2,3-Oxidosqualene
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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 | |
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3D model (JSmol) | |
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ChemSpider | |
MeSH | 2,3-oxidosqualene |
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CompTox Dashboard (EPA) | |
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Properties | |
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). |
(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
[edit]- ^ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Product Reports. 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.