2,3-Oxidosqualene
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(Redirected from 2,3-oxidosqualene)
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Names | |
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IUPAC name
2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
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Other names
Squalene oxide
2,3-Squalene oxide Squalene epoxide |
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Identifiers | |
7200-26-2 ![]() |
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3D model (Jmol) | Interactive image Interactive image |
ChEBI | CHEBI:78662 ![]() |
ChemSpider | 4517951 ![]() |
MeSH | 2,3-oxidosqualene |
PubChem | 5366020 |
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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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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[edit]
- ^ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports. 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.