19043-54-0

Usage

Classification

Ketone derived from cholesterol

Origin

Natural metabolite found in the human body

Biological Significance

Potential marker for metabolic disorders and diseases

Research Focus

Cholesterol Metabolism: Studied for its roles in cholesterol metabolism
Biomarker: Investigated as a biomarker for liver and gallbladder diseases
Therapeutic Potential: Explored for therapeutic applications, including:
Inhibition of 17β-hydroxysteroid dehydrogenase type 10 activity

Medical and Biochemical Relevance

Compound of interest for diagnostic and therapeutic purposes in medicine and biochemistry.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1912-53-4 6-nitrocholest-5-ene 
• 66014-22-0 6β-Chloro-5-hydroxy-5α-cholestane 
• 333-20-0 potassium thioacyanate 
• 20230-22-2 5,6β-epoxy-5β-cholestane 

Downstream Products

• 481-21-0 cholestane 
• 570-46-7 5α-cholestan-6-one 

Relevant academic research and scientific papers

Microwave-assisted transformation of α,β- and β,γ-unsaturated nitroalkenes into carbonyl compounds

Vinyl and allylic nitroalkenes have been converted into the corresponding carbonyl compounds in good yield using tin(II) chloride dihydrate under microwave irradiation.

Recation of Nitro-alkenes with Iodotrimethylsilane: A New Method for the Conversion of Vinyl Nitrosteroids to Ketosteroids

Iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide effects the reduction of nitro-alkenes (1a-e) and (5) at -5 to O deg C to furnish the ketones (2a-e) and (6) respectively as the major products.

Synthesis of Cholestenothiazoles and Cholestanooxazolidine

4β,5-Epoxy-5β-cholestan-3-one (I) reacts with thiourea to afford 5β-hydroxycholest-3-eno-2'-aminothiazole (II) while with thiacetamide it furnishes 3,5-cholestadieno-2'-methylthiazole (III) and 5β-hydroxycholest-3-eno-2'-methylthiazole (IV). 6β-Chloro-5-hydroxy-5α-cholestane (V) on treatment with KSCN in dimethylformamide gives cholesta-4,6-diene (VI), 5α-chloestan-6-one (VII), 5-hydroxy-5α-cholestan-6α-yl isothiocyanate (VIII), 5-hydroxy-5α-cholestan-6-one (IX) and 5α-cholestano-2'-thiooxooxazolidine (X).The structures of these compounds have been established on the basis of spectral properties, analytical data and also by direct comparison with authentic samples where available.

Reactions of steroidal 5,6-epoxides and cyclohexene oxide with aluminum alkoxides

The isomeric 5,6α- and 5,6β-epoxycholestanes, in addition to an analogous series of compounds substituted at C-3 with hydroxy (α or β stereochemistry) or ethylene ketal groups, have been treated with aluminum isopropoxide or tert-butoxide.The latter series of reactions did not give identifiable material, but aluminum isopropoxide gave products derived from epoxide opening and rearrangement in all cases.With epoxides unsubstituted at C-3, aluminum isopropoxide functioned as a Lewis acid in promoting epoxide rearrangements.In the presence of a C-3 alcohol function, additional products were obtained arising from fragmentation of the C-4,C-5 bond, or from β-elimination of the epoxide involving the loss of a C-7 hydrogen.Meerwein-Pondorff reduction of product carbonyl groups was also observed.C-3 ketal substituted epoxides were rearranged cleanly to 6-hydroxy-Δ4-3-ketones.Cyclohexene oxide reacted with aluminum isopropoxide (but not with tert-butoxide) to give two products arising from epoxide addition reactions.Structures for these products are proposed based on their 13C nmr spectra, and a possible route for their formation is presented.None of the epoxides examined in this study reacted with magnesium methoxide.