Apocholic acid

Base Information

• Chemical Name: Apocholic acid
• CAS No.: 641-81-6
• Molecular Formula: C24H38 O4
• Molecular Weight: 390.62
• NSC Number: 31615,18170
• UNII: MZW7515V5Z
• DSSTox Substance ID: DTXSID00214307
• Nikkaji Number: J1.718C
• Wikipedia: Apocholic_acid
• Wikidata: Q4780126
• Metabolomics Workbench ID: 36464
• Mol file: 641-81-6.mol

Synonyms:Apocholic acid;641-81-6;3alpha,12alpha-Dihydroxy-5beta-chol-8(14)-en-24-oic acid;Apocholicacid;NSC 18170;NSC 31615;BRN 3222755;UNII-MZW7515V5Z;MZW7515V5Z;(4R)-4-[(3R,5R,9R,10S,12S,13R,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;NSC-18170;NSC-31615;3-alpha,12-alpha-Dihydroxy-5-beta-chol-8(14)-en-24-oic acid;3.alpha.,12.alpha.-Dihydroxy-5.beta.-chol-8(14)-en-24-oic acid;5-beta-Chol-8(14)-en-24-oic acid, 3-alpha,12-alpha-dihydroxy-;5.beta.-Chol-8(14)-en-24-oic acid, 3.alpha.,12.alpha.-dihydroxy-;Chol-8(14)-en-24-oic acid, 3,12-dihydroxy-, (3.alpha.,5.beta.,12.alpha.)-;4-10-00-01817 (Beilstein Handbook Reference);3alpha,12alpha-Dihydroxy-5beta,8(14)-cholen-24-oic acid;5beta-Chol-8(14)-en-24-oic acid, 3alpha,12alpha-dihydroxy-;Chol-8(14)-en-24-oic acid, 3,12-dihydroxy-, (3-alpha,5-beta,12-alpha)-;WLN: L E5 B666TJ A1 DQ E1 FY1&2VQ OQ;5.beta.-Chol-8(14)-en-24-oic acid,12.alpha.-dihydroxy-;Chol-8(14)-en-24-oic acid,12-dihydroxy-, (3.alpha.,5.beta.,12.alpha.)-;Apo-CA;.alpha.-Apocholic acid;bmse000733;SCHEMBL9464317;CHEBI:79877;DTXSID00214307;NSC18170;NSC31615;LMST04010224;AKOS015894000;LS-53095;3,12-Dihydroxychol-8(14)-en-24-oic acid #;Q4780126;5beta,8(14)-Cholen-24-oic acid-3alpha,12alpha-diol;3alpha,12alpha-Dihydroxy-5beta-chol-8(14)en-24-oic acid;3alpha, 12alpha-dihydroxy-5beta-chol-8(14)-en-24-oic acid;5.BETA.-CHOL-8(14)-ENIC ACID, 3.ALPHA.,12.ALPHA.-DIHYDROXY-;(4R)-4-((3R,9R,10S,12S,13R,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Chemical Property of Apocholic acid

Chemical Property:

• Vapor Pressure: 6.75E-15mmHg at 25°C
• Melting Point: 175-176 °C(lit.)
• Refractive Index: 1.4460 (estimate)
• Boiling Point: 560.5°C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 306.8°C
• PSA: 77.76000
• Density: 1.17g/cm³
• LogP: 4.54210
• Water Solubility.: 0.8g/L(15 oC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 390.27700969
• Heavy Atom Count: 28
• Complexity: 670

Purity/Quality:

99% ^*data from raw suppliers

ApocholicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2=C3CCC4CC(CCC4(C3CC(C12C)O)C)O
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CCC2=C3CC[C@@H]4C[C@@H](CC[C@@]4([C@H]3C[C@@H]([C@]12C)O)C)O
• Uses: Apocholic Acid which is derived from Cholic Acid (C432600), which is a choleretic produced by and isolated from liver cells.

Technology Process of Apocholic acid

There total 18 articles about Apocholic 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:

cholic acid (81-25-4) → 3α,12α-dihydroxy-5β-chol-8(14)-en-24-oic acid (641-81-6)

Guidance literature:

With acetone; zinc(II) chloride;

DOI:10.1021/ja01214a066

Reference yield:

3α.12α-dihydroxy-5β-choladien-(7.14)-oic acid-(24) → 3α,12α-dihydroxy-5β-chol-8(14)-en-24-oic acid (641-81-6)

Guidance literature:

With palladium on activated charcoal; acetic acid; Hydrogenation;

DOI:10.1039/jr9360000462

Reference yield:

12α-hydroxy-3α-acetoxy-5β-cholen-(7)-oic acid-(24)-methyl ester (439696-06-7) → 3α,12α-dihydroxy-5β-chol-8(14)-en-24-oic acid (641-81-6)

Guidance literature:

With hydrogen; acetic acid; platinum; Erwaermen des Reaktionsprodukts mit methanol. Kalilauge;

DOI:10.1002/hlca.19470300620

upstream raw materials:

chloroform

methyl 3α,12α-dihydroxy-5β-chol-14-en-24-oate

cholic acid

12α-hydroxy-3α-acetoxy-5β-cholen-(7)-oic acid-(24)-methyl ester

Downstream raw materials:

diacetoxy-3α,12α,5β cholene-8,14 oate-24 de methyle

benzoyloxy-3α,5β cholene-8,14 hydroxy-12α morpholamido-24

C₄₂H₅₃NO₆

3α,12α-dihydroxy-5β-chol-8(14)-en-24-ol

Refernces

• 1、 Nonappa,Maitra, Uday. "Synthesis, aggregation behavior and cholesterol solubilization studies of 16-epi-pythocholic acid (3α,12α,16β-trihydroxy-5β-cholan-24-oic acid)". experimental part. p. 506 - 512. Retrieved 2010/06/21.