Preparation method of high-purity hyodeoxycholic acid

A high-purity technology for hyodeoxycholic acid, which is applied in the field of preparation of high-purity hyodeoxycholic acid, can solve the problems of cumbersome process, low liquid phase purity, and long production cycle, and achieve simple process operation, friendly solvent environment, and high-quality products. The effect of high purity

Active Publication Date: 2014-05-07
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. Ethyl acetate or acetone recrystallization method. The main disadvantage of this technology is that although it can produce products with a melting point above 195, the liquid phase purity of the product is low, and the liquid phase purity of hyodeoxycholic acid is between 88-95%.
[0006] 2. Methyl esterification acetylate derivation method, although this technology can produce high-purity hyodeoxycholic acid, the purity of hyodeoxycholic acid is more than 98%, but strong carcinogens such as benzene are used in the process, and the process is cumbersome and unsuitable Industrial production
[0007] 3. Chromatographic column method. This technology first methylates the crude product of hyodecholate, and then separates it on a silica gel column. The main disadvantage of this method is that the production cycle is long and the production efficiency is low
[0008] Therefore, in order to improve the purity of hyodeoxycholic acid products and overcome the defects of existing HDCA purification methods such as complicated process, difficult operation, long production cycle, and high cost, it is urgent to develop a method that is easy to process large-scale production, low cost, and short production cycle. technical method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1. Preparation of crude product of hyodeoxycholic acid

[0034] Take 100g of bilirubin leftovers, add 30g of sodium hydroxide or potassium hydroxide, 200ml of water, saponify at 98°C for 20h, cool to room temperature, let it stand, siphon out the supernatant and discard it, add 200ml of water to the paste in the lower layer, and stir Dissolve, add concentrated hydrochloric acid to acidify until the Congo red test paper turns blue, add 800ml ethyl acetate, stir and extract for 30min, let stand to separate layers, and discard the water phase. Add 800ml of water to the ethyl acetate phase and wash until the water phase pH=6, add 20g of anhydrous sodium sulfate to the ethyl acetate phase for dehydration, decolorize with 10g of activated carbon for 30min, filter, concentrate to about 160ml, there is precipitation, cool to 3°C, filter or press , vacuum-dried crude hyodeoxycholic acid 35g.

[0035] 2. Preparation of hyodeoxycholate amine salt

[0036] Add 200ml of absolute e...

Embodiment 2

[0040] 1. Preparation of crude product of hyodeoxycholic acid

[0041] Take 100g of bilirubin leftovers, add 10g of sodium hydroxide or potassium hydroxide, 10g of water, saponify at 95°C for 16h, cool to room temperature, let it stand, siphon out the supernatant and discard it, add 200ml of water to the paste in the lower layer, and stir Dissolve, add 50% sulfuric acid to acidify until the Congo red test paper turns blue, add 600ml ethyl acetate, stir and extract for 30min, let stand to separate layers, and discard the water phase. Add 800ml of water to the ethyl acetate phase and wash until the water phase pH=6, add 10g of anhydrous sodium sulfate to the ethyl acetate phase for dehydration, decolorize with 10g of activated carbon for 30min, filter, concentrate to about 160ml, there is precipitation, cool to 0°C, filter or press , vacuum-dried crude hyodeoxycholic acid 34.8g.

[0042] 2. Preparation of hyodeoxycholate amine salt

[0043] Add 200ml of absolute ethanol to 34....

Embodiment 3

[0047] 1. Preparation of crude product of hyodeoxycholic acid

[0048] Take 1000ml of fresh pig bile, add 50g of sodium hydroxide or potassium hydroxide, 300ml of water, saponify at 100°C for 24 hours, cool to room temperature, let stand, siphon out the supernatant and discard, add 200ml of water to the lower paste, stir to dissolve, Add concentrated hydrochloric acid to acidify until the Congo red test paper turns blue, add 1000ml ethyl acetate, stir and extract for 30min, let stand to separate the layers, and discard the water phase. Add 1000ml of water to the ethyl acetate phase and wash until the pH of the water phase is 7, add 19.5g of anhydrous sodium sulfate to the ethyl acetate phase for dehydration, decolorize with 10g of activated carbon for 30min, filter, concentrate to about 160ml, there is precipitation, cool to 5°C, filter or Squeeze, vacuum-dried crude hyodeoxycholic acid 34.2g.

[0049] 2. Preparation of hyodeoxycholate amine salt

[0050]Add 250 ml of absolu...

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PUM

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Abstract

The invention discloses a preparation method of high-purity hyodeoxycholic acid. The preparation method comprises the steps: weighing raw materials, adding strong alkaline and water, saponifying at the temperature of 95-100 DEG C for 16-24h, cooling to room temperature, standing, siphoning to remove a supernatant liquid, adding water into paste in the lower layer, stirring for dissolving the paste, adding strong acid to acidize until a congo red test paper turns to be blue, adding ethyl acetate, stirring for extracting for 20-50min, standing for layering, removing a water phase, adding water into the ethyl acetate to wash until the pH value of the water phase is equal to 6-7, adding the ethyl acetate into anhydrous sodium sulfate to dehydrate, carrying out activated carbon decoloration, filtering, concentrating until precipitates are separated out, cooling, filtering or squeezing and drying in vacuum; adding an alcohol solvent, stirring for dissolving the above product, slowly adding an alkaline organic solvent, stirring, cooling, separating out a great number of precipitates, filtering and drying; and adding water and sodium hydroxide, stirring for dissolving, dropwise adding hydrochloric acid with a volume concentration of 1:1, stirring, filtering and drying to obtain the hyodeoxycholic acid. The invention aims to provide the preparation method of the hyodeoxycholic acid with simple process, high yield and high purity.

Description

technical field [0001] The invention relates to a preparation method of high-purity hyodeoxycholic acid. Background technique [0002] Hyodesoxycholic acid (Hyodesoxycholic Acid, HDCA) is a biochemical substance widely present in animal bile, with a content of 0.1% to 0.2%. Its chemical name is 3α, 6α-dihydroxy-5β-cholanic acid, and its molecular formula is C 24 h 40 o 4 , with a molecular weight of 392.58, easily soluble in ethanol, slightly soluble in acetone, very slightly soluble in ethyl acetate, chloroform or ether, almost insoluble in water. HDCA has the effects of lowering blood fat, antispasmodic and expectorant, and is clinically used to treat hyperlipidemia, atherosclerosis, tracheitis, viral upper respiratory tract inflammation in children, and dyspepsia caused by liver and gallbladder diseases; , Bacillus diphtheriae, Staphylococcus aureus, etc. have a certain inhibitory effect; as an active ingredient in Qingkailing injection, it has a good effect on the tre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 沈惠宾祝国祥刘骅李晓鹤
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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