3-Oxochola-4,6-dien-24-oic Acid

Base Information

• Chemical Name: 3-Oxochola-4,6-dien-24-oic Acid
• CAS No.: 88179-71-9
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532
• UNII: C7WV6M12MR
• DSSTox Substance ID: DTXSID70415288
• Nikkaji Number: J906.649G
• Wikidata: Q27160058
• Metabolomics Workbench ID: 36475
• Mol file: 88179-71-9.mol

Synonyms:3-Oxochola-4,6-dien-24-oic Acid;88179-71-9;3-Oxo-4,6-choladien-24-oic acid;3-Oxo-4,6-choladienoic acid;Chola-4,6-dien-24-oicacid, 3-oxo-;C7WV6M12MR;(4R)-4-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid;Chola-4,6-dien-24-oic acid, 3-oxo-;(4S)-4-((8R,9R,10S,13S,14S,17R)-10,13-Dimethyl-3-oxidanylidene-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthren-17-yl)pentanoic acid;LMST04010235;3-oxo-chola-4,6-dien-24-oic acid;3-Oxo-4,6-choladienoate;UNII-C7WV6M12MR;3-oxo-4,6-choldienoic acid;SCHEMBL605024;CHEBI:88112;3-Oxo-4,6-choladien-24-oate;DTXSID70415288;HY-N9944;AKOS030240903;AT30054;MS-25963;PD164951;CS-0226413;Q27160058;"(R)-4-((8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid"

Chemical Property of 3-Oxochola-4,6-dien-24-oic Acid

Chemical Property:

• Vapor Pressure: 3.55E-13mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 541.8°C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 295.6°C
• PSA: 54.37000
• Density: 1.12g/cm³
• LogP: 5.41140
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 370.25079494
• Heavy Atom Count: 27
• Complexity: 704

Purity/Quality:

98% ^*data from raw suppliers

3-Oxo-4,6-choladien-24-oicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@]34C)C
• Uses: 3-Oxo-4,6-choladien-24-oic Acid is an intermediate in the synthesis of various bile acids.

Technology Process of 3-Oxochola-4,6-dien-24-oic Acid

There total 4 articles about 3-Oxochola-4,6-dien-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: 87.0%

cholan-4,6-dien-3-one-24-al (944409-56-7) → 3-Oxochola-4,6-dien-24-oic acid (88179-71-9)

Guidance literature:

With sodium dichromate; sulfuric acid; water; In acetone; at 0 ℃; for 2h;

Reference yield: 42.0%

4β-bromo-7α-formyloxy-3-oxo-5β-cholanic acid (106351-13-7) → 3-Oxochola-4,6-dien-24-oic acid (88179-71-9) + 7α-formyloxy-3-oxo-4-cholenic acid (106351-14-8)

Guidance literature:

With sodium acetate; 2-oxo-propionic acid; hydrazine carboxamide; Yield given. Multistep reaction; 1.) water, AcOH, 60 deg C, 30 min, then room temp., 1 h ; 2.) water, AcOH, room temp., overnight;

Reference yield: 32.0%

ursodeoxycholic acid (128-13-2) → 3-Oxochola-4,6-dien-24-oic acid (88179-71-9) + (R)-4-((3R,5R,7S,8R,9S,10S,13R,14S,17R)-7-hydroxy-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid + 7β-hydroxy-3-oxochol-4-en-24-oic acid

Guidance literature:

In water; at 37 ℃; for 120h; grown cells of the bacterium Alcaligenes recti (enzymic methylation);

DOI:10.1016/0039-128X(93)90057-T

upstream raw materials:

ursodeoxycholic acid

4β-bromo-7α-formyloxy-3-oxo-5β-cholanic acid

7α-formyloxy-3-oxo-5α-cholanic acid

cholan-4,6-dien-3-one-24-al

Refernces

• 1、 Mazumder, Ipsita,Mahato, Shashi B.. "Bile acid transformations by Alcaligenes recti". . p. 79 - 86. Retrieved 2007/10/02.