Oleocanthal
Title: Oleocanthal
CAS Registry Number: 289030-99-5
CAS Name: (3S,4E)-4-Formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester
Additional Names: deacetoxy ligstroside aglycon
Molecular Formula: C17H20O5
Molecular Weight: 304.34
Percent Composition: C 67.09%, H 6.62%, O 26.29%
Literature 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).
Properties: [a]D25 -0.78° (c = 0.9 in chloroform). uv max (chloroform): 242, 277, 283 sh, 325 nm.
Optical Rotation: [a]D25 -0.78° (c = 0.9 in chloroform)
Absorption maximum: uv max (chloroform): 242, 277, 283 sh, 325 nm

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