5beta-Cholestan-3-one

Base Information

• Chemical Name: 5beta-Cholestan-3-one
• CAS No.: 601-53-6
• Molecular Formula: C27H46O
• Molecular Weight: 386.662
• European Community (EC) Number: 210-003-0
• UNII: H6B6EPA52O
• DSSTox Substance ID: DTXSID50862211
• Nikkaji Number: J39.845D
• Wikidata: Q27098364
• Metabolomics Workbench ID: 34493
• ChEMBL ID: CHEMBL69851
• Mol file: 601-53-6.mol

Synonyms:5beta-cholestan-3-one

Chemical Property of 5beta-Cholestan-3-one

Chemical Property:

• Melting Point: 62-63 °C
• Boiling Point: 452.9 °C at 760 mmHg
• Flash Point: 219.3 °C
• PSA: 17.07000
• Density: 0.953 g/cm³
• LogP: 7.67680
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly)
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 386.354866087
• Heavy Atom Count: 28
• Complexity: 579

Purity/Quality:

99%, ^*data from raw suppliers

5β-Cholestan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C
• Uses: 5β-Cholestan-3-one is a metabolite of cholesterol and is used to asses the biosynthesis of cholesterol.

Technology Process of 5beta-Cholestan-3-one

There total 85 articles about 5beta-Cholestan-3-one 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: 98.0%

Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5) → coprostanone (601-53-6)

Guidance literature:

With sodium bromate; ruthenium trichloride; tetrabutylammomium bromide; In dichloromethane; water; at 25 ℃; for 1.5h;

DOI:10.1246/bcsj.59.105

Reference yield: 97.0%

3,3-ethylenedioxy-5β-cholestane (25328-53-4) → coprostanone (601-53-6)

Guidance literature:

With Montmorillonite K 10; water; In acetone; for 3h; Heating;

DOI:10.1080/00397919708003385

Reference yield: 96.0%

1,3-dithiane of cholestanone (39854-45-0) → 1,2-dithiolane (557-22-2) + coprostanone (601-53-6)

Guidance literature:

With tetrafluoroboric acid; tris(2,2'-bipyridine)iron(III) perchlorate; In tetrahydrofuran; water; acetonitrile; for 0.0833333h; Ambient temperature;

upstream raw materials:

cholesterol

Cholest-4-en-3-one

epicoprostanol

Coprostanol

Downstream raw materials:

3,3-ethylenedioxy-5β-cholestane

4-(5β-cholestan-3-ylidenehydrazino)-benzoic acid

3-β-benzyl-5-α-cholestane-3-α-ol

epicoprostanol

Refernces

• 1、 Lator, Alexis,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc. "Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones". supporting information. p. 5770 - 5774. Retrieved 2018/03/26.
• 2、 Iida, Takashi,Omura, Kaoru,Sakiyama, Ryou,Kodomari, Mitsuo. "Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis". . p. 45 - 51. Retrieved 2014/03/21.