4185-01-7

Basic information

• Product Name: 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID
• Synonyms: 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID;3-Oxo-12α-hydroxy-5β-cholanoic Acid;12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid
• CAS NO: 4185-01-7
• Molecular Formula: C₂₄H₃₈O₄
• Molecular Weight: 390.5561
• Product Categories: Steroids
• Mol File: 4185-01-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 545.9°Cat760mmHg
• Flash Point: 298°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 3.42E-14mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID(4185-01-7)
• EPA Substance Registry System: 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID(4185-01-7)

Safety Data

• Hazardous Substances Data: 4185-01-7(Hazardous Substances Data)

Usage

Description

12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID, also known as 3-Oxo-12a-hydroxy-5β-cholanoic Acid, is a keto bile acid derivative. It is a 3-oxo steroid that is 7-deoxycholic acid in which the hydroxy group at position 3 has undergone formal oxidation to the corresponding ketone.

Uses

Used in Pharmaceutical Industry:
12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID is used as a pharmaceutical compound for its potential therapeutic applications. As a keto bile acid derivative, it may have various roles in the treatment of certain medical conditions related to bile acid metabolism and liver function.
Used in Research and Development:
In the field of research and development, 12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID serves as a valuable compound for studying the structure, function, and potential applications of bile acids and their derivatives. This can lead to the discovery of new drugs and therapies for various health issues.
Used in Chemical Synthesis:
12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID can be used as a starting material or intermediate in the synthesis of other steroidal compounds and related molecules. This makes it an important component in the chemical industry for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-15,17-21,26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,17+,18-,19+,20+,21+,23+,24-/m1/s1

Upstream product

• 3245-38-3 methyl deoxycholate 
• 108-94-1 cyclohexanone 
• 7753-75-5 (R)-methyl 4-((5R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 83-44-3 Deoxycholic acid 
• 302-95-4 sodium cholate 

Downstream Products

• 10538-58-6 methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate 
• 1173-30-4 12-keto-5β-cholan-24-oic acid methyl ester 
• 19684-72-1 12α-hydroxychol-4-en-3-one-24-coic acid methyl ester 

Relevant articles and documents

Deoxycholic acid transformations catalyzed by selected filamentous fungi

More than 100 filamentous fungi strains, mostly ascomycetes and zygomycetes from different phyla, were screened for the ability to convert deoxycholic acid (DCA) to valuable bile acid derivatives. Along with 11 molds which fully degraded DCA, several strains were revealed capable of producing cholic acid, ursocholic acid, 12-keto-lithocholic acid (12-keto-LCA), 3-keto-DCA, 15β-hydroxy-DCA and 15β-hydroxy-12-oxo-LCA as major products from DCA. The last metabolite was found to be a new compound. The ability to catalyze the introduction of a hydroxyl group at the 7(α/β)-positions of the DCA molecule was shown for 32 strains with the highest 7β-hydroxylase activity level for Fusarium merismoides VKM F-2310. Curvularia lunata VKM F-644 exhibited 12α-hydroxysteroid dehydrogenase activity and formed 12-keto-LCA from DCA. Acremonium rutilum VKM F-2853 and Neurospora crassa VKM F-875 produced 15β-hydroxy-DCA and 15β-hydroxy-12-oxo-LCA, respectively, as major products from DCA, as confirmed by MS and NMR analyses. For most of the positive strains, the described DCA-transforming activity was unreported to date. The presented results expand the knowledge on bile acid metabolism by filamentous fungi, and might be suitable for preparative-scale exploitation aimed at the production of marketed bile acids.

STUDIES DIRECTED TOWARD SYNTHESIS OF QUASSINOIDS VII .- CONVERSION OF CHENODEOXYCHOLIC ACID TO A δ-LACTONE QUASSINOID ANALOG AND GENERATION OF A-RING DIOSPHENOL ACETATE DERIVATIVES OF DEOXYCHOLIC ACID

Chenodeoxycholic acid was converted to a new 5,14-epi-28,30-dinorquassinoid analog.Two isomeric A-ring diosphenol acetate derivatives of deoxycholic acid were synthesized.A 3-oxo-5β-steroid was transformed to a 4-acetoxy-3-oxo-Δ4-steroid by treatment with base and oxygen or to a 2-acetoxy-3-oxo-Δ2-steroid by reaction with cupric chloride in refluxing acetic acid followed by acetylation.Ketene extrusion is a characteristic mass spectral fragmentation of these diosphenol acetates.