olean12en28oic

Olean12en28oic, or olean-12-en-28-oic acid, is a pentacyclic triterpenoid that forms part of the oleanane family. It is defined by a fused five-ring skeleton (the oleanane framework), a double bond at the 12 position, and a terminal carboxylic acid at carbon 28. The compound serves as a core aglycone for many plant-derived triterpenoids.

Structure and chemistry: The molecule exhibits the classic oleanane pentacyclic backbone with limited oxygen functionality beyond the carboxyl group. The 12-en double bond influences ring conformation and reactivity. As a mono-carboxylic acid, it displays acidic properties and tends to form salts and esters in biochemical contexts.

Biosynthesis and natural occurrence: In plants, olean12en28oic is produced via the mevalonate pathway leading to squalene, conversion to 2,3-oxidosqualene, and cyclization to the oleanane skeleton by oxidosqualene cyclases, followed by oxidation and tailoring. The same skeleton appears in numerous saponins and aglycones across many species, including members of various plant groups.

Applications and significance: The oleanane skeleton is widely used in natural product chemistry and pharmacology. Olean12en28oic serves as a reference structure for synthesizing related triterpenoids; derivatives have been explored for anti-inflammatory, anti-cancer, and antimicrobial activities, though specific activity depends on functionalization at the 3, 28, and other positions.

Related compounds include the oleanane family, oleanolic acid, and β-amyrin.