41719

(3S)-2,3-Oxidosqualene

≥97.5% (HPLC)

• Synonym(s): (S)-2,3-Epoxy-2,3-dihydrosqualene, (S)-22,23-Epoxy-2,6,10,15,19,23-hexamethyl-2,6,10,14,18-tetracosapentaene, (S)-Squalene 2,3-epoxide, (S)-Squalene 2,3-oxide
• Empirical Formula (Hill Notation): C₃₀H₅₀O
• CAS Number: 54910-48-4
• Molecular Weight: 426.72
• MDL number: MFCD28100799
• UNSPSC Code: 12352204
• PubChem Substance ID: 329756144
• NACRES: NA.28

Properties

• Assay: ≥97.5% (HPLC)
• form: liquid
• optical purity: enantiomeric excess: ≥90.0%
• suitability: conforms to structure for Proton NMR spectrum
• storage temp.: −20°C
• SMILES string: CC1(C)O[C@H]1CC/C(C)=C/CC/C(C)=C/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C
• 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+/t29-/m0/s1
• InChI key: QYIMSPSDBYKPPY-RSKUXYSASA-N

Description

Application

• Schizophrenic behavior of 2,3-Oxidosqualene Sterol Cyclase from pig liver towards 2,3-oxidosqualene analogues. Alain Krief and colleagues discuss the variable catalytic behaviors of oxidosqualene cyclase when interacting with different oxidosqualene analogues, suggesting implications for sterol production efficiency and specificity (Krief et al., 2021).

Biochem/physiol Actions

(S)-2,3-Epoxysqualene is an intermediate of many metabolic pathways such as the steroid biosynthesis, sesquiterpenoid and triterpenoid biosynthesis, biosynthesis of plant secondary metabolites, biosynthesis of terpenoids and steroids, biosynthesis of plant hormones, biosynthesis of secondary metabolites, and biosynthesis of antibiotics.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable