Structure via PubChem · Public domain (PubChem)
squalene oxide
Sign in to saveAlso known as 2,3-Oxidosqualene, Squalene-2,3-oxide, 2,3-Edsq, 2,3-Epoxy-2,3-dihydrosqualene, Squalene-2,3-epoxide, squalene epoxide
'(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.
Chemical data
- Formula
- C30H50O
- Molecular weight
- 426.7 g/mol
- IUPAC name
- 2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaenyl]oxirane
- SMILES
- CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
- InChIKey
- QYIMSPSDBYKPPY-BANQPHDMSA-N
- XLogP
- 10.3
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 426.386166
Show 4 more facts
- chemical formula
- C₃₀H₅₀O
- canonical SMILES
- CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC1C(O1)(C)C)C)C)C
- isomeric SMILES
- CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
- Commons category
- Squalene epoxide
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
'(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.
The stereoisomer (R)-2,3-oxidosqualene is an inhibitor of lanosterol synthase.
Excerpted from Wikipedia’s “squalene oxide” article, available under the CC BY-SA 4.0 licence.