700113P

7α-hydroxycholestenone

Avanti Polar Lipids

• Synonym(s): C4; α-HC; α-HC; 7HCO; 7 α-3ox-C; 111107
• Empirical Formula (Hill Notation): C₂₇H₄₄O₂
• CAS Number: 3862-25-7
• Molecular Weight: 400.64
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• description: 7α-hydroxy-4-cholesten-3-one
• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 1 mg (700113P-1mg); pkg of 1 × 10 mg (700113P-10mg)
• manufacturer/tradename: Avanti Polar Lipids
• shipped in: dry ice
• storage temp.: −20°C
• InChI: 1S/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
• InChI key: IOIZWEJGGCZDOL-RQDYSCIWSA-N

Description

General description

7α-Hydroxy-4-cholesten-3-one is an intermediate in the biochemical synthesis of bile acids from cholesterol. Its precursor, 7α-hydroxycholesterol, is produced from cholesterol by hepatic cholesterol 7α-hydroxylase (CYP7A1).[1]It is metabolized by the enzyme 7α-hydroxycholest-4-en-3-one 12α-hydroxylase to 7α,12α-dihydroxycholest-4-en-3-one and then to cholic acid, the major primary bile acid in humans. Alternatively, it can be converted into 5β-cholestane-3α,7α-diol and then to chenodeoxycholic acid, the other major primary bile acid in humans.Serum 7α-hydroxy-4-cholesten-3-one concentrations reflect the activity of the bile acid synthetic pathway. Serum 7α-hydroxy-4-cholesten-3-one values vary during the day as bile acid synthetic rates have a diurnal rhythm.[2]Elevated values are found in patients with bile acid malabsorption and may be useful in the diagnosis of this condition as high values are associated with low SeHCAT retention.[3] The increase in serum 7α-hydroxy-4-cholesten-3-one concentrations reflects the loss of bile acids secondary to bile acid malabsorption or the increased synthesis found in primary bile acid diarrhea associated with impaired negative feedback of CYP7A1 by FGF19.[4]

Application

• Role as a mediator in cholesterol metabolism: 7α-hydroxycholestenone has been implicated in the discussion on oxysterols as cholesterol metabolites that act as significant mediators within biological systems, highlighting its importance in cholesterol metabolism and potential pharmaceutical implications (Mutemberezi et al., 2016).

Packaging

5 mL Amber Glass Screw Cap Vial (700113P-10mg)

5 mL Amber Glass Screw Cap Vial (700113P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable