Preparation process of polyhydroxy isoflavone

A technology of hydroxy isoflavone and trihydroxy isoflavone, which is applied in the field of preparation technology of polyhydroxy isoflavone, can solve the problem that there is no economical and efficient laboratory research synthesis technology, no mass production preparation technology report, and inability to realize mass production preparation and other problems, to achieve the effects of high yield and purity, simple and efficient carbon-enhancing and cyclization process, and easy industrial production.

Active Publication Date: 2014-11-19
中国人民解放军第三军医大学军事预防医学院
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has a short route and simple operation, the yield is also very low (8%), and the raw materials are expensive and difficult to obtain, so it is impossible to realize industrialized mass production and preparation
[0005] In summary, the preparation of 4',6,7-trihydroxyisoflavone (T2) and 3',4',6,7-tetrahydroxyisoflavone (T3) has not yet been economically and efficiently synthesized in the laboratory process, and there is no relevant mass production preparation process report

Method used

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  • Preparation process of polyhydroxy isoflavone
  • Preparation process of polyhydroxy isoflavone
  • Preparation process of polyhydroxy isoflavone

Examples

Experimental program
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Effect test

Embodiment 14

[0041] Embodiment 14', the preparation of 6,7-trihydroxyisoflavones (T2)

[0042]

[0043] 1. Preparation of 2,4`-dihydroxy-4,5-dimethoxydeoxybenzoin (compound 3)

[0044] 2kgZnCl 2 Add it into 6L of 1,4-dioxane solution, stir and disperse it, and feed 1.6 kg of HCl gas within 6 hours, then stop the feeding of HCl gas, and add 2 kg of p-hydroxybenzonitrile (compound 1) in batches under vigorous stirring, Add 2kg of 3,4-dimethoxyphenol (compound 2) after 6 hours of reaction, stop stirring after 36 hours at room temperature, add the reaction solution to 100L 5% HCl solution at 85°C for 2 hours and precipitate a large amount of light yellow precipitate, filter and wash with hot water Precipitate to neutrality, dry and weigh the product—2,4`-dihydroxy-4,5-dimethoxydeoxybenzoin (compound 3) 3.175kg, yield 85%, purity 96% (HPLC); melting point (mp): 174~175.5℃; 1 H NMR (400MHz, DMSO) δppm: 12.50 (1H, s, 2-OH), 9.32 (1H, s, 4′-OH), 7.42 (1H, s, 6-H), 7.09, 7.11 (2H, d ,J=8.6Hz...

Embodiment 23

[0049] Embodiment 23', 4', the preparation of 6,7-tetrahydroxyisoflavone (T3)

[0050]

[0051] 1. Preparation of 2-hydroxy-3`,4`,4,5-tetramethoxydeoxybenzoin (compound 6)

[0052] 1kg ZnCl 2 Add it into 3.5L of 1,4-dioxane solution, stir and disperse, and feed 0.7kg of HCl gas within 6h, then stop feeding of HCl gas, and pour 1.15kg of 3,4-dimethoxyphenylacetonitrile (compound 5) Add it in batches, add 1 kg of 3,4-dimethoxyphenol (compound 2) in batches after 6 hours of reaction, stop stirring after 36 hours at room temperature, add the reaction solution to 50L 5% HCl solution at 85°C for 2 hours for hydrolysis A large number of light yellow precipitates were precipitated, filtered and washed with hot water until neutral, dried and weighed to obtain the product 2-hydroxy-3`,4`,4,5-tetramethoxydeoxybenzoin (compound 6) 1.768kg, yield 82 %, purity 97% (HPLC), melting point 136.9-137.7°C, 1 H-NMR(DMSO,400MHz)δ(ppm):3.682-3.711(d,6H,J=11.6Hz,O-CH3),3.761(s,3H,O-CH3),3.813(s...

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Abstract

The invention relates to a preparation method of polyhydroxy isoflavone. The polyhydroxy isoflavone comprises 4',6,7-trihydroxy isoflavone and 3',4',6,7-tetrahydroxy isoflavone. According to the invention, the large-scale preparation of 4',6,7-trihydroxy isoflavone and 3',4',6,7-tetrahydroxy isoflavone can be realized by treating cheap and easily-acquired chemical raw materials including 3,4-dimethoxy phenol, 3,4-dimethoxy benzyl cyanide and hydroxybenzyl cyanide as starting materials through optimal research on Hoesch reaction, carburization n-cyclohexylmaleimide reaction and demethylation protection. The preparation method of polyhydroxy isoflavone disclosed by the invention is economic, efficient, environment-friendly, safe and easy to industrialize. The 4',6,7-trihydroxy isoflavone and the 3',4',6,7-tetrahydroxy isoflavone can be applied to the research and the development of new medicines in the aspects of medicines, food hygiene and the like.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, in particular to a preparation process of polyhydroxy isoflavones. Background technique [0002] Isoflavones are an important non-nutrient component in soybeans, and early studies have shown that they have significant anti-cancer effects (Steemas A, et al. Environ Toxicol Pharmacol, 1999, 7(3), 209-211). Studies at the molecular level have confirmed that isoflavones have the effect of inhibiting the growth and reproduction of breast cancer, prostate cancer, liver cancer and gastric cancer cell lines (Lamartiniere CA, et al. Chemoprevents Mammary Cancer, 1995, 208, 120-120.; Park JH, Oh EJ, Choi YH, et al. Int J Oncol, 2001, 18(5), 997-1002). Epidemiological surveys show that the incidence of breast cancer, prostate cancer and rectal cancer in western developed countries is 4-10 times that of developing countries (such as China, South Korea and Japan) where soybean is one of the staple foods (Su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36
Inventor 李蓉阳章友刘晶罗圣霖马婷郝玉徽任泂
Owner 中国人民解放军第三军医大学军事预防医学院
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