3-Hydroxy-7,12-diketocholanoic acid

Base Information

• Chemical Name: 3-Hydroxy-7,12-diketocholanoic acid
• CAS No.: 517-33-9
• Molecular Formula: C24H36 O5
• Molecular Weight: 404.547
• DSSTox Substance ID: DTXSID60965969
• Nikkaji Number: J324.813E
• Wikidata: Q63409587
• Metabolomics Workbench ID: 36433
• Mol file: 517-33-9.mol

Synonyms:3 alpha-hydroxy-7,12-diketo-5 beta-cholanoic acid;3-hydroxy-7,12-diketocholanoic acid;3-hydroxy-7,12-diketocholanoic acid, (3beta,5beta)-isomer

Chemical Property of 3-Hydroxy-7,12-diketocholanoic acid

Chemical Property:

• Vapor Pressure: 5.58E-16mmHg at 25°C
• Melting Point: 190-192 °C(Solv: acetone (67-64-1))
• Boiling Point: 582.2°Cat760mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 319.9°C
• PSA: 91.67000
• Density: 1.176g/cm³
• LogP: 3.86510
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 404.25627424
• Heavy Atom Count: 29
• Complexity: 716

Purity/Quality:

98%min ^*data from raw suppliers

3-Hydroxy-7,12-diketocholanoicAcid ^*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(=O)CC3C2C(=O)CC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(C(=O)C[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Uses: 3-Hydroxy-7,12-diketocholanoic Acid is a bile acid salt as biosurfactants.

Technology Process of 3-Hydroxy-7,12-diketocholanoic acid

There total 6 articles about 3-Hydroxy-7,12-diketocholanoic 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: 91.0%

7-ketodeoxycholic acid (911-40-0) → 7,12-dioxolitocholic acid (517-33-9)

Guidance literature:

With Oxalacetic acid; L-malate dehydrogenase from pig heart; nicotinamide adenine dinucleotide-dependent HSDH from Eggerthella lenta; NAD; In methanol; aq. phosphate buffer; at 25 ℃; for 4h; pH=8; Reagent/catalyst; Catalytic behavior; Kinetics; Enzymatic reaction;

DOI:10.1002/adsc.201900144

Reference yield: 90.0%

cholic acid (81-25-4) → 7-ketodeoxycholic acid (911-40-0) + 7,12-dioxolitocholic acid (517-33-9)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tert-butyl alcohol; for 1h; regioselective reaction; Reflux;

DOI:10.1016/j.steroids.2011.07.009

Reference yield: 80.0%

cholic acid (81-25-4) + trimethylpyruvic acid (815-17-8) → L-tert-Leucine (20859-02-3) + 7,12-dioxolitocholic acid (517-33-9)

Guidance literature:

With ammonium hydroxide; leucine dehydrogenase from Exiguobacterium sibiricum; 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid; NAD; 12α-hydroxysteroid dehydrogenase from Rhodococcus ruber; ammonium chloride; In aq. buffer; at 30 ℃; for 24h; pH=9.5; Reagent/catalyst; Time; Catalytic behavior; Green chemistry; Enzymatic reaction;

DOI:10.1039/d1gc01120k

upstream raw materials:

sodium cholate

cholic acid

7-ketodeoxycholic acid

trimethylpyruvic acid

Downstream raw materials:

methyl 3α-hydroxy-7,12-dioxo-5β-cholan-24-oate

Lithocholic acid

Refernces

• 1、 Tonin, Fabio,Alvarenga, Natália,Ye, Jia Zheng,Arends, Isabel W. C. E.,Hanefeld, Ulf. "Clean Enzymatic Oxidation of 12α-Hydroxysteroids to 12-Oxo-Derivatives Catalyzed by Hydroxysteroid Dehydrogenase". supporting information. p. 2448 - 2455. Retrieved 2019/05/22.
• 2、 Dangate, Prasad S.,Salunke, Chetan L.,Akamanchi, Krishnacharya G.. "Regioselective oxidation of cholic acid and its 7β epimer by using o-iodoxybenzoic acid". experimental part. p. 1397 - 1399. Retrieved 2011/11/06.