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Synthetic method of apigenin

A synthesis method and technology of apigenin, applied in the direction of organic chemistry and the like, can solve the problems of unsuitable large-scale industrial production, harsh production conditions and high cost of apigenin, and achieve the effects of stable reaction, high equipment utilization rate and low production cost.

Inactive Publication Date: 2014-09-10
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It mainly solves the problems that the cost of preparing apigenin by the existing method is high, the production conditions are bad, and it is not suitable for large-scale industrial production

Method used

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preparation example Construction

[0022] The synthetic method of this apigenin comprises following synthetic route and step:

[0023]

[0024] Concrete technical scheme of the present invention is as follows:

[0025] 1] Condensation reaction (i.e. preparation of ethyl p-hydroxyphenylacetoacetate)

[0026] The key intermediate ethyl p-hydroxyphenylacetoacetate was prepared by condensation of p-hydroxyacetophenone and diethyl carbonate under alkaline conditions. Wherein the basic catalyst refers to strong basic catalysts such as sodium, sodium alkoxide, sodium hydride, sodium tert-butoxide, potassium tert-butoxide; preferred catalyst is sodium alkoxide; reaction solvent is benzene, toluene, ether, tetrahydrofuran, dehydrated alcohol, without water methanol etc. Preferred solvents are toluene, absolute ethanol or absolute methanol.

[0027] The specific operation process is:

[0028] Feed in the reaction bottle, p-hydroxyacetophenone, reaction solvent and basic catalyst, add diethyl carbonate solution dro...

example 1

[0035] Example 1 Feed into the reaction flask, 68g of p-hydroxyacetophenone, 160ml of anhydrous methanol, stir to dissolve, add 9g of sodium methoxide, after stirring evenly, slowly add 36g of diethyl carbonate dropwise at room temperature, about 2h to complete the dropwise addition. After dripping, the temperature was raised to reflux, and after about 7 hours, the reaction was stopped. The solvent was recovered under reduced pressure until nearly dry. Cool down to room temperature, add water, stir evenly, separate liquids, and dry over anhydrous sodium sulfate to obtain 59.5 g of the product (yield 82%).

example 2

[0036] Example 2 Feed into the reaction flask, diethyl carbonate 34g, anhydrous methanol 80ml, stir evenly, add sodium methoxide 12g, at room temperature, add dropwise (p-hydroxyacetophenone 68g+80ml) solution, drop about 3h. After the addition, the temperature was raised to reflux, and after about 8 hours, the reaction was stopped. The solvent was recovered under reduced pressure until nearly dry. Cool down to room temperature, add water, stir evenly, separate liquids, and dry over anhydrous sodium sulfate to obtain 56 g of the product (yield 78%).

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Abstract

The invention relates to a synthetic method of apigenin. The method mainly comprises two steps of preparing para hydroxybenzene ethyl acetoacetate and preparing apigenin. The synthetic method disclosed by the invention is mainly used for solving the problems that an existing method for preparing apigenin is relatively high in cost and poor in production condition, and is not suitable for large-scale industrial production. The synthetic method of apigenin is simple in route, cheap in raw material and rich in source, and is used for chemically synthesizing apigenin.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a chemical synthesis method of natural product apigenin. Background technique [0002] Apigenin, also known as apigenin, the system name is 5,7,4'-trihydroxyflavone, and the structure of the English name Apigenin is: [0003] [0004] Apigenin is widely found in a variety of fruits, vegetables, beans and tea leaves, Scrophulariaceae plants, Scrophulariaceae plants, Polygonum cuspidatum, Liliaceae Veratrum, and Pinaceae plants, among which celery has the highest content. [0005] Apigenin has many pharmacological effects, such as anti-tumor, anti-oxidation, anti-inflammatory, and sedative effects, among which its anti-tumor effect is the most prominent. Compared with other flavonoids (quercetin, kaempferone), apigenin has the characteristics of low toxicity and no mutagenicity. Although apigenin widely exists in many kinds of fruits and vegetables, its content in natural product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 肖金霞靳莎杨雪峰郭文华
Owner SHAANXI JIAHE PHYTOCHEM
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