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Synthetic method for equol

A synthesis method and equol technology are applied in the field of organic compound preparation process improvement, can solve problems such as being unsuitable for industrial scale-up production, increase production cost, and be expensive, and achieve the effects of short synthesis steps, reduced total cost, and low price.

Inactive Publication Date: 2016-07-20
王靖林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this synthesis method are easy to obtain, and the synthesis steps are relatively short, but more expensive reagents are involved in the reaction, which increases the production cost, and the operation is complicated, so it is not suitable for industrial scale-up production

Method used

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  • Synthetic method for equol
  • Synthetic method for equol
  • Synthetic method for equol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1) Preparation of compound (B)

[0038] Put 50g (0.1968mol) of daidzein, 300g of 1,2-dichloroethane, 95g (0.9314mol) of acetic anhydride and 12g of concentrated sulfuric acid into a washed and dried 1000ml reaction flask. After the injection is completed, the temperature is raised to 60°C for 4 hours. After the reaction is completed, 1,2-dichloroethane is recovered under reduced pressure. After the recovery is completed, the residue is added back to the ice-water mixture, and a large amount of crystals are precipitated. Filtered and dried to obtain a White solid 55g. That is compound (B). Yield: 82.66% (calculated based on compound A). Melting point: 187.2-187.4°C, ESI (M / Z): 338.

[0039] 2) Preparation of compound (C)

[0040] Put 6g of 5% Pd / C, 200g of N,N-dimethylformamide, 2g (0.0196mol) of acetic anhydride and 20g (0.0592mol) of compound (B) into a washed and dried 500ml autoclave, and seal the autoclave , start stirring, after nitrogen gas exchange, fill wit...

Embodiment 2

[0046] 1) Preparation of compound (B)

[0047] Put 50g (0.1968mol) of daidzein, 300g of 1,2-dichloroethane, 95g (0.9314mol) of acetic anhydride and 12g of concentrated sulfuric acid into a washed and dried 1000ml reaction flask. After the injection is completed, the temperature is raised to 85°C for 2 hours. After the reaction is completed, 1,2-dichloroethane is recovered under reduced pressure. After the recovery is completed, the residue is added back to the ice-water mixture, and a large number of crystals are precipitated. Filtered and dried to obtain a White solid 55.53g. That is compound (B). Yield: 83.46% (calculated as compound A). Melting point: 187.1-187.4°C, ESI (M / Z): 338.

[0048] 2) Preparation of compound (C)

[0049] Put 15g of 1% Pd / C, 240g of N,N-dimethylformamide, 2g (0.0196mol) of acetic anhydride and 20g (0.0592mol) of compound (B) into a washed and dried 500ml autoclave, and seal the autoclave , start stirring, after nitrogen gas exchange, fill with ...

Embodiment 3

[0055] 1) Preparation of compound (B)

[0056] Put 50g (0.1968mol) of daidzein, 300g of 1,2-dichloroethane, 95g (0.93213mol) of acetic anhydride and 12g of concentrated sulfuric acid into a washed and dried 1000ml reaction flask. After the injection, the temperature was raised to 75°C for 3 hours. After the reaction was completed, 1,2-dichloroethane was recovered under reduced pressure. After the recovery was completed, the residue was added back to the ice-water mixture, and a large amount of crystals were precipitated. Filtered and dried to obtain a White solid 55.98g. That is compound (B). Yield: 84.15% (calculated as compound A). Melting point: 187.1-187.3°C, ESI (M / Z): 338.

[0057] 2) Preparation of compound (C)

[0058] Put 2g of 10% Pd / C, 160g of N,N-dimethylformamide, 2g (0.0196mol) of acetic anhydride and 20g (0.0592mol) of compound (B) into a washed and dried 500ml autoclave, and seal the autoclave , start stirring, after nitrogen gas exchange, fill with H 2 T...

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Abstract

The invention provides a synthetic method for equol. The synthetic method comprises the following steps: with daidzein as a raw material, subjecting daidzein to an esterification reaction to obtain a compound B; subjecting the compound B to olefinic-bond conjugation and a reduction reaction of a carbonyl group so as to obtain a compound C; subjecting the compound C to a dehydration reaction so as to obtain a compound D; and carrying out double-bond hydrogenation on the compound D so as to obtain equol. The synthetic method provided by the invention has the advantages of short synthesis steps, simple operation, economic performance, environmental protection, yield of 70% or above in each step, obviously increased overall yield and suitability for industrial mass production.

Description

technical field [0001] The invention relates to the improvement of the preparation process of organic compounds, in particular to the improvement of the synthesis process of daidzein metabolite-equol. Background technique [0002] In recent years, the biological effects of soybean isoflavones (soybean isoflavones, SI) have attracted great attention. Studies have found that soybean isoflavones, mainly composed of daidzein (Dai) and genistein (Gen), have a wide range of biological properties, such as estrogen-like effects, anti-oxidation, cell cycle regulation, etc. , can prevent a variety of diseases that seriously plague human health, including osteoporosis, Alzheimer's disease (AD), arteriosclerosis, and breast cancer, prostate cancer, etc. With further research, it was found that the metabolite equol (equol, Eq) of daidzein has higher biological characteristics, and the biological effect of SI may be attributed to its metabolite Eq to some extent. The structural formula ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58
Inventor 王靖林刘桂贞于瑞梅魏兆民穆振强张荣荣
Owner 王靖林
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