3-Oxocholic acid

Base Information

• Chemical Name: 3-Oxocholic acid
• CAS No.: 2304-89-4
• Molecular Formula: C24H38 O5
• Molecular Weight: 406.563
• UNII: NFU5ZM6X6V
• DSSTox Substance ID: DTXSID801316583
• Nikkaji Number: J324.811I
• Wikidata: Q27160056
• Metabolomics Workbench ID: 36431
• Mol file: 2304-89-4.mol

Synonyms:3-oxocholic acid;7,12-dihydroxy-3-oxocholanic acid;7alpha,12alpha-dihydroxy-3-oxo-cholanoic acid

Chemical Property of 3-Oxocholic acid

Chemical Property:

• Vapor Pressure: 5.08E-16mmHg at 25°C
• Melting Point: 185 °C
• Boiling Point: 583°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 320.4°C
• PSA: 94.83000
• Density: 1.18g/cm³
• LogP: 3.65690
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly)
• XLogP3: 3.2
• 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:

98%min ^*data from raw suppliers

3-Oxo-7α,12α-hydroxy-5β-cholanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(=O)C4)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCC(=O)C4)C)O)O)C
• Uses: 3-Oxo-7α,12α-hydroxy-5β-cholanoic Acid is a keto bile acid derivative.

Technology Process of 3-Oxocholic acid

There total 5 articles about 3-Oxocholic 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: 45.0%

sodium cholate (361-09-1) → 3-oxo-7α,12α-dihydroxy-4-cholen-24-oic acid (13587-11-6) + 7α,12α-dihydroxy-3-oxocholanoic acid (2304-89-4)

Guidance literature:

With Pseudomonas mendocina ECS₁₀; In water; at 28 ℃; for 72h; Microbiological reaction;

DOI:10.1002/cbdv.201500300

Reference yield: 23.0%

dehydrocholic acid (81-23-2) → cholic acid (81-25-4) + 7α,12α-dihydroxy-3-oxocholanoic acid (2304-89-4) + 7α,12β-dihydroxy-3-keto-5β-cholan-24-oic acid (153222-72-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 10h; Further Variations:; Reagents; Solvents; Product distribution;

DOI:10.1016/j.steroids.2006.01.004

Reference yield:

dehydrocholic acid (81-23-2) → 7α,12α-dihydroxy-3-oxocholanoic acid (2304-89-4) + 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid (2458-08-4) + 7-ketodeoxycholic acid (911-40-0)

Guidance literature:

With sodium tetrahydroborate; sodium hydrogencarbonate; at 0 ℃; for 24h;

DOI:10.1246/cl.1996.335

upstream raw materials:

dehydrocholic acid

sodium cholate

Downstream raw materials:

3-oxo-7α,12α-dihydroxy-4-cholen-24-oic acid

methyl 3-oxo-7α,12α-dihydroxy-5α-cholan-24-oate

3-oxo cholic acid methyl ester

3-deoxycholic acid

Refernces

• 1、 Miro,Marin,Miranda. "Radical-mediated dehydrogenation of bile acids by means of hydrogen atom transfer to triplet carbonyls". . p. 2679 - 2683. Retrieved 2016/03/05.
• 2、 Cravotto, Giancarlo,Binello, Arianna,Boffa, Luisa,Rosati, Ornelio,Boccalini, Marco,Chimichi, Stefano. "Regio- and stereoselective reductions of dehydrocholic acid". . p. 469 - 475. Retrieved 2007/10/03.