:22R-Hydroxycholesterol

{{DISPLAYTITLE:22R-Hydroxycholesterol}}

{{Chembox

| ImageFile = 22R-Hydroxycholesterol.svg

| ImageSize = 200px

| IUPACName = (22R)-Cholest-5-ene-3β,22-diol

| SystematicName = (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

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 17711-16-9

| CASNo_Ref = {{Cascite|changed|EPA}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TJ9HV8VPD2

| ChEBI = 166802

| ChEMBL = 3218924

| PubChem = 107724

| ChemSpiderID = 96893

| SMILES = O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)C(O)CCC(C)C)C)[C@@]3(C)CC4

| InChI = 1/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1

| InChIKey = RZPAXNJLEKLXNO-UKNNTIGFBU

| StdInChI = 1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1

| StdInChIKey = RZPAXNJLEKLXNO-UKNNTIGFSA-N

}}

|Section2={{Chembox Properties

| Formula = C₂₇H₄₆O₂

| MolarMass = 402.653 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol.{{cite journal | vauthors = CHAUDHURI AC, HARADA Y, SHIMIZU K, GUT M, DORFMAN RI | title = Biosynthesis of pregnenolone from 22-hydroxycholesterol | journal = The Journal of Biological Chemistry | volume = 237 | pages = 703–4 | date = March 1962 | issue = 3 | doi = 10.1016/S0021-9258(18)60359-X | pmid = 13878470 | doi-access = free }}{{cite journal |vauthors=Hume R, Kelly RW, Taylor PL, Boyd GS | title = The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone | journal = European Journal of Biochemistry | volume = 140 | issue = 3 | pages = 583–91 |date=May 1984 | pmid = 6723652 | doi = 10.1111/j.1432-1033.1984.tb08142.x| doi-access = free }} 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), the precursor to the steroid hormones.

It is an agonist of the liver X receptor.