1753-61-3

Basic information

• Product Name: 2α,3α-Epoxy-5α-cholestane
• Synonyms: 2α,3α-Epoxy-5α-cholestane
• CAS NO: 1753-61-3
• Molecular Formula: C₂₇H₄₆O
• Molecular Weight: 386.65354
• Mol File: 1753-61-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2α,3α-Epoxy-5α-cholestane(CAS DataBase Reference)
• NIST Chemistry Reference: 2α,3α-Epoxy-5α-cholestane(1753-61-3)
• EPA Substance Registry System: 2α,3α-Epoxy-5α-cholestane(1753-61-3)

Safety Data

• Hazardous Substances Data: 1753-61-3(Hazardous Substances Data)

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 13901-19-4 cholest-2-ene 
• 80-97-7 Cholestanol 
• 3381-52-0 3β-(toluene-4-sulfonyloxy)-5α-cholestane 
• 1452-34-2 2α-bromo-5α-cholestan-3-one 
• 570-73-0 5α-Cholest-2-ene 
• 57-88-5 cholesterol 
• 51154-61-1 neocholesteryl bromide 
• 2309-03-7 (3R,5S,8R,9S,10S,13R,14S,17R)-3-bromo-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene 
• 63866-20-6 3β-bromo-5α-cholestan-6-one 
• 1056-93-5 3β-chloro-5α-cholestan-6-one 
• 21072-86-6 3α-chloro-5α-cholestan-6-one 
• 5847-30-3 3α-chloro-5α-cholestane 

Downstream Products

• 116670-99-6 2β-(toluene-4-sulfonyloxy)-5α-cholestan-3α-ol 
• 16126-32-2 (2β-3α-5α)-cholestane-2,3-diol 
• 57708-77-7 (2S,3S,5S,8R,9S,10S,13R,14S,17R)-2-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 2042-08-2 2β-bromo-5α-cholestan-3-one 
• 1031890-76-2 2β-(N-benzylamino)-3α-hydroxy-5α-cholestane 
• 57708-78-8 (2S,5S,8R,9S,10S,13R,14S,17R)-2-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one 
• 57708-79-9 (2S,3R,5S,8R,9S,10S,13R,14S,17R)-2-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-3,10,13-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 10146-89-1 5α-Cholestan-2α,3α-diol 

Relevant articles and documents

The Octant Rule VIII. Variable Temperature Circular Dichroism Spectra of α-Methyl- and Methoxyl-Substituted 5α-Cholestan-2- and -3-ones.

2α- and 2β-methyl- and methoxy-5α-cholestan-3-ones and 3α- and 3β-methyl- and methoxy-5α-cholestan-2-ones have been synthesized and their variable temperature circular dichroism spectra obtained and analyzed.Rotatory strength (R) values for α-axial and equatorial CH3 and OCH3 groups are determined by difference measurements with the parent ketone.The (small) equatorial CH3 R-values do not consistently follow the Octant Rule.Axial OCH3 groups do not obey the Octant Rule ("anti-octant" behavior) and impose a bathochromic shift on the C=O n-?* transition.Equatorial OCH3 groups do not consistently follow octant or "anti-octant" behavior.

Modification in the side chain of solomonsterol A: Discovery of cholestan disulfate as a potent pregnane-X-receptor agonist

Seven synthetic analogues of the PXR (pregnane-X-receptor) potent natural agonist solomonsterol A were prepared by total synthesis. Their activity toward PXR was assessed by transactivation and RT-PCR assays. The study discloses cholestan disulfate (8) as a new, simplified agonist of PXR. By in vitro studies on hepatic cells we have demonstrated that this compound is a potent PXR agonist and functional characterization in human macrophages and hepatic stellate cells provided evidence that cholestan disulfate (8) has the ability to modulate the immune response triggered by bacterial endotoxin as well as to counter-activate hepatic stellate cell activation induced by thrombin. Because inhibition of immune-driven circuits might have relevance in the treatment of inflammation and liver fibrosis, the present data support the development of cholestan disulfate (8) in preclinical models of inflammatory diseases. The Royal Society of Chemistry 2012.

Regioselective enzymatic acylation of vicinal diols of steroids

Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.