oleocanthal

Oleocanthal is a naturally occurring phenolic compound, specifically a phenylethanoid and a monophenolic secoiridoid, found exclusively in extra virgin olive oil[1][2][3][4][9]. Its chemical structure is 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid, and it is a tyrosol ester related to oleuropein[8][9]. Oleocanthal is responsible for the characteristic pungency (“throat burn”) in high-quality olive oils[4][5][7]. The principal mechanism of action is its non-selective inhibition of cyclooxygenase-1 and cyclooxygenase-2 (COX-1, COX-2), similar to ibuprofen but with greater potency on a molar basis[1][3][5][7][9]. It also disrupts multiple signaling pathways in cancer and inflammatory processes, including inhibition of mTOR, STAT3, Akt, MAPK, and B-Raf, and suppresses the inflammasome cascade[1]. Oleocanthal has shown anti-cancer, anti-inflammatory, antioxidant, neuroprotective, antimicrobial, anti-fibrotic, and potential anti-Alzheimer’s effects in vitro and in vivo[1][3][4][5][7][9]. Its health impacts are being actively researched as a nutraceutical and for possible use as a supportive agent in cancer therapy and chronic inflammatory diseases[1][4][5][6][7].

Other names

2-(4-hydroxyphenyl)ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate(-)-oleocanthal