3hydroxyolean12en28oic

3-hydroxyolean12en28oic, commonly known as oleanolic acid, is a natural pentacyclic triterpenoid. Its systematic name is 3β-hydroxy-olean-12-en-28-oic acid. The structure features the oleanane skeleton with a hydroxyl group at carbon 3, a double bond between carbons 12 and 13, and a carboxylic acid at carbon 28. Its molecular formula is C30H48O3 and its molecular weight is roughly 456.7 g/mol.

Oleanolic acid is widely distributed in the plant kingdom, notably in olives and olive leaves, apples, and many herbs. It frequently occurs as the free acid or as glycosides and esters within plant triterpenoid saponins. The compound is often encountered as part of complex natural mixtures rather than in isolation in nature.

In pharmacology and biomedicine, oleanolic acid has been investigated for hepatoprotective, anti-inflammatory, antimicrobial, and anticancer activities in vitro and in animal models. While these studies indicate potential biological effects, clinical evidence is limited and the compound is not approved as a therapeutic drug. It is commonly regarded as a contributing component of the biological activity of various plant extracts rather than a standalone medicine.

Applications and research use include serving as a reference standard for triterpenoids and as a precursor for the semi-synthesis of other oleanane-type compounds used in cosmetics and nutraceuticals. Biosynthetically, oleanolic acid is produced in plants via the mevalonate pathway, with cyclization to the oleanane skeleton followed by oxidative modifications.