570-91-2

Basic information

• Product Name: (3beta)-3-hydroxycholestan-6-one
• Synonyms: cholestan-6-one, 3-hydroxy-, (3beta)-
• CAS NO: 570-91-2
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 402.6529
• Mol File: 570-91-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 501.3°C at 760 mmHg
• Flash Point: 212.4°C
• Density: 1g/cm³
• Vapor Pressure: 3.78E-12mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (3beta)-3-hydroxycholestan-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta)-3-hydroxycholestan-6-one(570-91-2)
• EPA Substance Registry System: (3beta)-3-hydroxycholestan-6-one(570-91-2)

Safety Data

• Hazardous Substances Data: 570-91-2(Hazardous Substances Data)

Upstream product

• 60203-18-1 (24R)-3β-acetoxy-24-ethylcholest-4-en-6-one 
• 82048-76-8 3-β-hydroxy-6-nitrocholest-5-ene 
• 14956-06-0 3β-acetoxy-5-amino-5α-cholestan-6-one 
• 57-88-5 cholesterol 
• 54339-68-3 4-cholestene-3,6-dione 
• 104596-45-4 3β-acetoxy-cholest-4-en-6-one 
• 6580-09-2 3β-acetoxy-5α-hydroxycholestan-6-one 
• 1256-31-1 3β-acetoxy-5,6-epoxycholestane 
• 14956-05-9 5α-aminocholestane-3β,6β-diol 3-acetate 
• 15086-56-3 5α-azidocholestane-3β,6β-diol 3-acetate 
• 1256-31-1 5,6-β-epoxycholesteryl acetate 

Relevant articles and documents

A Convenient Method for the Synthesis of 3β-Hydroxy 4-En-6-one Steroids

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H-Atom Abstraction vs Addition: Accounting for the Diverse Product Distribution in the Autoxidation of Cholesterol and Its Esters

We recently communicated that the free-radical-mediated oxidation (autoxidation) of cholesterol yields a more complex mixture of hydroperoxide products than previously appreciated. In addition to the epimers of the major product, cholesterol 7-hydroperoxide, the epimers of each of the regioisomeric 4- and 6-hydroperoxides are formed as is the 5α-hydroperoxide in the presence of a good H-atom donor. Herein, we complete the story by reporting the products resulting from competing peroxyl radical addition to cholesterol, the stereoisomeric cholesterol-5,6-epoxides, which account for 12% of the oxidation products, as well as electrophilic dehydration products of the cholesterol hydroperoxides, 4-, 6-, and 7-ketocholesterol. Moreover, we interrogate how their distribution - and abundance relative to the H-atom abstraction products - changes in the presence of good H-atom donors, which has serious implications for how these oxysterols are used as biomarkers. The resolution and quantification of all autoxidation products by LC-MS/MS was greatly enabled by the synthesis of a new isotopically labeled cholesterol standard and corresponding selected autoxidation products. The autoxidation of cholesteryl acetate was also investigated as a model for the cholesterol esters which abound in vivo. Although esterification of cholesterol imparts measurable stereoelectronic effects, most importantly reflected in the fact that it autoxidizes at 4 times the rate of unesterified cholesterol, the product distribution is largely similar to that of cholesterol. Deuteration of the allylic positions in cholesterol suppresses autoxidation by H-atom transfer (HAT) in favor of addition, such that the epoxides are the major products. The corresponding kinetic isotope effect (kH/kD ～ 20) indicates that tunneling underlies the preference for the HAT pathway.

Synthesis of cytotoxic 6E-hydroximino-4-ene steroids: Structure/activity studies

In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioctivity than other structural motifs.