2243-09-6

Basic information

• Product Name: 5α-Cholestane-3,6-dione
• Synonyms: 5α-Cholestane-3,6-dione
• CAS NO: 2243-09-6
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.63706
• Mol File: 2243-09-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 499.2°C at 760 mmHg
• Flash Point: 184.6°C
• Appearance: /
• Density: 0.996g/cm³
• Vapor Pressure: 4.25E-10mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 5α-Cholestane-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5α-Cholestane-3,6-dione(2243-09-6)
• EPA Substance Registry System: 5α-Cholestane-3,6-dione(2243-09-6)

Safety Data

• Hazardous Substances Data: 2243-09-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-18,20-24H,6-16H2,1-5H3/t18-,20+,21-,22+,23+,24-,26-,27-/m1/s1

Upstream product

• 566-88-1 dihydrocholesterone 
• 984-84-9 Cholest-4-ene-3,6-dione 
• 17320-10-4 4β-hydroxycholesterol 
• 570-89-8 6β-hydroxycholest-4-en-3-one 
• 64-19-7 acetic acid 

Downstream Products

• 80-97-7 Cholestanol 
• 15223-09-3 6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 57711-50-9 3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene 
• 604-35-3 Cholesteryl acetate 
• 481-21-0 cholestane 

Relevant articles and documents

P -TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization

A solid support-mediated p-TsOH-catalyzed milder transformative protocol was developed to furnish diverse ring-A and/or ring-B oxo-functionalized steroids. To furnish interesting isomers involving the A/B-ring of biomolecules in a one-pot approach, only solid supports (and not solution!) were found to be effective. p-TsOH/SiO2-oxidation of 4β-hydroxycholesterol, the major oxysterol in human circulation, into a mixture of cholest-4-en-3-one, cholest-4-ene-3,6-dione, and 5α-cholestane-3,6-dione was the starting point for the investigations herein. The reaction protocol was optimized in detail, and efforts were carried out toward gaining an understanding of the mechanistic aspects favoring the solid support, and a possible synergetic catalytic system involving p-TsOH and SiO2 was expected to be a key part. Application of the novel methodology to 4β,7α-dihydroxy steroids resulted in the desired diverse ketosteroids through oxidation/oxidative dehydration, which generalized the process as a facile multi-oxo-functionalization steroidal transformation.

Functionalisation of Saturated Hydrocarbons. Part 6. Selective Oxidation of Steroids and Related Compounds

The oxidation of a series of steroids by the Gif system gives, almost without exception, the 20-ketone as major isolated product.The side-chain cleavage is made more selective by modification of rings A or B.The oxidation of oleana-1,12-diene-3,11-dione has also been studied and the two principal products have been identified.