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A kind of preparation method of dihydrodaidzein

A technology of daidzein and dihydro, which is applied in the field of preparation of dihydrodaidzein, can solve the problems of insufficient economical efficiency of preparation and chemical synthesis of equol, low efficiency of fermentation and preparation, etc.

Active Publication Date: 2020-09-25
SHANDONG YUANLITAI MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the chemical synthesis of equol generally uses noble metal catalysts with chiral ligands. Because the chiral ligands are expensive and the optical activity will gradually inactivate with the number of catalysis, the economics of chemically synthesizing equol are seriously insufficient, and the product is expensive. , is also a worldwide problem hindering the commercial application of equol
[0004] For microbial fermentation, dihydrodaidzein, as an intermediate in the fermentation process for the production of equol by biological fermentation, has not been able to be prepared by chemical processes from daidzein for a long time, and the efficiency of fermentation preparation is also extremely low, which cannot meet the requirements of the fermentation process. Requirements for preparing equol from hydrogen daidzein
Therefore, the preparation of equol by fermentation can only be at the laboratory level and the fermentation efficiency is extremely low, which cannot reach the scale industrial level

Method used

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  • A kind of preparation method of dihydrodaidzein
  • A kind of preparation method of dihydrodaidzein
  • A kind of preparation method of dihydrodaidzein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] A preparation method of dihydrodaidzein, comprising the following methods:

[0101] 1. Synthetic route

[0102]

[0103] 2. Preparation process:

[0104] 1), the preparation technology of compound B:

[0105]

[0106] operate:

[0107] Install a reflux condenser on the cleaned and dried reaction bottle, and after installation, put acetic anhydride and compound A into the reaction bottle. After the casting is completed, the temperature is raised to 75-80°C under stirring, and anhydrous sodium acetate is added in batches. Control the feed rate to keep the internal temperature above 80°C. After the casting was completed, the temperature was raised to 120°C for 32 hours. After the reaction is completed, cool the reaction liquid to below 20°C, precipitate a large amount of solids, suction filter, put the solid material into 800g distilled water, heat up to 80-85°C for 2 hours, cool, suction filter, put the solid material into another 800g distilled water, and then ...

Embodiment 2

[0148] 1. Synthetic route:

[0149]

[0150] 2. Preparation process

[0151]1), the preparation method of compound F:

[0152] Preparation: Compound A: 100g (0.39mol)

[0153] Isopropyl bromide: 173g (1.4mol)

[0154] NaOH: 34.3g (0.858mol)

[0155] Absolute ethanol: 600g

[0156] operate:

[0157] Put compound A, NaOH, and absolute ethanol into the washed and dried reaction bottle, heat up to 40-50°C and stir for 60 minutes after the injection. After the reaction is complete, start to add isopropyl bromide dropwise, and control the rate of addition to keep the inner temperature of the reaction solution at 20-25°C. After the dropwise addition was completed, the temperature was raised to 70-75°C and the reaction was kept for 24 hours. After the reaction is completed, adjust the pH to 5-6 with dilute hydrochloric acid, precipitate crystals, filter with suction, and wash with water. The solid material was dried to obtain compound F. Compound F was obtained: 108.8g, mo...

Embodiment 3

[0182] 1. Synthetic route:

[0183]

[0184] 2. Preparation process:

[0185] 1), the preparation technology of compound J:

[0186] Preparation: Compound G: 34.2g (0.1mol)

[0187] p-toluenesulfonyl chloride: 22.86g (0.12mol)

[0188] Sodium bicarbonate: 42g (0.5mol)

[0189] Toluene: 200g

[0190] Distilled water: 100g

[0191] operate:

[0192] Install a reflux condenser on the cleaned and dried reaction flask. After installation, put compound G, p-toluenesulfonyl chloride, sodium bicarbonate, and toluene into the reaction flask. After the casting is completed, the temperature is raised to 105-112°C under stirring for 6 hours under reflux. A large amount of carbon dioxide gas evolved during the reaction. After the reaction is completed, cool the reaction liquid to below 40°C, add 100g of distilled water, and continue to heat up to 95°C and reflux for 2h. After the reaction is complete, cool the reaction liquid to below 20°C, let stand and separate the layers, d...

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Abstract

Disclosed in the present invention is a method for preparing dihydrodaidzein, comprising the following steps: (1) using the compound represented by formula I as a raw material for an oxidation reaction to prepare a compound represented by formula II; and (2) de-protecting the compound represented by formula II to prepare dihydrodaidzein. The method for preparing dihydrodaidzein provided in the present invention provides a low-cost, cost-effective fermentation substrate for the production of equol for large-scale industrial fermentation.

Description

technical field [0001] The invention belongs to the field of organic compound preparation, and in particular relates to a preparation method of dihydrodaidzein. Background technique [0002] Equol has the functions of anti-tumor, alleviating menopausal syndrome, preventing osteoporosis, reducing cardiovascular incidence and effectively treating male hair loss, etc. Equol, which exists in nature, is synthesized by chemical methods or microbial fermentation methods. [0003] At present, the chemical synthesis of equol generally uses noble metal catalysts with chiral ligands. Because the chiral ligands are expensive and the optical activity will gradually inactivate with the number of catalysis, the economical efficiency of chemical synthesis of equol is seriously insufficient, and the product is expensive. , is also a worldwide problem hindering the commercial application of equol. [0004] For microbial fermentation, dihydrodaidzein, as an intermediate in the fermentation p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/38C12P17/06
CPCC07D311/38C12P17/06Y02P20/55
Inventor 王靖林魏兆民于瑞梅刘汉满穆振强
Owner SHANDONG YUANLITAI MEDICAL TECH CO LTD
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