2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane

• ChemBase ID: 125214
• Molecular Formular: C30H50O
• Molecular Mass: 426.7174
• Monoisotopic Mass: 426.38616622
• SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
• Canonical SMILES: C/C(=C\CC/C=C(/CC/C=C(/CCC1OC1(C)C)\C)\C)/CC/C=C(/CCC=C(C)C)\C
• 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+
• InChIKey: QYIMSPSDBYKPPY-BANQPHDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane; 2,2-dimethyl-3-(3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl)oxirane
• IUPAC Traditional name: 2,3-oxidosqualene; 2,2-dimethyl-3-(3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl)oxirane
• Synonyms: Squalene oxide; 2,3-Squalene oxide; 2,3-Oxidosqualene; 2,3-Epoxy-2,3-dihydrosqualene; 22,23-Epoxy-2,6,10,15,19,23-hexamethyl-2,6,10,14,18-tetracosapentaene; Squalene 2,3-epoxide; Squalene 2,3-oxide; 2,3-Oxidosqualene

Database IDs

• CAS Number: 7200-26-2
• MDL Number: MFCD00871184
• PubChem SID: 162219564
• PubChem CID: 5366020
• Chemspider ID: 4517951
• MeSH Name: 2,3-oxidosqualene
• Wikipedia Title: 2,3-Oxidosqualene

CALCULATED PROPERTIES

• Polarizability: 54.892815 Å^3
• Polar Surface Area: 12.53 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 9.443276
• LogD (pH = 7.4): 9.443276
• Log P: 9.443276
• Molar Refractivity: 143.4553 cm^3

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥92.0% (HPLC)

DETAILS

Sigma Aldrich - 41043

Biochem/physiol Actions
2,3-Oxidosqualene is a substrate of the 2,3-oxidosqualene cyclase lanosterol synthase. 2,3-oxidosqualene cyclase has been shown to be suppressed by a high fat diet and high levels of cholesterol. 1