20α,22R-Dihydroxycholesterol

20α,22R-Dihydroxycholesterol

Names
IUPAC name (3β)-Cholest-5-ene-3,20,22-triol
Identifiers
ChemSpider	7977916
Jmol interactive 3D	Image
PubChem	9802154
InChI InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24?,25-,26-,27+/m0/s1 Key: ISBSSBGEYIBVTO-SDRJTJMFSA-N InChI=1/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24?,25-,26-,27+/m0/s1 Key: ISBSSBGEYIBVTO-SDRJTJMFBP
SMILES OC(CCC(C)C)[C@@](O)(C)[C@H]2CC[C@H]1[C@H]3[C@H](CC[C@@]12C)[C@@]4(C(=C/C3)\C[C@@H](O)CC4)C
Properties
Chemical formula	C27H46O3
Molar mass	418.652 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

20α,22R-Dihydroxycholesterol, or (3β)-cholest-5-ene-3,20,22-triol 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

• 22R-Hydroxycholesterol
• 27-Hydroxycholesterol

References

1. 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. 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.