19043-66-4

Basic information

• Product Name: 5-Hydroxycholestan-4-one
• Synonyms: 5-Hydroxycholestan-4-one;5-Hydroxy-5α-cholestan-4-one
• CAS NO: 19043-66-4
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 0
• Mol File: 19043-66-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Hydroxycholestan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxycholestan-4-one(19043-66-4)
• EPA Substance Registry System: 5-Hydroxycholestan-4-one(19043-66-4)

Safety Data

• Hazardous Substances Data: 19043-66-4(Hazardous Substances Data)

Upstream product

• 108990-30-3 3,3-ethanediyldimercapto-5α-cholestane-4α,5-diol 
• 14163-15-6 4α,5α-dihydroxycholestan-3-one 
• 601-57-0 Cholest-4-en-3-one 
• 16732-86-8 cholest-4-ene 
• 23044-74-8 4β,5β-epoxycholestane-3-one 
• 6079-19-2 (4,5)α-epoxy-5α-cholestan 
• 20233-47-0 4β,5-dihydroxy-5α-cholestane 
• 19536-21-1 cholestane-4α,5α-diol 

Downstream Products

• 116780-56-4 4β-(toluene-4-sulfonyloxy)-5α-cholestan-5-ol 
• 20233-47-0 4β,5-dihydroxy-5α-cholestane 

Relevant articles and documents

Studies of the synthesis of biomarkers. XI. Synthesis of 4,5-secocholestane and 4-methyl-4,5-secocholestane

4,5-Secocholestane (1a) and 4-methyl-4,5-secocholestane (1b) were synthesized from cholesterol (2) in five and seven steps, respectively. The key intermediate, 5-oxo-4,5-secocholestan-4-al (7) was reduced by the Clemmensen method to afford 1a. Meanwhile, 7 underwent selective Wittig reaction, Clemmensen reduction, and hydrogenation to give another target molecule, 1b. The structure of an unknown biomarker was shown to be different from the proposed la by gas Chromatographic and mass spectrometric comparison.

Steroidal N-Nitroamines. Part 1. Denitroamination of Steroidal 4β-,6β-,7α-, and 7β-Nitroamines

The α-hydroxy-nitroamines 6β-nitroamino-5α-cholestane-3β,5α-diol (26) and 6β- and 4β-nitroamino-5α-cholestan-5α-ol (27) and (30) have been prepared by reactions of cholest-5-en-3β-yl formate, cholest-5-ene, and cholest-4-ene with nitrous acid and boron trifluoride-ether complex, and subsequent treatment with sodium borohydride.The nitroamines (12) and (25), obtained by nitrosation of the corresponding oximes, undergo similar reduction to yield 6β-nitroamino-5α-cholestan-3β-yl acetate (32) and the 7β- and 7α-nitroaminocholest-5-en-3β-yl acetates (36) and (38).The results of denitroamination reactions of these nitroamines, performed with acetic anhydride and pyridine, are consistent with a mechanism involving a nitrous oxide-separated ion-pair intermediate (6).The nitroamines (26), (27), and (30) gave the corresponding 5α- and 4α-oxirans (28), (29), and (31) by intramolecular nucleophilic substitution.The nitroamine (32) yields, by a hydrogen β-elimination, the acetyl derivatives of cholest-4-en-3β-ol (33), cholest-5-en-3β-ol (34), and cholest-6-en-3β-ol (35).The acetates of cholest-5-ene-3β,7β-diol (37) and cholest-5-ene-3β,7α-diol(39) were obtained from the 7β- and 7α-nitroamines (36) and (38) through substitution by a counter-ion, a total retention of configuration for the 7α-nitroamine and 14percent inversion for the 7β-isomer being observed.