Lithocholenic acid

Base Information

• Chemical Name: Lithocholenic acid
• CAS No.: 1053-37-8
• Molecular Formula: C24H38 O3
• Molecular Weight: 374.564
• UNII: BAO73Q70IY
• DSSTox Substance ID: DTXSID301347234
• Nikkaji Number: J1.784.042H
• Wikidata: Q27274569
• Metabolomics Workbench ID: 36451
• ChEMBL ID: CHEMBL3138720
• Mol file: 1053-37-8.mol

Synonyms:Lithocholenic acid;1053-37-8;BAO73Q70IY;3alpha-Hydroxy-5beta-chol-11-en-24-oic Acid;UNII-BAO73Q70IY;11-Cholenic acid, 3alpha-hydroxy-;11,(5beta)-Cholenic acid-3alpha-ol;(4R)-4-[(3R,5R,8S,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;LITHOCHOL-11-ENIC ACID;CHOL-11-EN-24-oic acid, 3-hydroxy-, (3alpha,5beta)-;CHEMBL3138720;SCHEMBL22855362;CHEBI:166736;DTXSID301347234;LMST04010210;AKOS040752612;11-CHOLENIC ACID, 3.ALPHA.-HYDROXY-;Q27274569;3.ALPHA.-HYDROXY-5.BETA.-CHOL-11-EN-24-OIC ACID;CHOL-11-EN-24-OIC ACID, 3-HYDROXY-, (3.ALPHA.,5.BETA.)-

Chemical Property of Lithocholenic acid

Chemical Property:

• PSA: 57.53000
• LogP: 5.28310
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 374.28209507
• Heavy Atom Count: 27
• Complexity: 613

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C=CC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(C=C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C

Technology Process of Lithocholenic acid

There total 32 articles about Lithocholenic 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%

Lithocholic acid (434-13-9) → lithocholenic acid (1053-37-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 60 - 70 ℃; Inert atmosphere;

DOI:10.1016/j.steroids.2017.06.009

Reference yield:

ethanol (64-17-5) + 3α,11α-dihydroxy-12-oxo-5β-cholan-24-oic acid + hydrazine hydrate (7803-57-8,79785-97-0) → Lithocholic acid (434-13-9) + 3α,11α-dihydroxy-5β-cholan-24-oic acid (94776-83-7) + lithocholenic acid (1053-37-8)

Guidance literature:

Erhitzen des Reaktionsprodukts mit aethanol. Natriumaethylat und wenig Hydrazin-hydrat auf 200grad;

Reference yield:

→ lithocholenic acid (1053-37-8)

Guidance literature:

With sodium ethanolate; hydrazine hydrate; at 190 - 200 ℃;

DOI:10.1021/ja01858a059

upstream raw materials:

1-methyl-4-nitrosobenzene

3-keto-5β-chol-11-enic acid

methyl 3-oxo-5β-chol-11-en-24-oate

9(11),(5β)-cholenic acid-3α-ol-12-one

Downstream raw materials:

methyl 3α-acetoxy-5β-chol-11-ene-24-oate

3β-acetoxy-5β-cholen-(11)-oic acid-(24)-methyl ester