“20α,22R-Dihydroxycholesterol”的意思、由来-开放百科全书

词条

20α,22R-Dihydroxycholesterol

释义

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References

{{DISPLAYTITLE:20α,22R-Dihydroxycholesterol}}{{Chembox
| ImageFile = 20a,22R-Dihydroxycholesterol.svg
| ImageSize = 200px
| IUPACName = (3β)-Cholest-5-ene-3,20,22-triol
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo =
| PubChem = 6453841
| ChemSpiderID = 4956189
| SMILES = CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O)O
| StdInChI = 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
| StdInChIKey = ISBSSBGEYIBVTO-TYKWNDPBSA-N
|Section2={{Chembox Properties
| Formula = C₂₇H₄₆O₃
| MolarMass = 418.652 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

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.

References

1. ^¹{{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 | issue = | pages = 703–4 |date=March 1962 | pmid = 13878470 | doi = | url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13878470}}
2. ^¹{{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 / FEBS | volume = 140 | issue = 3 | pages = 583–91 |date=May 1984 | pmid = 6723652 | doi = 10.1111/j.1432-1033.1984.tb08142.x| url = http://onlinelibrary.wiley.com/resolve/openurl?genre=article&issn=0014-2956&date=1984&volume=140&issue=3&spage=583}}

{{Cholesterol and steroid intermediates}}{{Steroid hormones}}{{DEFAULTSORT:Dihydroxycholesterol, 20alpha, 22R-}}{{metabolism-stub}}{{steroid-stub}}

2 : Cholestanes|Sterols

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References