10538-65-5

Usage

Uses

Used in Pharmaceutical Industry:
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester is used as a hepatoprotective agent for its potential to protect the liver from damage and inflammation. Its anti-inflammatory properties contribute to its therapeutic effects in liver disease treatment.
Used in Cholelitholytic Applications:
In the medical field, (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester is utilized as a choleretic agent to increase bile secretion and as a cholelitholytic agent to aid in the dissolution of gallstones, thereby improving bile flow and reducing the formation of new stones.
Used in Liver Disease Treatment:
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester is employed as a therapeutic agent for the treatment of various liver diseases, leveraging its hepatoprotective properties to support liver health and function.

Upstream product

• 67-56-1 methanol 
• 81-25-4 cholic acid 
• 21059-36-9 3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester 
• 1448-36-8 methyl cholate 
• 64-19-7 acetic acid 
• 911-40-0 7-ketodeoxycholic acid 

Downstream Products

• 21066-20-6 methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) 
• 474-25-9 chenodeoxycholic acid 
• 83-44-3 Deoxycholic acid 
• 128-13-2 ursodeoxycholic acid 
• 10452-65-0 methyl 3α-acetoxy-7-oxo-5β-cholan-24-oate 
• 10538-59-7 7-ketolithocholic methyl ester 
• 336099-76-4 methyl 3α-[(1,1-dimethylethyl)dimethylsilyloxy]-7-oxocholan-24-oate 
• 4651-67-6 7-Ketolithocholic acid 
• 133181-50-7 methyl 3α,12α-diformyloxy-7-oxo-5β-cholan-24-oate 
• 1351984-94-5 3α,12α-di(tert-butyldimethylsilyloxy)-7,24-diallyloxy-7,8-seco-5β-cholan-8α-ol 
• 1351984-93-4 C₃₆H₇₂O₅Si₂ 
• 133181-57-4 methyl 12α-acetoxy-3α,6α,7α-trihydroxy-5β-cholanoate 
• 133181-56-3 methyl 12α-acetoxy-3α,6α-dihydroxy-7-oxo-5β-cholanoate 
• 80875-93-0 3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid 

Relevant academic research and scientific papers

Exploitation of a laccase/meldola's blue system for NAD+ regeneration in preparative scale hydroxysteroid dehydrogenase-catalyzed oxidations

An enzymatic regeneration system consisting of laccase and the 2H +/2e- redox mediator Meldola's blue (MB) was developed for the efficient oxidation of reduced nicotinamide adenine dinucleotide (NADH) cofactor and employed in the gram-scale oxidation of cholic acid (1) to its 7-keto derivative (1a) by 7a-hydroxysteroid dehydrogenase (7a- HSDH) in an aqueous, buffered reaction system. The regenerating enzyme, laccase, reduces molecular oxygen as terminal 4H+/4e- acceptor to water and concomitantly reoxidizes NADH via MB at high turnover rates. The regeneration system was successfully applied to quantitatively convert 1 (50 mM, 20.4 g) into 1a with a space-time yield of 5.8 mmolL-1h-1. High total turnover numbers were achieved for 7a-HSDH (4.2×105) and laccase (1.1× 10.6). Alternatively, the regeneration system was employed on the conversion of the methyl ester derivative of cholic acid (2, 200 mM, 5.9 g) dissolved in isopropyl acetate as organic solvent in a biphasic system. Due to the high concentration of 2 and the excellent performance of the enzymatic cascade reaction even under the harsh process conditions, space-time yields of up to 20 mmolL-1h-1(8.5 gL-1h -1) of the produced 7-keto derivative 2a were obtained. The irreversibility and high driving force of the regenerating reaction allowed quantitative conversions and easy product recovery.

Method for synthesizing deoxycholic acid

The invention provides a method for synthesizing deoxycholic acid. The method comprises the steps of esterifying cholic acid to obtain a compound I, oxidizing to obtain a compound II, performing protection to obtain a compound III, brominating to obtain a compound IV, reducing to obtain a compound V, eliminating to obtain a compound VI, reducing and hydrogenating to obtain a compound VII, and performing ester hydrolysis to obtain deoxycholic acid. The reaction formula is shown in the description, wherein R1 in the formula III, the formula VI, the formula V, the formula VI and the formula VII is selected from benzoyl or p-toluenesulfonyl; and R2 is selected from methyl, ethyl or tertiary butyl. The synthesis method overcomes the defects of long reaction steps, expensive used reagents, difficulty in purification, low yield and the like in the prior art, and provides a novel method which is rapid in reaction, easy in purification, high in yield and suitable for commercial mass production.

Synthesis method of 3[alpha],6[alpha](beta),12[alpha]-trihydroxyl-5[beta]-cholic acid

The invention discloses a preparation method of 3[alpha],6[alpha],12[alpha]-trihydroxyl-5[beta]-cholic acid and 3[alpha],6[beta],12[alpha]-trihydroxyl-5[beta]-cholic acid. 3[alpha],7[alpha],12[alpha]-trihydroxyl-5[beta]-cholic acid is taken as a raw material, and 3[alpha],6[alpha],12[alpha]-trihydroxyl-5[beta]-cholic acid and 3[alpha],6[beta],12[alpha]-trihydroxyl-5[beta]-cholic acid are obtainedthrough ten steps such as Mukaiyama aldol condensation reaction, oxidative cracking, reduction removal and the like . The synthesis method has the characteristics of green and high efficiency.

A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

PROCESS FOR THE PREPARATION OF DEOXYCHOLIC ACID

The present invention provides a process for preparation of deoxycholic acid or salt thereof; the process comprises the steps of reacting the compound of formula II to obtain a compound of formula III; the compound of formula III is converted to a compound of formula IV and the compound of formula IV is converted to deoxycholic acid. The present invention also provides a process for the purification of deoxycholic acid or salt thereof.

METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF

The present application relates to a method of preparing compounds of Formula (A) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof.

Synthesis method for obeticholic acid intermediate 7-ketolithocholic acid

The invention discloses a chemical synthesis method for an obeticholic acid intermediate 7-ketolithocholic acid (3alpha-hydroxy-7-keto-5beta-cholestane-24-acid), and belongs to the field of organic chemical synthesis. The method adopts cholic acid as a raw material, and through 7alpha-hydroxyl selective oxidation, side chain carboxyl esterification, 3alpha-hydroxyl etherification, 12alpha-hydroxyl methanesulfonic acid esterification, elimination, hydrogenation, hydrolysis and other reactions, the obeticholic acid intermediate 7-ketolithocholic acid is synthesized. The synthesis method for 7-ketolithocholic acid adopts cheap cholic acid as the raw material, and has the advantages of novel synthesis method, low cost, high yield, environmental friendliness and convenience in industrialized production.

Synthetic method of 7-keto-lithocholic acid

The invention discloses a chemical synthetic method of an intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, and belongs to the field of organic chemical synthesis. According to the chemical synthetic method of the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, cholic acid is adopted as a raw material, and through reactions of selective oxidization of 7alpha-hydroxyl, esterification of side chain carboxyl groups, esterification of 3alpha-hydroxyl, methanesulfonic acid esterification, elimination, hydrogenation, and hydrolysis of 12alpha-hydroxyl, the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid is synthesized. According to the chemical synthetic method of the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, cheap cholic acid is adopted as the raw material, the synthesis method is novel, low in cost, high in yield and environmentally friendly, which facilitates industrialized production.

[...] synthetic method and intermediate (by machine translation)

The invention discloses a method for synthesizing [...], the cholic acid as the raw material, after 7 α - hydroxy selective oxidation, side chain carboxyl ester, 3 α - hydroxy ester, 12 α - hydroxy methanesulfonic acid esterification, eliminate, selective hydrolysis of 3 bit ester group, with the three-a chlorosilane reaction to produce the silicon ether, with acetaldehyde to aldol condensation, and the hydrolysis, catalytic hydrogenation reduction olefinic bond, carbonyl reduction reaction such as, to synthesize states the aobeiaobei cholic acid. The method of the invention uses cheap cholic acid as raw materials, synthetic method is novel, low cost, high yield, mild reaction conditions, easy post treatment, environmental friendly, convenient to industrial production. (by machine translation)

Chenodeoxycholic acid synthesis method

The invention discloses a chenodeoxycholic acid synthesis method, wherein cholic acid is used as a raw material, and 7[alpha]-hydroxyl selective oxidation, side-chain carboxyl esterification, 3[alpha]-hydroxyl esterification, 12[alpha]-hydroxymethanesulfonic acid esterification, elimination, hydrolysis, reduction and other reactions are performed to prepare the chenodeoxycholic acid. According to the present invention, the chenodeoxycholic acid synthesis method has advantages of simple step, less side reaction, high yield and easily available raw materials, is suitable for industrial production, can solve the problems of high synthesis cost, low yield and the like in the prior art, and is suitable for industrial mass-production.