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Preparation method of (S)-equol

A technology of equol and compound, applied in the field of preparation of -equol, can solve problems such as complicated operation, and achieve the effects of simple operation, cost reduction and low price

Inactive Publication Date: 2012-08-15
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The present invention will solve the problem of complex operation of the existing method for preparing (S)-equol, and provide a preparation method of (S)-equol

Method used

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  • Preparation method of (S)-equol
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  • Preparation method of (S)-equol

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specific Embodiment approach 1

[0032] Specific embodiment one: the preparation method of a kind of (S)-equol of the present embodiment is carried out according to the following steps:

[0033] 1) Preparation of Compound A

[0034] 1. Add daidzein, acetic anhydride and solvent into the reaction bottle, stir evenly at a speed of 100-300r / min, then add sulfuric acid with a mass percentage of 98%, and then heat to 70°C-150°C and reflux for 3- 6h to obtain the reaction solution; 2. Add distilled water at 0°C to 4°C to the reaction solution in step 1, and stir evenly at a speed of 100 to 300r / min to obtain a solid-liquid mixture; 3. Mix the solid-liquid mixture obtained in step 2 Filter the mixture, collect the solid phase, mix and recrystallize according to the ratio of solid phase to solvent mass volume ratio of 1g: 1-5mL, then cool at a temperature of 5-10°C for 10-30min, and filter and collect the obtained The solid phase is dried at 50°C for 4-8 hours to obtain compound A; wherein, the molar ratio of daidze...

specific Embodiment approach 2

[0045] Specific embodiment two: the difference between this embodiment and specific embodiment one is: the solvent described in the preparation of step 1) compound A and step 3) the preparation of compound C is DMF, 1,2-dichloroethane, DMSO or toluene. Other steps and parameters are the same as those in Embodiment 1.

specific Embodiment approach 3

[0046] Embodiment 3: This embodiment is different from Embodiments 1 to 2 in that: step 1) in the preparation of compound A, the molar ratio of daidzein and acetic anhydride is 1:3. Other steps and parameters are the same as those in Embodiments 1 to 2.

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Abstract

The invention relates to a preparation method of (S)-equol, which aims to solve the problem of complex operation in the existing preparation method of (S)-equol. The preparation method comprises the following steps: by using daidzein as the main material, carrying out hydroxy protection, catalytic hydrogenation, dehydration and chiral catalytic reduction to prepare the (S)-equol. The invention has the advantages of cheap and accessible raw materials and low cost, is simple to operate, and is suitable for industrial scale-up production; and the yield is 60-70%. The invention is applicable to the field of synthesis of medicine compounds.

Description

technical field [0001] The present invention relates to a preparation method of (S)-equol, in particular to a kind of (S)-3,4-dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyridine Preparation method of furan-7-ol [(S)-equol]. Background technique [0002] (S)-3,4-dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol [(S)-equol, (S)-equol] has anti Tumors, relief of menopausal syndrome, prevention of osteoporosis, reduction of cardiovascular morbidity and effective treatment of male hair loss and other effects. The research on its anti-cancer effect currently focuses on cancers related to sex hormones such as prostate cancer and breast cancer, among which the inhibitory effect of equol on prostate cancer has been confirmed by epidemiology and in vitro. Its structural formula is as follows: [0003] [0004] (S)-equol [0005] The preparation method of equol mainly contains following two kinds: [0006] The synthetic route of method one racemic equol is as follows: [0007] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58
Inventor 张华史成阳迟帅鲁国明王阳李强苑兰兰
Owner HEILONGJIANG UNIV
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