88179-71-9

Basic information

• Product Name: 3-oxo-chola-4,6-dien-24-oic acid
• Synonyms: 3-Oxo-4,6-choladienoic acid;3-oxo-chola-4,6-dien-24-oic acid;Chola-4,6-dien-24-oicacid, 3-oxo-
• CAS NO: 88179-71-9
• Molecular Formula: C24H34O3
• Molecular Weight: 370.52
• Mol File: 88179-71-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 541.8°C at 760 mmHg
• Flash Point: 295.6°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 3.55E-13mmHg at 25°C
• Refractive Index: 1.559
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: 3-oxo-chola-4,6-dien-24-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxo-chola-4,6-dien-24-oic acid(88179-71-9)
• EPA Substance Registry System: 3-oxo-chola-4,6-dien-24-oic acid(88179-71-9)

Safety Data

• Hazardous Substances Data: 88179-71-9(Hazardous Substances Data)

Usage

Uses

3-Oxo-4,6-choladien-24-oic Acid is an intermediate in the synthesis of various bile acids.

Definition

ChEBI: A 3-oxo Delta4-steroid that is the 3-oxo derivative of chola-4,6-dien-24-oic acid.

InChI:InChI=1/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/t15-,18+,19-,20+,21+,23+,24-/m1/s1

Upstream product

• 128-13-2 ursodeoxycholic acid 
• 106351-13-7 4β-bromo-7α-formyloxy-3-oxo-5β-cholanic acid 
• 106351-12-6 7α-formyloxy-3-oxo-5α-cholanic acid 
• 944409-56-7 cholan-4,6-dien-3-one-24-al 

Relevant articles and documents

PROCESS FOR PRODUCTION OF STEROIDS

It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.

POTENTIAL BILE ACID METABOLITES. X. SYNTHESES OF STEREOISOMERIC 3,7-DIHYDROXY-5α-CHOLANIC ACIDS

New synthetic routes to allochenodeoxycholic (3α,7α-dihydroxy-5α-cholanic) and alloursodeoxycholic (3α,7β-dihydroxy-5α-cholanic) acids, and their stereoisomers are described.Treatments of allo 7α-hydroxy-3β-tosyloxy ester with N,N-dimethylformamide and of allo 7α-mesyloxy-3β-tosyloxy and 3β-cathyloxy-7α-mesyloxy esters with potassium superoxide-crown ether afforded the desired 3α,7α-, 3α,7β-, and 3β,7β-dihydroxy stereoisomers, respectively, in high yield.Highperformance liquid chromatography was of key importance in characterizing the compounds and determining their purity.Keywords--bile acid; allo bile acid; 3,7-dihydroxy-5α-cholanic acid; allochenodeoxycholic acid; alloursodeoxycholic acid; N,N-dimethylformamide reaction; potassium superoxide-18-crown-6 ether reaction; HPLC