2,3-Oxidosqualene  (Synonyms: Squalene oxide)

2,3-Oxidosqualene (Squalene oxide) is a sterol biosynthesis precursor intermediate.2,3-Oxidosqualene participates in cyclization pathways that form sterols and triterpenes, and contributes to introduction of their characteristic 3-hydroxyl group.2,3-Oxidosqualene forms metabolically from squalene in rat liver homogenates under sterol synthesis conditions.2,3-Oxidosqualene converts to sterols including cholesterol, lathosterol, and lanost-8-en-3β-ol in rat liver homogenates under anaerobic conditions^[1].

2,3-oxidosqualene (30 min; aerobic/anaerobic conditions) is synthesized from squalene in rat liver homogenates, and is efficiently converted to sterols (40% overall conversion under aerobic conditions, 80% per single enantiomer) with greater anaerobic conversion efficiency than squalene, confirming it as an intermediate in rat liver sterol biosynthesis^[1].
2,3-oxidosqualene (anaerobic conditions) is converted by rat liver homogenates primarily to lanost-8-en-3β-ol, which can be further converted to cholesterol and cholest-7-en-3β-ol under aerobic conditions^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

426.72

C₃₀H₅₀O

7200-26-2

Oil

Colorless to light yellow

C/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C=C(C)/CC/C=C(C)/CCC1C(C)(O1)C

Shipping with dry ice.

-80°C

• [1]. Cory EJ, et al. 2,3-oxidosqualene, an intermediate in the biological synthesis of sterols from squalene. J Am Chem Soc. 1966 Oct 20;88(20):4750-1.  [Content Brief]