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
CAS Number	7200-26-2
ChEBI	CHEBI:78662
ChemSpider	4517951
Jmol interactive 3D	Image Image
MeSH	2,3-oxidosqualene
PubChem	5366020
InChI InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+ Key: QYIMSPSDBYKPPY-BANQPHDMSA-N InChI=1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+ Key: QYIMSPSDBYKPPY-BANQPHDMBU
SMILES O1C(C)(C)C1CC/C(=C/CC/C(=C/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C)C CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
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).
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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. doi:10.1039/b616857b. PMID 18033581.

External links

• Oxidosqualene cyclase, PDB December 2007 Molecule of the Month