5beta-Cholestane-3alpha,7alpha,12alpha-triol

Base Information

• Chemical Name: 5beta-Cholestane-3alpha,7alpha,12alpha-triol
• CAS No.: 547-96-6
• Molecular Formula: C27H48O3
• Molecular Weight: 420.67
• DSSTox Substance ID: DTXSID70969998
• Nikkaji Number: J40.089K
• Wikidata: Q28529721
• Pharos Ligand ID: XFB5CATB2WFG
• Metabolomics Workbench ID: 36717
• ChEMBL ID: CHEMBL4468145
• Mol file: 547-96-6.mol

Synonyms:3,7,12-trihydroxycholestane;3,7,12-trihydroxycoprostane;3,7,12-trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomer;3,7,12-trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomer;3,7,12-trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomer;3alpha, 7alpha,12alpha-trihydroxy-5beta-cholestane;5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol;5beta-cholestane-3alpha,7alpha,12alpha-triol;chtriol;trihydroxycoprostane

Chemical Property of 5beta-Cholestane-3alpha,7alpha,12alpha-triol

Chemical Property:

• Vapor Pressure: 1.06E-13mmHg at 25°C
• Melting Point: 180-181oC
• Boiling Point: 535.5°C at 760 mmHg
• PKA: 14.65±0.70(Predicted)
• Flash Point: 222.8°C
• PSA: 60.69000
• Density: 1.051g/cm³
• LogP: 5.41020
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 420.36034539
• Heavy Atom Count: 30
• Complexity: 605

Purity/Quality:

97% ^*data from raw suppliers

Trihydroxycoprostane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
• Uses: A sterol, similar to cholesterol and is a substrate for the sterol 27-hydroxylase enzyme in the bile salt synthetic pathway. The accumulation of this compound in urine can manifest as jaundice or, in more extreme cases, is a sign of Xanthomatosis.

Technology Process of 5beta-Cholestane-3alpha,7alpha,12alpha-triol

There total 10 articles about 5beta-Cholestane-3alpha,7alpha,12alpha-triol 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: 95.0%

(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hex-4-enyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol → 5β-Cholestane-3α,7α,12α-triol (547-96-6)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In dichloromethane; for 4h; Irradiation;

DOI:10.1016/S0039-128X(97)00010-X

Reference yield: 60.0%

3-methylbutyric acid (503-74-2) + cholic acid (81-25-4) → 5β-Cholestane-3α,7α,12α-triol (547-96-6)

Guidance literature:

With sodium methylate; In methanol; for 24h; Electrolysis; Cooling with ice;

Reference yield:

3α,7α,12α-trihydroxy-5β-cholestan-24-one (97925-10-5) → 5β-Cholestane-3α,7α,12α-triol (547-96-6)

Guidance literature:

With sodium hydroxide; hydrazine; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol;

DOI:10.1093/oxfordjournals.jbchem.a126906

upstream raw materials:

3-methylbutyric acid

cholic acid

3α,7α,12α-trihydroxy-5β-cholestan-24-one

Downstream raw materials:

7α,12α-dihydroxy-5β-cholestan-3-one

Refernces

• 1、 Dayal,Ertel,Rapole,Asgaonkar,Salen. "Rapid hydrogenation of unsaturated sterols and bile alcohols using microwaves". . p. 451 - 454. Retrieved 2007/10/03.