3862-25-7

Basic information

• Product Name: (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• Synonyms: (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;7a-Hydroxy-cholestene-3-one;7 alpha-hydroxy-4-cholesten-3-one;(7a)-7-Hydroxycholest-4-en-3-one;7a-Hydroxy-4-cholesten-3-one;7a-Hydroxycholest-4-en-3-one;7-Hydroxy-4-cholesten-3-one;(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-diMethyl-17-((R)-6-Methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• CAS NO: 3862-25-7
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.64
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 3862-25-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 182-184°C
• Boiling Point: 516.7 °C at 760 mmHg
• Flash Point: 218.5 °C
• Appearance: White Solid
• Density: 1.03 g/cm³
• Vapor Pressure: 7.76E-13mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.49±0.70(Predicted)
• CAS DataBase Reference: (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(3862-25-7)
• EPA Substance Registry System: (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(3862-25-7)

Safety Data

• Hazardous Substances Data: 3862-25-7(Hazardous Substances Data)

Usage

Description

7α-hydroxy-4-Cholesten-3-one is a metabolite of 7α-hydroxy cholesterol and an intermediate in the biosynthesis of bile acids. Plasma levels of 7α-hydroxy-4-cholesten-3-one positively correlate with the rate of bile acid synthesis in humans and are increased in patients following ileal resection.

Chemical Properties

White Solid

Uses

7α-Hydroxy-4-cholesten-3-one is a metabolite of Cholesterol (C432501).

Definition

ChEBI: A cholestanoid consisting of a cholesterol core having an oxo group at the 3-position, a C2C bond at the 4,5-position and an alpha-hydroxy group at the 7-position.

InChI:InChI=1/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

Upstream product

• 604-35-3 Cholesteryl acetate 
• 1448262-85-8 7α-formyloxy-4-cholesten-3-one 
• 6544-51-0 cholest-4-en-7α-ol 
• 19317-90-9 7α-hydroxycholest-5-en-3β-yl 3-acetate 
• 809-51-8 7-ketocholesteryl acetate 

Downstream Products

• 1254-03-1 7α,12α-dihydroxy-4-cholesten-3-one 

Relevant articles and documents

Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption

7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3-desoxy-Δ4-7α-formate steroid precursor to form 7α-formyloxy-cholest-4-en-3-one, which was saponified to yield 7α-hydroxy-cholest-4-en-3-one.