5143-55-5

Usage

Uses

Used in Biochemical Research:
12-KETOLITHOCHOLIC ACID ACETATE, METHYL ESTER is used as a research tool for investigating the effects of bile acids on biological processes. It aids in understanding the intricate mechanisms by which bile acids influence metabolic pathways and contribute to overall health.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 12-KETOLITHOCHOLIC ACID ACETATE, METHYL ESTER is utilized as a potential component in the development of new drugs. Its application is particularly relevant for the treatment of liver and gastrointestinal diseases, where bile acid metabolism plays a significant role in disease progression and management.
Used in Understanding Bile Acid Mechanisms:
12-KETOLITHOCHOLIC ACID ACETATE, METHYL ESTER is employed to explore the mechanisms of action of bile acids within the body. This research is vital for gaining insights into their physiological roles and how they may contribute to pathological conditions, potentially leading to the discovery of novel therapeutic targets and treatment strategies.

Upstream product

• 5130-29-0 12-oxolithocholic acid 
• 88128-14-7 3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester 
• 117863-38-4 3α-acetoxy-11β-bromo-12α-hydroxy-5β-cholan-24-oic acid methyl ester 
• 83-44-3 Deoxycholic acid 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 24637-47-6 methyl 3α-acetoxy-12-hydroxy-9(11)-cholenate 
• 30365-63-0 methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate 
• 571-49-3 3α-hydroxy-5β-androst-9(11)-en-17-one 
• 1093397-63-7 (5β)-androst-9(11)-ene-3,17-dione 
• 1093397-61-5 9α-hydroxy-5β-androstan-3,17-dione 
• 560-62-3 9-alpha-hydroxyandrost-4-ene-3,17-dione 
• 1311972-67-4 C₃₁H₅₀O₆ 

Downstream Products

• 27240-83-1 methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate 
• 5130-29-0 12-oxolithocholic acid 
• 96475-70-6 C₃₄H₅₀N₂O₆S 
• 403607-25-0 3α-hydroxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-oic acid 
• 403607-26-1 3α-hydroxy-12α-N-(3,5-dichlorobenzoyl)amino-5β-cholan-24-oic acid 
• 403607-27-2 methyl 3α-acetyloxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-oate 
• 403607-28-3 methyl 3α-acetyloxy-12α-N-(3,5-dichlorobenzoyl)amino-5β-cholan-24-oate 
• 403607-23-8 N-allyl-N'-methyl-3α-hydroxy-12α-(3,5-dimethylbenzoyl)amino-5β-cholan-24-amide 
• 403607-24-9 N-allyl-N'-methyl-3α-hydroxy-12α-(3,5-dichlorobenzoyl)amino-5β-cholan-24-amide 
• 403607-19-2 N-allyl-N'-methyl-3α-(3,5-dimethylphenyl)carbamoyloxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-amide 
• 403607-21-6 N-allyl-N'-methyl-3α-(3,5-dimethylphenyl)carbamoyloxy-12α-N-(3,5-dichlorobenzoyl)amino-5β-cholan-24-amide 
• 403607-22-7 N-allyl-N'-methyl-3α-(3,5-dichlorophenyl)carbamoyloxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-amide 
• 403607-20-5 N-allyl-N'-methyl-3α-(3,5-dichlorophenyl)carbamoyloxy-12α-(3,5-dichlorobenzoyl)amino-5β-cholan-24-amide 
• 3253-69-8 methyl 3α-acetoxy-5β-cholan-24-oate 

Relevant academic research and scientific papers

PROCESS AND INTERMEDIATES FOR THE 6,7-ALPHA-EPOXIDATION OF STEROID 4,6-DIENES

The invention relates to a process for preparing a compound of general formula (la): wherein R2, Y, R4and R5are as defined herein, wherein the epoxidation is conducted using an oxidant and methyltrioxorhenium as a catalyst (MeReO3). The invention also relates to certain compounds per se.The compounds are intermediates in the synthesis of synthetic bile acids.

6-ALKYL-7-HYDROXY-4-EN-3-ONE STEROIDS AS INTERMEDIATES FOR THE PRODUCTION OF STEROIDAL FXR MODULATORS

The invention relates to compounds of formula (I), wherein R1, R2, Y, R4 and R5 are as defined herein. The compounds are intermediates in the synthesis of synthetic bile acids.

Chemical synthesis of uncommon natural bile acids: The 9α-hydroxy derivatives of chenodeoxycholic and lithocholic acids

The chemical synthesis of the 9α-hydroxy derivatives of chenodeoxycholic and lithocholic acids is reported. For initiating the synthesis of the 9α-hydroxy derivative of chenodeoxycholic acid, cholic acid was used; for the synthesis of the 9α-hydroxy derivative of lithocholic acid, deoxycholic acid was used. The principal reactions involved were (1) decarbonylation of conjugated 12-oxo-Δ9(11)-derivatives using in situ generated monochloroalane (AlH2Cl) prepared from LiAlH4 and AlCl3, (2) epoxidation of the deoxygenated Δ9(11)-enes using m-chloroperbenzoic acid catalyzed by 4,4'-thiobis-(6-tert-butyl-3-methylphenol), (3) subsequent Markovnikov 9a-hydroxylation of the Δ9(11)-enes with AlH2Cl, and (4) selective oxidation of the primary hydroxyl group at C-24 in the resulting 3α,9α,24-triol and 3α,7α,9α,24-tetrol to the corresponding C-24 carboxylic acids using sodium chlorite (NaClO2) in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and sodium hypochlorite (NaOCl). The 1H- and 13C-NMR spectra are reported. The 3α,7α,9α-trihydroxy-5β-cholan-24-oic acid has been reported to be present in the bile of the Asian bear, and its 7-deoxy derivative is likely to be a bacterial metabolite. These bile acids are now available as authentic reference standards, permitting their identification in vertebrate bile acids.

Synthesis and biological activity of novel deoxycholic acid derivatives

We report the synthesis and biological activity of new semi-synthetic derivatives of naturally occurring deoxycholic acid (DCA) bearing 2-cyano-3-oxo-1-ene, 3-oxo-1(2)-ene or 3-oxo-4(5)-ene moieties in ring A and 12-oxo or 12-oxo-9(11)-ene moieties in ring C. Bioassays using murine macrophage-like cells and tumour cells show that the presence of the 9(11)-double bond associated with the increased polarity of ring A or with isoxazole ring joined to ring A, improves the ability of the compounds to inhibit cancer cell growth.

synthetic bile acid preparation

no abstract published

METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID

Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxy-steroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.

METHODS FOR THE SYNTHESIS AND PURIFICATION OF DEOXYCHOLIC ACID

Synthesis and purification of deoxycholic acid and its salts are provided.

METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID

Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxysteroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.

Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: Evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed us to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents.