6829. Oleocanthal
Nomenclature
CAS number: 289030-99-5
(3S,4E)-4-Formyl-3-(2-oxoethyl)-4-hexenoic
acid 2-(4-hydroxyphenyl)ethyl ester; deacetoxy ligstroside aglycon. C17H20O5; mol wt 304.34.
C 67.09%, H 6.62%, O 26.29%.
Description and references
Secoiridoid found in virgin olive oil; induces a characteristic burning sensation in the throat when tasted. Isoln and proposed formation from ligstroside: G. Montedoro et al., J. Agric. Food Chem. 41, 2228 (1993). Antioxidant activity: R. W. Owen et al., Food Chem. Toxicol. 38, 647 (2000). Identification as key contributor to pungency of olive oil: P. Andrewes et al., J. Agric. Food Chem. 51, 1415 (2003). Inhibitory effect on cyclooxygenase: G. K. Beauchamp et al., Nature 437, 45 (2005). Synthesis and abs config: A. B. Smith, III et al., Org. Lett. 7, 5075 (2005).
