(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]
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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 | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
MeSH | 2,3-oxidosqualene |
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UNII | |
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).
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The stereoisomer (R)-2,3-oxidosqualene is an inhibitor of lanosterol synthase.
References
External links
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