2,3-Oxidosqualene

2,3-Oxidosqualene
Names
IUPAC name
2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
Other names
Squalene oxide
2,3-Squalene oxide
Squalene epoxide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH 2,3-oxidosqualene
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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Infobox references

(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 2,3-(R)-oxidosqualene is an inhibitor of lanosterol synthase.

References

  1. ↑ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports. 24 (6): 1311–31. PMID 18033581. doi:10.1039/b616857b.
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