Oleocanthal

Structural formula
General
Surname	Oleocanthal
other names	2- (4-hydroxyphenyl) ethyl- (3 S , 4 E ) -4-formyl-3- (2-oxoethyl) -4-hexenoate ( IUPAC )
Molecular formula	C 17 H 20 O 5
External identifiers / databases
CAS number 289030-99-5 PubChem 11652416 ChemSpider 9827154 Wikidata Q402613
properties
Molar mass	304.34 g · mol -1
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oleocanthal (oleo - oil, canth - stitch, al - aldehyde) describes an active ingredient that was first discovered in olive oil . Chemically it is an aromatic ester with two aldehyde groups . In the laboratory it has anti-inflammatory and antioxidant effects .

Biological effects

In September 2005, the scientist Gary K. Beauchamp, employee of the Monell Institute , published his discovery for the first time that a substance in extra virgin olive oil has anti-inflammatory, i.e. anti-inflammatory effects. A stinging stimulus in the throat when he took olive oil caught his attention, which he had noticed before when he was given ibuprofen orally.

Studies have shown that just like ibuprofen or acetylsalicylic acid, for example, the newly discovered oleocanthal inhibits the enzyme cyclooxygenase (COX). There are two different types of enzymes, COX-1 and COX-2, which have different tasks such as platelet aggregation or inflammation mediation. Both enzymes are, as also z. B. by acetylsalicylic acid , or agents from the group of NSAIDs (non-steroidal anti-inflammatory drugs) competitively inhibited, which results in the anti-inflammatory effect.

Since the concentration of oleocanthal in olive oil is quite low, occasional consumption should not have any negative effects (50 g of virgin olive oil per day corresponds to 9 mg of oleocanthal). This dose is 10% of the recommended adult dose for pain when compared to ibuprofen. It is also known that acetylsalicylic acid - another COX inhibitor - when taken regularly, has a preventive effect against cardiovascular diseases. The effects of ibuprofen have been linked to the prevention of platelet aggregation in the blood.

Experiments at the University of Louisiana with laboratory mice lead to the conclusion that the oleocanthal contained in "extra virgin" olive oil could reduce the risk of Alzheimer's disease .

In vitro, oleocanthal caused cancer cell death.

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ↑ 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 from 5075 to 5078. doi : 10.1021 / ol052106a
3. ↑ Gary K. Beauchamp, Russell SJ Keast et al. a .: Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil. In: Nature. 437, 2005, p. 45, doi : 10.1038 / 437045a .
4. ↑ 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
5. ↑ LeGendre O, Breslin PAS, Foster DA: Oleocanthal rapidly and selectively induces cancer cell death via lysosomal membrane permeabilization (LMP). In: Molecular & Cellular Oncology. 2, 2015, p. E1006077, doi : 10.1080 / 23723556.2015.1006077 .