23Oxidosqualene

23oxidosqualene is commonly referred to as 2,3-oxidosqualene, a key biochemical intermediate in sterol biosynthesis. It is the 2,3-epoxide form of squalene produced when squalene is oxidized by squalene epoxidase (squalene monooxygenase) in the presence of NADPH and molecular oxygen. The epoxide structure activates the molecule for the subsequent cyclization step.

In eukaryotes, 2,3-oxidosqualene is the substrate for oxidosqualene cyclase, which catalyzes a complex cyclization to form the core sterol framework. In animals and fungi, this cyclization yields lanosterol, which is further processed to cholesterol or other sterols. In plants, the analogous reaction produces cycloartenol, a precursor to plant sterols. Thus, 2,3-oxidosqualene sits at a central branching point that directs the production of diverse sterols essential for membrane structure and function.

Chemical properties and synonyms: the compound has the molecular formula C30H50O and is often called squalene oxide or 2,3-oxidosqualene. It is a triterpene containing an epoxide ring, formed from the oxidation of the intact hydrocarbon squalene.

Medical and research relevance: inhibitors of squalene epoxidase, such as terbinafine, disrupt the production of downstream sterols and are used as antifungal agents. The intermediate is also studied to understand the regulation of sterol biosynthesis and its impacts on cellular membrane properties.

Overall, 2,3-oxidosqualene is a short-lived but essential precursor in the biosynthetic pathway that generates the sterol backbone across eukaryotes.