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

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

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

Proximal ligand electron donation and reactivity of the cytochrome P450 ferric-peroxo anion

CYP125 from Mycobacterium tuberculosis catalyzes sequential oxidation of the cholesterol side-chain terminal methyl group to the alcohol, aldehyde, and finally acid. Here, we demonstrate that CYP125 simultaneously catalyzes the formation of five other products, all of which result from deformylation of the sterol side chain. The aldehyde intermediate is shown to be the precursor of both the conventional acid metabolite and the five deformylation products. The acid arises by protonation of the ferric-peroxo anion species and formation of the ferryl-oxene species, also known as Compound I, followed by hydrogen abstraction and oxygen transfer. The deformylation products arise by addition of the same ferric-peroxo anion to the aldehyde intermediate to give a peroxyhemiacetal that leads to C-C bond cleavage. This bifurcation of the catalytic sequence has allowed us to examine the effect of electron donation by the proximal ligand on the properties of the ferric-peroxo anion. Replacement of the cysteine thiolate iron ligand by a selenocysteine results in UV-vis, EPR, and resonance Raman spectral changes indicative of an increased electron donation from the proximal selenolate ligand to the iron. Analysis of the product distribution in the reaction of the selenocysteine substituted enzyme reveals a gain in the formation of the acid (Compound I pathway) at the expense of deformylation products. These observations are consistent with an increase in the pKa of the ferric-peroxo anion, which favors its protonation and, therefore, Compound I formation.

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.

Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs

In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3β-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxycholesterol and 16-oxo-5-cholestene-3β,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3β-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3β-hydroxy-5-cholestenoate were 7α-hydroxylated in a copper-catalyzed reaction with ert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7β-epimers were obtained as side products. Labeled 3β, 7α-dihydroxy-5-cholenic acid was prepared in the same way from 3β-hydroxy-5-[2,2,4,4,23-2H5]-cholenoic acid. The 3-oxo-Δ4 analogs of the 3β-hydroxy-Δ5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroids and the methylated acids are given for all compounds. (Steroids 58:119-125, 1993).

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.

Composition comprising an oxygenated cholesterol and use thereof for topical treatment of diseases

The invention is directed to a pharmaceutical composition comprising an oxygenated cholesterol and a penetration-enhancing agent which is useful for topical application to the skin of a patient suffering from a proliferative skin disease characterized by geminative cells having a rapid rate of replication, e.g. psoriasis. The composition comprises an effective amount for the inhibition of germinative cell mitosis of an oxygenated cholesterol, e.g. 26-hydroxycholesterol, or a pharmaceutically effective derivative thereof e.g. an ester or ether. The invention is further directed to a method of treating a patient suffering from said skin disease comprising applying to the effected skin said therapeutic composition. The invention is also directed to the topical application of these compositions to the skin to decrease inflammation.