide solution with a mass concentration of 30%, and stir and heat up to reflux for about 20h under nitrogen protection. Cool and pour into 180g of ice water to quench the reaction;

[007...

Embodiment 3

[0082] A synthetic method for fisetin, comprising the following steps:

[0083] Step 1) Produces a white mixture

[0084] 1.1) Stir 50ml of 2-butanone and 12g of benzyl chloride evenly, then add 4g of 2,4-dihydroxyacetophenone and 13g of anhydrous K 2 CO 3 , after heating and reflux reaction for 12h, add 50ml of water and stir;

[0085] 1.2) After the reaction is finished, extract with dichloromethane, evaporate the solvent by rotary evaporation, and collect the residue; and recrystallize the residue with 20ml of methanol to obtain 6.5g of white mixture powder with a yield of 74.5%.

[0086] Step 2) generate 3', 4'-dihydroxy-7-benzylchalcone

[0087] 2.1) Dissolve 6.5g of white mixture powder and 6.5g of protocatechualdehyde into 50ml of absolute ethanol, add 60g of potassium hydroxide solution with a mass concentration of 30%, and stir and heat up to reflux for about 20h under nitrogen protection. Cool and pour into 80g of ice water to quench the reaction;

[0088] 2.2) ...

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 provides a synthesis method of fisetin, and solves the problems that the existing fisetin synthesis method is only applicable to laboratories, and the product yield and the content cannot be both obtained. The synthesis method comprises the following steps that 1,2-butanone, benzyl chloride, 2,4-dihydroxyacetophenone and anhydrous K2CO3 are used for generating an intermediate productwith protection groups; 2, under the nitrogen gas protection and in an alkaline environment, the intermediate product and protocatechualdehyde generate condensation reaction to generate 3',4'-dihydroxy-7-benzylchalcone; 3, the 3',4'-dihydroxy-7-benzylchalcone is reduced to generate 3',4',7-trihydroxychalcone; 4, the 3',4',7-trihydroxychalcone is put into the alkaline environment for hydroxy addition; then, cyclization reaction is performed under the para-toluenesulfonic acid catalysisto obtain the fisetin. The synthesis method can be used for industrial production; the synthesis method has the advantages that the operation is simple; raw materials can be easily obtained; the production cost is relatively low; the yield and the purity of the obtained intermediate product and the final product are relatively high; relatively good development prospects are realized.

Description

technical field [0001] The invention belongs to raw material medicine synthesis technology, in particular to a synthesis method of fisetin. Background technique [0002] Fitetin is a flavonoid substance with a CAS number of 528-48-3 and molecular formula C 15 h 10 o 6 , molecular weight 286.23, molecular structure formula: [0003] [0004] Fisetin (FIS), also known as fisetin, buterin, fisetin, 3,3',4',7-tetrahydroxyflavone, fisetin. The pure product is yellow needle crystal, melting point 330°C (decomposition), soluble in ethanol, acetone and acetic acid, almost insoluble in water, ether, benzene, chloroform and petroleum ether. [0005] Fisetin is a kind of natural flavonoid alcohol compound extracted from plants such as Anacardiaceae wood wax tree, the content in boxwood is 0.8-2%; it also exists in vegetables and fruits, such as apples, persimmons, grapes , kiwi, strawberry, onion and cucumber etc. [0006] Fisetin has pharmacological characteristics such as an...

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 Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 郭文华肖金霞张瑜赵景辉
Owner SHAANXI JIAHE PHYTOCHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap 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