Oleocanthal is a phenyl ethanoid, a natural phenolic compound found in extra virgin olive oil. It appears to be responsible for the burning sensation that occurs at the back of the throat when such oil is consumed. Oleocanthal is an ester of tyrosol and its chemical structure is related to oleuropein, which is also found in olive oil.[1][2][3]

Oleocanthal is one of the most important and well-studied constituents among the olive oil phenolic fraction. Its presence in olive oil was firstly mentioned by researcher Montedoro in 1993* and it appears in varying levels in olive oil. According to extended and well documented studies oleocanthal’s concentration may reach 2273 mg/Kg in olive oil and the concentration is affected by different genetic and pedoclimatic factors*.

Oleocanthal has been found to have anti-inflammatory and antioxidant properties in vitro. Similar to the classic non-steroidal anti-inflammatory drugs, it is a non-selective cyclooxygenase (COX) inhibitor. 50 g of a typical extra virgin olive oil per day contains an amount of oleocanthal with similar in vitro anti-inflammatory activity to 1/10 of an adult dose of ibuprofen. [4] Therefore, it is suggested that long-term consumption of small amounts may contribute to the low incidence of heart disease and Alzheimer's disease associated with the Mediterranean diet.[5][6]

However, 50 grams is too much olive oil for most consumers. Furthermore, the absorption, metabolism and distribution of oleocanthal are not well characterized and it is not known whether these in vitro effects actually occur in the body.[7]

Recently, oleocanthal has been shown to have potential as a therapeutic agent in the treatment of inflammatory degenerative joint diseases.8 Oleocanthal inhibits LPS-induced NO production in J774 macrophages without affecting cell viability. In addition, it inhibits MIP-1α and IL-6 mRNA expression, as well as protein synthesis, in both ATDC5 chondrocytes and J774 macrophages. Oleocanthal also inhibits protein synthesis of IL-1β, TNF-α and GM-CSF by LPS-stimulated macrophages.9

The biological activities of oleocanthal started studying many years later by Beauchamp in 2006* in research which the anti-inflammatory activity was highlighted and also revealed that oleocanthal is the constituent that gives olive oil the pungent taste.


1. Amos B. Smith, III et al.: Synthesis and Assignment of Absolute Configuration of (−)-Oleocanthal: A Potent, Naturally Occurring Non-steroidal Anti-inflammatory and Anti-oxidant Agent Derived from Extra Virgin Olive Oils. In: Org. Lett. 7/22/2005 pp 5075–5078. doi:10.1021/ol052106a
2. Gary K. Beauchamp, Russell S. J. Keast u. a.: Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil. In: Nature. 437, 2005, S. 45, doi:10.1038/437045a.
3. Abuznait, Alaa H. et al.: Olive-Oil-Derived Oleocanthal Enhances β-Amyloid Clearance as a Potential Neuroprotective Mechanism against Alzheimer’s Disease : in Vitro and in Vivo Studies. In: ACS Chem Neurosci. 2013, 4: 973–982. doi:10.1021/cn400024q
4. Beauchamp, G. K.; Keast, R. S.; Morel, D.; Lin, J.; Pika, J.; Han, Q.; Lee, C. H.; Smith, A. B. και άλλοι. (31 August 2005). «Extra-virgin olive oil mimics painkiller». Nature (Nature Publishing Group) 437 (7055): 45–6. doi:10.1038/437045a. PMID 16136122.
5. Beauchamp GK; Keast RS; Morel D και άλλοι. (September 2005). «Phytochemistry: ibuprofen-like activity in extra-virgin olive oil». Nature 437 (7055): 45–6. doi:10.1038/437045a. PMID 16136122. Bibcode: 2005Natur.437...45B.
6. Abuznait, AH; Qosa, H; Busnena, BA; El Sayed, KA; Kaddoumi, A (February 25, 2013). «Olive-Oil-Derived Oleocanthal Enhances β-Amyloid Clearance as a Potential Neuroprotective Mechanism against Alzheimer's Disease: In Vitro and in Vivo Studies.». ACS Chemical Neuroscience 4 (6): 973–82. doi:10.1021/cn400024q. PMID 23414128.
7. Fogliano, Vincenzo; Raffaele Sacchi (January 2006). «Oleocanthal in olive oil: Between myth and reality». Molecular Nutrition & Food Research 50 (1): 5–6. doi:10.1002/mnfr.200690002. PMID 16397870.
8. Iacono, A; Gómez, R; Sperry, J; Conde, J; Bianco, G; Meli, R; Gómez-Reino, JJ; Smith Ab, 3rd και άλλοι. (2010). «Effect of oleocanthal and its derivatives on inflammatory response induced by lipopolysaccharide in a murine chondrocyte cell line». Arthritis and Rheumatism 62 (6): 1675–82. doi:10.1002/art.27437. PMID 20201078.
9. Scotece, Morena; Gómez, Rodolfo; Conde, Javier; Lopez, Verónica; Gómez-Reino, Juan J.; Lago, Francisca; Smith, Amos B.; Gualillo, Oreste (2012). «Further evidence for the anti-inflammatory activity of oleocanthal: Inhibition of MIP-1α and IL-6 in J774 macrophages and in ATDC5 chondrocytes». Life Sciences 91 (23–24): 1229–35. doi:10.1016/j.lfs.2012.09.012. PMID 23044226.