3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid
• CAS No.: 15173-30-5
• Molecular Formula: C24H38 O5
• Molecular Weight: 406.563
• NSC Number: 66587
• Wikidata: Q76085431
• Metabolomics Workbench ID: 36429
• Mol file: 15173-30-5.mol

Synonyms:3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid;15173-30-5;NSC66587;(4R)-4-[(3R,5R,8S,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid;CHEBI:186602;LMST04010188;NSC-66587

Chemical Property of 3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid

Chemical Property:

• Vapor Pressure: 5.08E-16mmHg at 25°C
• Boiling Point: 583°Cat760mmHg
• Flash Point: 320.4°C
• Density: 1.18g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 406.27192431
• Heavy Atom Count: 29
• Complexity: 676

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(C(=O)C3C2CCC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@@H](C(=O)[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• General Description: (3α,5β,12β)-3,12-Dihydroxy-11-oxocholan-24-oic acid is a bile acid derivative characterized by hydroxyl groups at the 3α and 12β positions, a keto group at C-11, and a carboxylic acid at C-24. Its structure suggests potential roles in steroid metabolism or as an intermediate in bile acid biosynthesis. (3alpha,5beta,12beta)-3,12-dihydroxy-11-oxocholan-24-oic acid has been cataloged under identifiers such as 5β-Cholanic acid, 3α,12β-dihydroxy-11-oxo- (7CI) and NSC 66587, indicating its relevance in chemical and biomedical research. Further studies would be needed to elucidate its specific biological functions or applications.

Technology Process of 3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid

There total 13 articles about 3alpha,12beta-Dihydroxy-11-oxo-5beta-cholan-24-oic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

12-oxolithocholic acid (5130-29-0,83830-81-3) + acetic anhydride (108-24-7) → 3α,12β-dihydroxy-11-oxo-5β-cholan-24-oic acid (15173-30-5)

Guidance literature:

With acetic acid; Erwaermen des Reaktionsgemisches mit Brom in Essigsaeure und Erwaermen des Reaktionsprodukts mit methanol. Kalilauge;

DOI:10.1021/ja01273a017 DOI:10.1021/ja01858a059

Reference yield:

Deoxycholic acid (83-44-3) → 3α,12β-dihydroxy-11-oxo-5β-cholan-24-oic acid (15173-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / anschliessendes Behandeln mit Chrom(VI)-oxid und wss. Essigsaeure und Erhitzen des Reaktionsprodukt mit wss. Kalilauge

2: acetic acid / Erwaermen des Reaktionsgemisches mit Brom in Essigsaeure und Erwaermen des Reaktionsprodukts mit methanol. Kalilauge

With acetic acid;

DOI:10.1021/ja01273a017

Reference yield:

3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester (88128-14-7) → 3α,12β-dihydroxy-11-oxo-5β-cholan-24-oic acid (15173-30-5)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

1-methyl-4-nitrosobenzene

3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester

3α-acetoxy-11α-bromo-12-oxo-5β-cholan-24-oic acid methyl ester

12-oxolithocholic acid

Downstream raw materials:

lithocholenic acid

Lithocholic acid