Preparation method of 7-dehydrocholesterol

A technology for dehydrocholesterol and cholesterol, applied in the direction of steroids, chemical recovery, organic chemistry, etc., can solve the problem of low yield and achieve the effects of increased yield, high active bromine content, and economical use

Inactive Publication Date: 2012-10-03
HENAN LIWEI BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(3) Synthesis by biosynthesis, such as using 7-ene cholestanol as raw material to synthesize the target product, the yield of the above method is generally not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. A method for preparing 7-dehydrocholesterol, comprising the steps of:

[0021] 1) Esterification reaction

[0022] Cholesterol + Benzoyl Chloride → Cholesterol Benzoate

[0023] Material molar ratio: cholesterol: benzoyl chloride 1:1.5

[0024] The synthesis of cholesteryl benzoate is carried out in two steps, one is the synthesis of benzoyl chloride, and the other is the synthesis of cholesteryl benzoate with benzoyl chloride and cholesterol as raw materials. The specific implementation plan is as follows:

[0025] React freshly steamed thionyl chloride with benzoic acid at room temperature for 1 hour at 50±5°C (the molar ratio of thionyl chloride to benzoic acid is 1.05:1), then raise the temperature to 90°C for 2 hours. Excessive thionyl chloride was distilled off at normal pressure, and then benzoyl chloride was distilled off under reduced pressure as the raw material for the next reaction.

[0026] Dissolve cholesterol in dry benzene, add pyridine [W 胆固醇 (g...

Embodiment 2

[0039] 1. A method for preparing 7-dehydrocholesterol, comprising the steps of:

[0040] 1) Esterification reaction

[0041] Cholesterol + Benzoyl Chloride → Cholesterol Benzoate

[0042] Material molar ratio: cholesterol: benzoyl chloride 1:0.9

[0043] The synthesis of cholesteryl benzoate is carried out in two steps, one is the synthesis of benzoyl chloride, and the other is the synthesis of cholesteryl benzoate with benzoyl chloride and cholesterol as raw materials. The specific implementation plan is as follows:

[0044] React freshly steamed thionyl chloride with benzoic acid at room temperature for 1 hour at 50±5°C (the molar ratio of thionyl chloride to benzoic acid is 1.05:1), then raise the temperature to 90°C for 2 hours. Excessive thionyl chloride was distilled off at normal pressure, and then benzoyl chloride was distilled off under reduced pressure as the raw material for the next reaction.

[0045] Dissolve cholesterol in dry benzene, add pyridine [W 胆固醇 (g...

Embodiment 3

[0057] 1. A method for preparing 7-dehydrocholesterol, comprising the steps of:

[0058] 1) Esterification reaction

[0059] Cholesterol + Benzoyl Chloride → Cholesterol Benzoate

[0060] Material molar ratio: cholesterol: benzoyl chloride 1:1.9

[0061] The synthesis of cholesteryl benzoate is carried out in two steps, one is the synthesis of benzoyl chloride, and the other is the synthesis of cholesteryl benzoate with benzoyl chloride and cholesterol as raw materials. The specific implementation plan is as follows:

[0062] React freshly steamed thionyl chloride with benzoic acid at room temperature for 1 hour at 50±5°C (the molar ratio of thionyl chloride to benzoic acid is 1.05:1), then raise the temperature to 90°C for 2 hours. Excessive thionyl chloride was distilled off at normal pressure, and then benzoyl chloride was distilled off under reduced pressure as the raw material for the next reaction.

[0063] Dissolve cholesterol in dry benzene, add pyridine [W 胆固醇 (g...

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PUM

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Abstract

The invention discloses a preparation method of 7-dehydrocholesterol. The preparation method comprises four steps of esterifying, brominating, de-brominating, saponifying and hydrolyzing. In the brominating reaction process, the brominating agent, namely N-brominated succimide (NBS) with advantages of high location, high active bromine content, good storage stability and economic usage is selected. Due to the brominating agent, the side reaction is less during the preparation; the by-product is few and a plurality of steps of removing brominating by-products are saved; due to the mol concentration proportion of the method, the yield of the target product is notably improved.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for preparing 7-dehydrocholesterol. Background technique [0002] Vitamin D3 is an essential fat-soluble vitamin for the growth, reproduction, maintenance of life and health of humans, livestock and livestock. Its main function is to regulate calcium and phosphorus metabolism, promote intestinal calcium and phosphorus absorption and bone calcification, and maintain blood calcium and Blood phosphorus balance. Vitamin D3 is mainly used in three aspects: pharmaceutical preparations, food additives and feed additives. As a pharmaceutical preparation, it is mainly used clinically to treat rickets, rickets, osteoporosis, hypothyroidism and other diseases; as a food and beverage additive, It can be added to milk, dairy products, biscuits, candies and various beverages to prevent vitamin D deficiency; vitamin D3 can be used as a feed additive for livestock and poultry, which c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCY02P20/582
Inventor 薛家禄马志军
Owner HENAN LIWEI BIOLOGICAL PHARMA
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