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22R-Hydroxycholesterol

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Title: 22R-Hydroxycholesterol  
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Subject: 20α,22R-Dihydroxycholesterol, Steroid, Cortodoxone, Cyanoketone, Metyrapone
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22R-Hydroxycholesterol

22R-Hydroxycholesterol
IUPAC name

(3β)-Cholest-5-ene-3,22-diol

Identifiers
PubChem
ChemSpider
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)

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

References

  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.  
  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.  


Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To Cholesterol
From Cholesterol
(to steroids)
Steroid hormones
Corticosteroids
(C21 pregnane)
Mineralocorticoids
Glucocorticoids
Sex steroids
Androgens
(C19 androstane)
Estrogens
(C18 estrane)
Nonhuman
Phytosterols
Ergosterols

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Precursors
Corticosteroids
Sex steroids
Neurosteroids
Others


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