2515-01-7

Usage

General Description

5-Hydroxy-5α-cholestan-3-one is a steroidal compound and a metabolite of cholesterol. It is a highly oxidized form of cholesterol and is an intermediate in the biosynthesis of bile acids. This chemical has been studied for its potential role in cholesterol metabolism and the development of atherosclerosis. It has also been investigated for its potential therapeutic applications in the treatment of cholesterol-related disorders. Additionally, 5-Hydroxy-5α-cholestan-3-one has been identified as a biomarker for certain diseases, including Niemann-Pick disease type C, and is being further researched for its diagnostic and prognostic potential.

Upstream product

• 1256-31-1 Acetic acid (3S,5R,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester 
• 2515-12-0 (4α,5)-epoxy-5α-cholestan-3-one 
• 3347-60-2 cholestane-3β,5α-diol 
• 592509-68-7 1-{2-[(3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-phenyl}-2,2,2-trifluoro-ethanone 

Downstream Products

• 601-57-0 Cholest-4-en-3-one 
• 32232-90-9 [(8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-phosphonic acid dimethyl ester 
• 157920-48-4 3α-phenyl-3β,5α-cholestanediol 
• 157920-47-3 3β-phenyl-3α,5α-cholestanediol 
• 80-97-7 Cholestanol 
• 3347-60-2 cholestane-3β,5α-diol 
• 481-21-0 cholestane 
• 570-96-7 5α-cholestane-3α,5-diol 

Relevant academic research and scientific papers

Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ

We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp3 hydrocarbon tether and a sp2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.

Fragmentation of Alkoxy Radicals: Tandem β-Fragmentation-Cycloperoxyiodination Reaction

The steroidal alcohols 2-cholesten-5α-ol (3), 3-phenyl-2-cholesten-5α-ol (4), and 3αH-2'-oxofurocholestan-5α-ol (5) were prepared in order to test a new tandem β-fragmentation-cycloperoxyiodination reaction.The alkoxy radicals generated by irradiatio

Thiol/Diselenide Exchange for the Generation of Benzeneselenolate Ion. Catalytic Reductive Ring-Opening of α,β-Epoxy Ketones

In the presence of N-acetylcysteine sodium salt, benzeneselenolate ion was generated in situ from diphenyl diselenide via thiol/diselenide and thiol/selenenyl sulfide exchange in aqueous methanol under mild conditions.Benzeneselenolate ion thus formed was efficiently alkylated and arylated to afford alkyl phenyl selenides and aryl phenyl selenides, respectively. α,β-Epoxy ketones were catalytically reduced by benzeneselenolate ion to afford β-hydroxy ketones (aldols) in good yields.The stereospecificity of the reaction was demonstrated in the preparation of optically active β-hydroxy ketones from chiral α,β-epoxy ketones.