5beta-Cholane

Base Information

• Chemical Name: 5beta-Cholane
• CAS No.: 80373-86-0
• Molecular Formula: C₂₄H₄₂
• Molecular Weight: 330.597
• UNII: 6EF0441D4P
• Nikkaji Number: J74.706H
• Wikipedia: Cholane
• Metabolomics Workbench ID: 53789
• Mol file: 80373-86-0.mol

Synonyms:5beta-cholane;80373-86-0;cholane;Cholane, 5-beta;Cholane [MI];6EF0441D4P;5beta(H)-Cholane;UNII-6EF0441D4P;(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-pentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene;5-beta-Cholane;5.BETA.-CHOLANE;Cholane, (5.beta.)-;CHOLANE, 5-.BETA.;CHEBI:20664

Chemical Property of 5beta-Cholane

Chemical Property:

• Boiling Point: 402.7±12.0 °C(Predicted)
• PSA: 0.00000
• Density: 0.920±0.06 g/cm3(Predicted)
• LogP: 7.47160
• XLogP3: 9.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 330.328651340
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

99% ^*data from raw suppliers

5β-Cholane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCCC4)C)C
• Isomeric SMILES: CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCCC4)C)C
• Uses: 5β-Cholane is an activator of the farnesol X receptor (FXR) and can potentially be used as a pharmaceutical agent for treatment of cholesterol and lipid-related diseases.

Technology Process of 5beta-Cholane

There total 33 articles about 5beta-Cholane 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:

methyl 5β-cholan-24-oate (2204-14-0) → 5β-Cholan (80373-86-0,548-98-1)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; sodium; In benzene;

DOI:10.1021/ja00823a065

Reference yield:

24-hydroxycholane (3110-99-4) → 5β-Cholan (80373-86-0,548-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride; N,N-dimethyl-aniline; benzene

2: lithium alanate; tetrahydrofuran

With tetrahydrofuran; lithium aluminium tetrahydride; thionyl chloride; N,N-dimethyl-aniline; benzene;

DOI:10.1007/BF00900839

Reference yield:

cholanic acid (25312-65-6) → 5β-Cholan (80373-86-0,548-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄; diethyl ether

2: thionyl chloride; N,N-dimethyl-aniline; benzene

3: lithium alanate; tetrahydrofuran

With tetrahydrofuran; lithium aluminium tetrahydride; thionyl chloride; diethyl ether; N,N-dimethyl-aniline; benzene;

DOI:10.1007/BF00900839

upstream raw materials:

5β-cholan-24-yl chloride

24-(toluene-4-sulfonyloxy)-5β-cholane

methyl 5β-cholan-24-oate

24-(Methylmercapto-thiocarbonyloxy)-5β-cholan