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Synthesis method of biochanin A

A technology of biochanin and a synthesis method, which is applied in the field of synthesis of biochanin A, can solve the problems of low yield and complex synthesis process, and achieve the effects of high yield, simple process and time saving

Inactive Publication Date: 2016-12-14
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a synthesis method of biochanin A, which mainly solves the problems of complex synthesis process and low yield in the prior art

Method used

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  • Synthesis method of biochanin A

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Experimental program
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Effect test

Embodiment 1

[0021] The first step: the synthesis of intermediates

[0022] In a 500 ml three-necked flask equipped with an electric stirrer, 37.8 g of anhydrous phloroglucinol, 51 g of p-methoxyphenylacetonitrile, and 100 ml of isopropyl ether were added. Start the electromagnetic stirrer at room temperature to fully stir for one hour, and then start to add 39.3 g of phosphorus oxychloride dropwise, and the dropwise addition is completed in 2 hours. After continuing to stir and react for 48 hours, slowly add 200 ml of water into the reaction liquid, reflux for 2 hours, add 2 g of activated carbon, continue to reflux for 30 minutes, and filter while hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 80 g of yellow needle-like product was obtained.

[0023] The second step: synthesis of biochanin A

[0024] Add 80 grams of the above-mentioned intermediate and 250 grams of DMF into a 500 ml three-necked reaction bottle...

Embodiment 2

[0028] The first step: the synthesis of intermediates

[0029] In a 250 ml three-necked flask equipped with an electric stirrer, 18.9 g of anhydrous phloroglucinol, 25.5 g of p-methoxyphenylacetonitrile, and 50 ml of isopropyl ether were added. Start the electromagnetic stirrer at room temperature and stir thoroughly for one hour, then start to drop 19.5 g of phosphorus oxychloride, and finish the dropwise addition in 2 hours. After continuing to stir and react for 48 hours, slowly add 100 ml of water into the reaction liquid, reflux for 2 hours, add 2 g of activated carbon, continue to reflux for 30 minutes, and filter while hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 38 g of yellow needle-like product was obtained.

[0030] The second step: synthesis of biochanin A

[0031] Add 38 grams of the above-mentioned intermediate and 125 grams of DMF into a 250 ml three-necked reaction bottle, add 52 gr...

Embodiment 3

[0035] The first step: the synthesis of intermediates

[0036] In a 1000 ml three-necked flask equipped with an electric stirrer, 76 g of anhydrous phloroglucinol, 103 g of p-methoxyphenylacetonitrile, and 200 ml of isopropyl ether were added. Start the electromagnetic stirrer at normal temperature to fully stir for one hour, then start to add 80 g of phosphorus oxychloride dropwise, and the dropwise addition is completed in 2 hours. After continuing to stir and react for 48 hours, slowly add 400 ml of water into the reaction solution, reflux for 2 hours, add 4 g of activated carbon and continue to reflux for 30 minutes, and filter while it is hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 156 g of yellow needle-shaped product was obtained.

[0037] The second step: synthesis of biochanin A

[0038] Add 156 grams of the above-mentioned intermediate and 500 grams of DMF into a 1000 ml three-necked rea...

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Abstract

The invention provides a synthesis method of biochanin A. The synthesis method includes: under room temperature, adding phosphorus oxychloride into phloroglucinol, 4-Methoxybenzyl cyanide and isopropyl ether, performing hydrolysis after reaction is completed, and decoloring with activated carbon to obtain an intermediate; allowing the obtained intermediate and methylsufonyl chloride to generate crude products of the biochanin A in DMF (dimethyl formamide) in a ring-closing manner; performing recrystallization on the obtained crude products of the biochanin A by adopting ethyl alcohol and decoloring with the activated carbon to obtain the biochanin A. The synthesis method is simple in process, low in cost, timesaving, high in yield, low in equipment corrosiveness and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of biochanin A. Background technique [0002] Biochanin A (Biochanin A, BCA) is an oxymethylated isoflavone compound, also known as chickpein A, 4'-methoxy-5,7-dihydroxyisoflavone, widely present in some Among edible plants, such as soybeans, red clover, alfalfa, peanuts and chickpeas, red clover has the highest content, but it is only 833mg / 100g. The molecular structure of BCA is similar to that of animal estrogen, and it can competitively bind to estrogen receptors to exert estrogen-like effects. It is an important phytoestrogen and has many beneficial effects on human and animal health. Prevention and treatment of osteoporosis, menopausal syndrome and other diseases. In addition, it also has various pharmacological effects such as anti-tumor, anti-inflammatory, antibacterial, hypoglycemic, anti-oxidant, and neuroprotective. However, since chi...

Claims

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Application Information

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IPC IPC(8): C07D311/36
CPCC07D311/36
Inventor 郭文华赵景辉肖金霞肖红王晓莹张瑜
Owner SHAANXI JIAHE PHYTOCHEM
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