Method for preparing high-purity hyodeoxycholic acid by pig bile

A technology of hyodeoxycholic acid and pig bile, which is applied in the direction of pharmaceutical formulas, medical preparations containing active ingredients, steroids, etc., can solve the problems of low product purity, high consumption of ethyl acetate and acetone, etc. Achieve the effect of overcoming the low purity of the product, improving the purity of the final product, and reducing the content of impurities

Inactive Publication Date: 2007-09-19
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to overcome defects such as low product purity and high consumption of ethyl acetate and acetone when the existing method is used to produce HDCA, the present invention provides a method that uses pig bile or leftovers (paste) for extracting bilirubin as raw materials. Method for producing high-purity HDCA

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Get the leftovers (paste) 125g that pig bile extracts bilirubin, saponify the leftovers with sodium hydroxide, the weight ratio of feeding intake is: leftovers: water: sodium hydroxide=1: 7: 1.2, by weight ratio For raw materials, first pour 875ml of water into a 2L three-necked flask, then put 150g of sodium hydroxide into the water and stir, and put in the leftovers after it is completely dissolved. Before the temperature rises to 80°C, add a defoamer to prevent excessive air bubbles. Then carefully raise the temperature to 110°C, and reflux for 25h.

[0030] After the saponification reaction is completed, when the reaction solution is cooled to 50°C, the pH of the reaction solution is adjusted to 8 with concentrated sulfuric acid while stirring, and the temperature is maintained at 55-60°C. Then add 5g NaHSO 3 , stirred for 15min. Add 400ml of ethyl acetate, further acidify to pH 5.0 with dilute sulfuric acid while stirring, keep the temperature at 55°C, stir for 3...

Embodiment 2

[0033] Dissolve 30 g of HDCA obtained in Example 1 in 300 ml of methanol, add 4.0 ml of concentrated sulfuric acid for esterification, and stir at room temperature for 24 h. with NaHCO 3 Neutralized to pH 7, the mixture was filtered and concentrated under reduced pressure to obtain an oil.

[0034] The oily substance was dissolved in 350ml of hot benzene, and when the filtrate was concentrated under reduced pressure to about 1 / 2 of the original volume, it was placed in the refrigerator overnight, and a viscous substance was precipitated. Filter and wash the filter cake a little with benzene (methyl hyodeoxycholate-benzene adduct).

[0035] Add 5.5g NaOH and 100ml water to the hyodeoxycholic acid methyl ester-benzene adduct, and steam distill it until the benzene is completely evaporated. After adding 145ml 1N HCl, a precipitate precipitates, wash with water until neutral, and vacuum dry. 27.07g of HDCA with a melting point of 197-198.2° C. was obtained, the yield of this ste...

Embodiment 3

[0037] The crude HDCA obtained in Example 1 was recrystallized with acetone. Take 20g of HDCA crude product, add 500ml of acetone and 5% activated carbon of the solution volume, mix and dissolve, and reflux for 0.5h. Filtrate while hot, wash the residue with acetone, combine the filtrate and washings, concentrate under reduced pressure to 200ml, refrigerate at 0-5°C for 15h, and precipitate crystals. The crystals were separated and dried in vacuum to obtain 13.6 g of white HDCA with a melting point above 196.7° C., with a yield of 68%. The purity was >98% by HPLC detection.

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Abstract

The invention relates to a method for extracting the hyodeoxycholic acid from the leftovers of pig bile or extracted bilirubin, including saponify the leftovers with alkali, adjusting pH value, acetic ester extraction, decoloring with active carbon; concentrating the mother liquid to a proper volume, precipitating deposit, separating the deposit and drying to get coarse hyodeoxycholic acid; esterifying the coarse product, then doing an addition reaction with benzene, separating the methylhyodeoxycholanate-benzene addition compound; decomposing the addition compound with alkali, adjust pH value, getting the purified deoxycholic acid. The obtained mother liquid can be further extracted to get precious chenodeoxycholic acid. The craft has a lot of material, a low pollution, safety and no poison, a low cost, a high product purity and is suitable for industry production in a large scale.

Description

technical field [0001] The invention relates to the field of biochemical pharmacy, in particular to a method for preparing high-purity hyodeoxycholic acid from pig bile (or leftovers from extracting bilirubin). Background technique [0002] Pig bile contains 8.5-12% of bile acids, mainly including four kinds of bile acids, among which hyodeoxycholic acid (HDCA) accounts for 40% of the total bile acids, 3α-hydroxy-6-oxo-5α-cholanic acid accounts for 20% %, chenodeoxycholic acid (CDCA) and hyocholic acid (HCA) account for about 9%, and HDCA and hyocholic acid are characteristic components of pig bile. [0003] HDCA is a blood lipid-lowering drug, which can inhibit the formation of cholic acid and dissolve fat, reduce blood cholesterol and triglycerides, and is suitable for I a or I b Type hyperlipidemia, atherosclerosis. It has a certain antibacterial effect on pertussis bacillus, diphtheria bacillus, and staphylococcus aureus. It can be used as an anti-inflammatory drug t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00A61K35/413A61P1/16
Inventor 徐斌董英王保志丁卫平
Owner JIANGSU UNIV
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