22R-Hydroxycholesterol
From Wikipedia, the free encyclopedia
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| IUPAC name
(22R)-Cholest-5-ene-3β,22-diol
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| Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2S,3R)-3-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C27H46O2 | |
| Molar mass | 402.653 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol.[1] [2] Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one),[1] [2] the precursor to the steroid hormones.
It is an agonist of the liver X receptor.
See also
[edit ]References
[edit ]- ^ a b CHAUDHURI AC, HARADA Y, SHIMIZU K, GUT M, DORFMAN RI (March 1962). "Biosynthesis of pregnenolone from 22-hydroxycholesterol". The Journal of Biological Chemistry. 237 (3): 703–4. doi:10.1016/S0021-9258(18)60359-X . PMID 13878470.
- ^ a b Hume R, Kelly RW, Taylor PL, Boyd GS (May 1984). "The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone". European Journal of Biochemistry. 140 (3): 583–91. doi:10.1111/j.1432-1033.1984.tb08142.x . PMID 6723652.
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