2,3-Oxidosqualene - Misplaced Pages

This is an old revision of this page, as edited by Sheac (talk | contribs) at 04:53, 17 May 2011. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

2,3-Oxidosqualene
Names

IUPAC name 2,2-Dimethyl-3-oxirane
Other names Squalene oxide 2,3-Squalene oxide
Identifiers
CAS Number	7200-26-2
3D model (JSmol)	Interactive image Interactive image
ChemSpider	4517951
MeSH	2,3-oxidosqualene
PubChem CID	5366020
CompTox Dashboard (EPA)	DTXSID50900960
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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

2,3-(S) Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed from squalene by squalene monooxygenase. 2,3 oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.

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

References

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

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

This biochemistry article is a stub. You can help Misplaced Pages by expanding it.