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

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

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

Downstream Products

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

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.

OXIDATION OF STEROID CONJUGATED DIENES AND STEROID EPOXIDES WITH PYRIDINIUM CHLOROCHROMATE

Pyridinium chlorochromate (PCC) reacts with some conjugated steroid dienes giving unsaturated 1,4-ketols or an unsaturated 1,4-diketone depending on whether the carbon atoms involved in the oxidation are secondary or tertiary carbons.Steroid epoxides characterized by the presence of an epoxidic tertiary carbon atom and a secondary one are transformed into ketols by PCC; only in one case is chlorohydrin formation also observed.The reactivity of epoxides with secondary epoxidic carbon atoms depends on the position of the epoxide function in the steroid molecule.Steroid oxiranes are oxidized to ketones with the loss of a carbon atom of the oxirane ring.The reaction conditions are mild and the yields obtained are satisfactory.

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.