22R-Hydroxycholesterol

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22R-Hydroxycholesterol
22R-Hydroxycholesterol.svg
Identifiers
PubChem 107724
ChemSpider 96893
Jmol-3D images Image 1
Properties
Molecular formula C27H46O2
Molar mass 402.653 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 hydroxlated 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.

See also[edit]

References[edit]

  1. ^ 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: 703–4. PMID 13878470. 
  2. ^ 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 / FEBS 140 (3): 583–91. doi:10.1111/j.1432-1033.1984.tb08142.x. PMID 6723652.