2,3-Oxidosqualene
Names | |
---|---|
Preferred IUPAC name 2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane | |
Other names Squalene oxide 2,3-Squalene oxide Squalene epoxide Squalene-2,3-epoxide | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChEBI |
|
ChemSpider |
|
MeSH | 2,3-oxidosqualene |
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C30H50O |
Molar mass | 426.717 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Chemical compound
(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.[1]
The stereoisomer (R)-2,3-oxidosqualene is an inhibitor of lanosterol synthase.
References
- ^ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Product Reports. 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.
External links
- Oxidosqualene cyclase, PDB December 2007 Molecule of the Month
- v
- t
- e
to HMG-CoA | |
---|---|
Ketone bodies | |
to DMAPP | |
Geranyl- | |
Carotenoid |
- Farnesyl pyrophosphate
- Squalene
- 2,3-Oxidosqualene
- Lanosterol
- Lanosterol
- 14-demethyllanosterol
- 4alpha-Methylzymosterol
- Zymosterone
- Zymosterol
- Zymosterol
- Zymostenol
- Lathosterol
- 7-Dehydrocholesterol
- Cholesterol
- Zymosterol
- Cholesta-7,24-dien-3-ol
- 7-Dehydrodesmosterol
- Desmosterol
- Cholesterol
to Steroid hormones
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- See here instead.
To Sitosterol |
|
---|---|
To Ergocalciferol |
|