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Preparation method of murine deoxycholic acid

A technology of deoxycholic acid and hyodeoxycholic acid, which is applied in the field of preparation of murine deoxycholic acid, and achieves the effects of high conversion rate, less side reactions and wide source of raw materials

Inactive Publication Date: 2021-10-26
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the report of the preparation method of murine deoxycholic acid has not yet appeared, so it is necessary to study a simple, convenient and suitable method for the preparation of murine deoxycholic acid for mass production, so as to provide data support and standard samples for follow-up research

Method used

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  • Preparation method of murine deoxycholic acid
  • Preparation method of murine deoxycholic acid

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Experimental program
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Embodiment 1

[0033] The preparation method of the murine deoxycholic acid of the present embodiment, comprises the steps:

[0034] a. Preparation of 3,6-dicarbonyl-5β-cholanic acid

[0035] Add 10g of hyodeoxycholic acid and 50ml of acetone into a 500ml reaction bottle, lower the temperature to below 0°C, slowly add 46ml of hypochlorous acid with a content of 10%, and continue to react for 30min after the addition is completed. The residual hyodeoxycholic acid detected by HPLC is 0.237 %, add 0.3g sodium bisulfite to terminate the reaction; distill off acetone, add 200ml water and stir for 30min to crystallize completely, filter, wash the filter cake with 2*250ml water, until the washing water is neutral by pH test paper, and 3,6- The wet product of dicarbonyl-5β-cholanic acid is about 12.5 g, and the purity detected by HPLC is 98.352%.

[0036] b. Preparation of 3α-hydroxy, 6-carbonyl-5β-cholanic acid

[0037] Dissolve the 3,6-dicarbonyl-5β-cholanic acid in the previous step in 100ml of...

Embodiment 2

[0041] a. Preparation of 3,6-dicarbonyl-5β-cholanic acid

[0042] Add 10g of hyodeoxycholic acid and 80ml of acetone into a 500ml reaction bottle, cool down to below 0°C, slowly add 13.4ml of Jones reagent (mixed solution of chromium trioxide and sulfuric acid), continue to react for 30min after adding, sample HPLC for detection of hyodeoxychol The acid residue was 0.127%, and 0.3 g of sodium bisulfite was added to terminate the reaction. Distill to remove acetone, add 200ml of water and stir for 30min to crystallize completely, filter, wash the filter cake with 2*250ml of water until the washed water is neutral by pH test paper, and the wet product of 3,6-dicarbonyl-5β-cholanic acid is about 12.7 g, the purity detected by HPLC is 98.257%.

[0043] b. Preparation of 3α-hydroxy, 6-carbonyl-5β-cholanic acid

[0044] Dissolve the 3,6-dicarbonyl-5β-cholanic acid in the previous step in 105ml of 1% sodium hydroxide solution, adjust the pH of the solution to 7.0-7.5, add 5.5g of g...

Embodiment 3

[0048] a. Preparation of 3,6-dicarbonyl-5β-cholanic acid

[0049] Add 10g of hyodeoxycholic acid and 100ml of acetone into a 500ml reaction bottle, lower the temperature to below 0°C, slowly add 40ml of saturated potassium permanganate solution, and continue the reaction for 30min after the addition is complete. The residual hyodeoxycholic acid is detected by sampling HPLC as 0.226%. 0.3 g of sodium bisulfite was added to terminate the reaction. Distill to remove acetone, add 200ml of water and stir for 30min to completely crystallize, filter, wash the filter cake with 2*250ml of water until the washing water is neutral by pH test paper, and the wet product of 3,6-dicarbonyl-5β-cholanic acid is about 13.2 g, the purity detected by HPLC is 98.066%.

[0050] b. Preparation of 3α-hydroxy, 6-carbonyl-5β-cholanic acid

[0051] Dissolve the 3,6-dicarbonyl-5β-cholanic acid in the previous step in 110ml of 1% sodium hydroxide solution, adjust the pH of the solution to 7.0-7.5, add 6g ...

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Abstract

The invention discloses a preparation method of murine deoxycholic acid, which is characterized in that hyodeoxycholic acid (3alpha, 6alpha-dihydroxyl-5beta-cholanic acid) is used as a raw material, and the process comprises the steps of 3, 7-site hydroxyl oxidation, 3-site carbonyl reduction, 7-site carbonyl reduction and purification to obtain high-purity murine deoxycholic acid (3alpha, 6beta-dihydroxyl-5beta-cholanic acid). The murine deoxycholic acid synthesized and prepared through the route is wide in raw material source and sufficient in supply; and the method has the advantages of high yield, high purity and few side reactions, is suitable for large-scale preparation, and can provide data support and standard samples for subsequent related researches.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically refers to a preparation method of murine deoxycholic acid. Background technique [0002] Bile acids are an important component of bile. Bile acids mainly exist in the enterohepatic circulatory system and play a protective role through recirculation. Bile acids are important endogenous molecules related to numerous biological functions, including the absorption and excretion of cholesterol, It plays a role in promoting lipid emulsification and enhancing pancreatic lipolysis in metabolism, directly participates in lipid and glucose metabolism, and has an extremely close relationship with obesity and immune response; and in terms of clinical and disease diagnosis, bile acid plays a role in Played an important role in the study of hepatobiliary and gastrointestinal diseases. [0003] Murodeoxycholic acid is an important secondary bile acid in the metabolic process of rodent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 秦和平张和平祝国祥林志锋凌芬娜
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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