Oleocanthal
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| Names | |
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IUPAC names
2-(4-hydroxyphenyl)ethyl (3S,4E)
-4-formyl-3-(2-oxoethyl)hex-4-enoate |
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| Identifiers | |
289030-99-5 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:85673 
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| ChemSpider |
9827154
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| 6308 | |
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| Properties | |
| C17H20O5 | |
| Molar mass | 304.34 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is ?) |
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| Infobox references | |
Oleocanthal is a phenylethanoid, a type of natural phenolic compound found in extra-virgin olive oil. It appears to be responsible for the burning sensation that occurs in the back of the throat when consuming such oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil.
Oleocanthal has been found to have anti-inflammatory and antioxidant properties in vitro. Similar to classical non-steroidal anti-inflammatory drugs, it is a non-selective inhibitor of cyclooxygenase (COX). 50 g (more than three and a half tablespoons) of a typical extra virgin olive oil per day contains an amount of oleocanthal with similar in vitro anti-inflammatory effect as 1/10 of the adult ibuprofen dose. It is therefore suggested that long-term consumption of small quantities may be responsible in part for the low incidence of heart disease and Alzheimer's disease associated with a Mediterranean diet. However, 50 g is a great deal of olive oil for most consumers; moreover, the absorption, metabolism, and distribution of oleocanthal is not well-characterized, and it is not known whether these in vitro effects actually occur in the body. "Against this background, the in vivo anti-inflammatory effects of dietary oleocanthal cannot be as relevant as hypothesized by Beauchamp et al."
Oleocanthal is an activator of the TRPA1 ion channel, which is activated by ibuprofen. This appears to be responsible for the burning sensation when consuming extra-virgin olive oil.
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