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Oleocanthal

Oleocanthal

Chemical name	(3S,4E)-2-(4-hydroxyphenyl)ethyl 4-formyl-3-(2-oxoethyl)-hex-4-enoate
Chemical formula	C₁₇H₂₀O₅
Molecular mass	304.34 g/mol
CAS number	[289030-99-5]
Density	? g/cm³
SMILES	OC1=CC=C(CCOC(C[C@H] (CC=O)/C(C=O)=C\C)=O)C=C1
Disclaimer and references

Oleocanthal is a natural organic compound isolated from extra virgin olive oil. It is responsible for the slightly peppery "bite" of extra virgin olive oil. Oleocanthal is an tyrosol ester and its chemical structure is related to oleuropein that is also found in olive oil.

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Oleocanthal has been found to be have anti-inflammatory and antioxidant properties. Similar to classical NSAIDs, it is a non-selective inhibitor of cyclooxygenase (COX). It is suggested that long-term consumption of small quantities of oleocanthal from olive oil may be responsible in part for the low incidence of heart disease associated with a Mediterranean diet.

References

"Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil." Beauchamp, Gary K.; Keast, Russell S. J.; Morel, Diane; Lin, Jianming; Pika, Jana; Han, Qiang; Lee, Chi-Ho; Smith, Amos B.; Breslin, Paul A. S. Nature (2005), 437(7055), 45-46.
"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." Smith, Amos B., III; Han, Qiang; Breslin, Paul A. S.; Beauchamp, Gary K. Organic Letters (2005), 7(22), 5075-5078.