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

Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles

The biotransformations of cholic acid (1a), deoxycholic acid (1b), and hyodeoxycholic acid (1c) to bendigoles and other metabolites with bacteria isolated from the rural slaughterhouse of Cayambe (Pichincha Province, Ecuador) were reported. The more active strains were characterized, and belong to the genera Pseudomonas and Rhodococcus. Various biotransformation products were obtained depending on bacteria and substrates. Cholic acid (1a) afforded the 3-oxo and 3-oxo-4-ene derivatives 2a and 3a (45% and 45%, resp.) with P.?mendocina ECS10, 3,12-dioxo-4-ene derivative 4a (60%) with Rh.?erythropolis ECS25, and 9,10-secosteroid 6 (15%) with Rh.?erythropolis ECS12. Bendigole F (5a) was obtained in 20% with P.?fragi ECS22. Deoxycholic acid (1b) gave 3-oxo derivative 2b with P.?prosekii ECS1 and Rh.?erythropolis ECS25 (20% and 61%, resp.), while 3-oxo-4-ene derivative 3b was obtained with P.?prosekii ECS1 and P.?mendocina ECS10 (22% and 95%, resp.). Moreover, P.?fragi ECS9 afforded bendigole A (8b; 80%). Finally, P.?mendocina ECS10 biotransformed hyodeoxycholic acid (1c) to 3-oxo derivative 2c (50%) and Rh.?erythropolis ECS12 to 6α-hydroxy-3-oxo-23,24-dinor-5β-cholan-22-oic acid (9c, 66%). Bendigole G (5c; 13%) with P.?prosekii ECS1 and bendigole H?(8c) with P.?prosekii ECS1 and Rh.?erythropolis ECS12 (20% and 16%, resp.) were obtained.

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.