19257-21-7

Basic information

• Product Name: 26-Hydroxycholest-4-en-3-one
• Synonyms: 26-Hydroxycholest-4-en-3-one
• CAS NO: 19257-21-7
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 0
• Mol File: 19257-21-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 26-Hydroxycholest-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 26-Hydroxycholest-4-en-3-one(19257-21-7)
• EPA Substance Registry System: 26-Hydroxycholest-4-en-3-one(19257-21-7)

Safety Data

• Hazardous Substances Data: 19257-21-7(Hazardous Substances Data)

Usage

Description

26-Hydroxycholest-4-en-3-one is a cholestanoid, which is a type of steroid compound. It consists of a 3-oxocholest-4-ene structure with a hydroxy substituent at position 26. 26-Hydroxycholest-4-en-3-one is derived from cholesterol and has potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
26-Hydroxycholest-4-en-3-one is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of drugs targeting specific biological pathways.
Used in Research Applications:
In the field of research, 26-Hydroxycholest-4-en-3-one serves as a valuable tool for studying the metabolism and function of cholesterol and its related compounds. It can be used to investigate the role of cholestanoids in various biological processes and diseases.
Used in Chemical Synthesis:
26-Hydroxycholest-4-en-3-one can be used as a starting material for the synthesis of other cholestanoids and related compounds. Its unique structure makes it a versatile building block for creating new molecules with potential applications in various industries.
Used in Analytical Chemistry:
As a cholestanoid, 26-Hydroxycholest-4-en-3-one can be employed as a reference compound in analytical chemistry for the development and validation of methods for the analysis of steroids and related compounds. This can be particularly useful in the fields of environmental monitoring, food analysis, and clinical diagnostics.

Upstream product

• 13095-61-9 26-hydroxycholesterol 
• 137435-82-6 (8S,9S,10R,13R,14S,17R)-17-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 7558-37-4 Kryptogenin 
• 137435-76-8 (R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-heptan-1-ol 
• 57984-04-0 6β-methoxy-3α,5-cyclo-5α-chol-23-en-22-ol 
• 137435-75-7 ethyl (25ξ)-6β-methoxy-3α,5-cyclo-5α-cholestan-26-oate 
• 137436-15-8 ethyl (25ξ,22E)-6β-methoxy-3α,5-cyclo-5α-cholest-22-en-26-oate 
• 137435-78-0 tert-Butyl-[(R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-heptyloxy]-diphenyl-silane 
• 137435-81-5 (8S,9S,10R,13R,14S,17R)-17-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-10,13-dimethyl-1,2,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 137435-80-4 (25ξ)-26-<(tert-butyldiphenylsilyl)oxy>cholest-5-en-3β-yl acetate 
• 601-57-0 Cholest-4-en-3-one 

Downstream Products

• 601-57-0 Cholest-4-en-3-one 
• 137464-55-2 C₃₆H₅₄O₃S₃ 

Relevant articles and documents

Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: Evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen

The Mycobacterium tuberculosis cytochrome P450 enzyme CYP142 is encoded in a large gene cluster involved in metabolism of host cholesterol. CYP142 was expressed and purified as a soluble, low spin P450 hemoprotein. CYP142 binds tightly to cholesterol and its oxidized derivative cholest-4-en-3-one, with extensive shift of the heme iron to the high spin state. High affinity for azole antibiotics was demonstrated, highlighting their therapeutic potential. CYP142 catalyzes either 27-hydroxylation of cholesterol/cholest-4-en-3-one or generates 5-cholestenoic acid/cholest-4-en-3-one-27-oic acid from these substrates by successive sterol oxidations, with the catalytic outcome dependent on the redox partner system used. The CYP142 crystal structure was solved to 1.6 A, revealing a similar active site organization to the cholesterol-metabolizing M. tuberculosis CYP125, but having a near-identical organization of distal pocket residues to the branched fatty acid oxidizing M. tuberculosis CYP124. The cholesterol oxidizing activity of CYP142 provides an explanation for previous findings that ΔCYP125 strains of Mycobacterium bovis and M. bovis BCG cannot grow on cholesterol, because these strains have a defective CYP142 gene. CYP142 is revealed as a cholesterol 27-oxidase with likely roles in host response modulation and cholesterol metabolism.

Biosynthetic studies of marine lipids. 39.1 19-norsterols: The course of c-19 methyl elimination

The biosynthesis of 19-norstanols in the Mediterranean sponge, Axinella polypoides, was investigated through the use of radiotracer experiments. It was found that the conversion of cholesterol (7) to 19-nor-5α-chotestan-3β-ol (8) involved oxidation at C-3 with the distribution of the abstracted hydride from the 3α-position of dietary cholesterol into all of the 19-norstanols of the native mixture. Furthermore, while the efficiency of conversion of Δ5-19-oxygenated sterol precursors 19-hydroxycholesterol (9) and 3β-hydroxycholest-5-en-19-oic acid (10) to 8 was low, the efficiency of the conversion of 19-hydroxycholest-4-en-3-one (23) to 8 was high, suggesting that the principal pathway for 19-norstanol biosynthesis involves oxidative isomerization of a dietary Δ5-3β-hydroxy sterol to the δ4-3-ketone before oxidation at C-19. It was also shown that the conversion of cholesterol to 19-nor-5α-cholestan-3β-ol involves the stereospecific loss of the 4β-hydrogen atom. It was further determined that the biological demethylation pathway is suppressed for dietary sterols bearing an unconventional configuration at C-20 in the hydrocarbon side chain.