10146-89-1

Basic information

• Product Name: cholestane-2,3-diol
• CAS NO: 10146-89-1
• Molecular Formula: C₂₇H₄₈O₂
• Molecular Weight: 404.6688
• Mol File: 10146-89-1.mol

Chemical Properties

• Boiling Point: 488.8°C at 760 mmHg
• Flash Point: 199.6°C
• Density: 1.003g/cm³
• Vapor Pressure: 1.33E-11mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: cholestane-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: cholestane-2,3-diol(10146-89-1)
• EPA Substance Registry System: cholestane-2,3-diol(10146-89-1)

Safety Data

• Hazardous Substances Data: 10146-89-1(Hazardous Substances Data)

Upstream product

• 59445-40-8 Acetic acid (2S,3S,5S,10S,13R,17R)-17-(1,5-dimethyl-hexyl)-2-iodo-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 570-73-0 5α-Cholest-2-ene 
• 61010-51-3 Acetic acid (2R,3S,5S,10S,13R,17R)-17-(1,5-dimethyl-hexyl)-2-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 7674-81-9 Acetic acid (2R,3S,5S,10S,13R,17R)-3-acetoxy-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester 
• 1753-61-3 2α,3α-Oxido-5α-cholestan 
• 32212-85-4 (2S,3S,5S,10S,13R,17R)-17-(1,5-Dimethyl-hexyl)-2-iodo-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 2789-50-6 2β,3β-Oxido-5α-cholestane 
• 1753-61-3 2α,3α-epoxy-5α-cholestane 
• 13901-19-4 cholest-2-ene 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 61168-20-5 2β-acetoxy-5α-cholestan-3β-ol 
• 6685-02-5 3α-iodo-5α-cholestan-2β-yl acetate 
• 80235-45-6 Cholestano-<2α,3α-d>-dioxol-2'-on 

Downstream Products

• 1178-00-3 2,3-seco-5α-cholestane-2,3-dicarboxylic acid 
• 123878-78-4 3β-(toluene-4-sulfonyloxy)-5α-cholestan-2β-ol 

Relevant articles and documents

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.

Syntheses of Steroidal trans-Iodo Acetates

The reaction of the following streoidal olefins with iodine-copper(II) acetate in acetic acid afforded the corresponding steroidal trans-iodo acetates: 5α-cholest-1, -2-, and -3-ene; and 5β-cholest-1-, -2-, and -3-ene.

A NEW SYNTHESIS OF CIS-DIOL FROM OLEFIN USING IODINE-COPPER(II) ACETATE

The reaction mixtures of 5α-cholest-2-ene with iodine and copper(II) acetate were converted with potassium hydroxide in methanol-water to give the more hindered 2β, 3β-diol in high yield.Cyclohexene and cycloheptene similarly gave the corresponding cis-diols in good yield.This new synthetic method afforded several advantage over the Prevost reaction.

A new synthesis of cis-diol from alkene using iodine-ammonium cerium(IV) nitrate

The reaction mixtures of 5α-cholest-2-ene with iodine-ammonium cerium(IV) nitrate [CAN(IV)] were converted with potassium hydroxide in methanol-water to give the more hindered 2β,3β-diol in high yield. Cyclohexene and cycloheptene similarly reacted to the corresponding cis-diols in good yield. It was found that this reaction intermediate proceeds to give trans-iodoacetate via trans-iodonitrate. This new synthetic method provided several advantages over the Prevost reaction. Georg Thieme Verlag Stuttgart.

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.

Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane

Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium

AN ALTERNATIVE ROUTE TO 2α,3α-DIOLS FROM 2,3-UNSATURATED 5α-STEROIDS AVOIDING THE USE OF OSMIUM TETRAOXIDE

A method for preparation of 2α,3α-dihydroxy-5α-steroids from 2,3-unsaturated 5α-steroids without the use of OsO4 is described.It involves the sequence of epoxidation, cleavage of the oxirane ring by HI, acetylation, oxidative replacement of iodine by hydroxyl and alkaline hydrolysis (I-IV) without purification of the intermediates.The presence of a 6-keto group does not decrease the yields.The yields are comparable with those obtained by osmylation and the method can find general use, particularly in the synthesis of brassinolide analogs.

Steroids. LXIX. Cyclisation Reactions of Vicinal Substituted Halogen Carbamoyloxy Steroids

Vicinal halogen urethanes of the cholestane, androstane and estratriene series react by heating under solvolytic conditions to cyclic carbonates of the corresponding cis-diols.By heating under basic conditions the same compounds react preferably to 2-oxazolidinones and if the basic conditions are strong enough by hydrolysis of the oxazolidinones to cis-amine alcohols too.Connections between the nature of the substituent at the urethane group or the steric arrangement of the vicinal groups on one hand and the reactivity to ring closure on the other hand are presented.