7-Ketodeoxycholic acid

Base Information

• Chemical Name: 7-Ketodeoxycholic acid
• CAS No.: 911-40-0
• Molecular Formula: C24H38 O5
• Molecular Weight: 406.563
• UNII: 14DEP88BGS
• DSSTox Substance ID: DTXSID101314217
• Nikkaji Number: J324.812G
• Wikidata: Q27101883
• Metabolomics Workbench ID: 36425
• ChEMBL ID: CHEMBL3392000
• Mol file: 911-40-0.mol

Synonyms:3 alpha,12 alpha-diol-7-one-5 beta-cholanoic acid;3 alpha,7 alpha-dihydroxy-7-keto-5 beta-cholanoic acid;7-ketodeoxycholic acid;7-ketodeoxycholic acid, (3alpha,12alpha)-isomer;7-oxodeoxycholic acid

Chemical Property of 7-Ketodeoxycholic acid

Chemical Property:

• Vapor Pressure: 5.08E-16mmHg at 25°C
• Melting Point: 54-60°C
• Boiling Point: 583°Cat760mmHg
• Flash Point: 320.4°C
• PSA: 94.83000
• Density: 1.18g/cm³
• LogP: 3.65690
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• 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:

97% ^*data from raw suppliers

7-Keto-3α,12-α-dihydroxycholanicAcid ^*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(=O)CC4C3(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[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: 7-Keto-3α,12-α-dihydroxycholanic Acid (cas# 911-40-0) is a compound useful in organic synthesis.

Technology Process of 7-Ketodeoxycholic acid

There total 27 articles about 7-Ketodeoxycholic 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: 100.0%

Sodium; (R)-4-((5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoate → 7-ketodeoxycholic acid (911-40-0)

Guidance literature:

With phosphate buffer; 3α-HSDH from Pseudomonas paucimobilis; NAD; iso-butanol; In water; at 22 ℃; for 48h;

DOI:10.1016/S0040-4020(98)01111-9

Reference yield: 95.0%

cholic acid (81-25-4) → 7-ketodeoxycholic acid (911-40-0)

Guidance literature:

With N-Bromosuccinimide; sodium hydrogencarbonate; at 20 ℃; for 19h; Product distribution / selectivity; Reflux;

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

upstream raw materials:

cholic acid

methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate)

acetic acid

acetone

Downstream raw materials:

methyl 3α,12α-dihydroxy-7-oxo-5β-cholate

3α.12α-diformyloxy-7-oxo-5β-cholanoic acid-(24)

3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid ethyl ester

(R)-4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-Dihydroxy-10,13-dimethyl-7-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 4-nitro-phenyl ester