7-Ketocholesterol

• CAT Number: R009252
• CAS Number: 566-28-9
• Molecular Formula: C27H44O2
• Molecular Weight: 400.64
• Purity: ≥95%
• Synonyms: (3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• InChI: 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/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
• InChIKey: YIKKMWSQVKJCOP-ABXCMAEBSA-N
• SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C

7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].

Reference

[1]. M A Lyons, et al. 7-Ketocholesterol. Int J Biochem Cell Biol. Mar-Apr 1999;31(3-4):369-75.
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[2]. Amelia Anderson, et al. 7-Ketocholesterol in disease and aging. Redox Biol. 2020 Jan;29:101380.
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