Hydroxytyrosol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Hydroxytyrosol
Hydroxytyrosol
Identifiers
CAS number 10597-60-1 YesY
PubChem 82755
ChemSpider 74680 YesY
ChEBI CHEBI:68889 N
ChEMBL CHEMBL485747 N
Jmol-3D images Image 1
Properties
Molecular formula C8H10O3
Molar mass 154.16 g/mol
Appearance Clear, colorless liquid
Solubility in water 5 g/100 ml (25 °C)
Hazards
MSDS External MSDS
Main hazards Irritant, flammable
Flash point 15 °C (59 °F; 288 K)
Related compounds
Related alcohols ethanol, phenol, tyrosol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties. After gallic acid, hydroxytyrosol is believed to be one of the most powerful antioxidants. Its oxygen radical absorbance capacity is 40,000 umolTE/g, which is ten times higher than that of green tea, and two times higher than that of CoQ10.[citation needed]

In nature, hydroxytyrosol is found in olive leaf which is used for medical purposes, with immunostimulant and antibiotic properties.[2] It also exists in olive oil, in the form of its elenolic acid ester oleuropein and, especially after degradation, in its plain form. Oleuropein, along with oleocanthal, are responsible for the bitter taste of extra virgin olive oil. Hydroxytyrosol itself in pure form is a colorless, odourless liquid. The olives, leaves and olive pulp contain large amounts of hydroxytyrosol (compared to olive oil), most of which can be recovered to produce hydroxytyrosol extracts. However, it was found that black olives, such as common canned variety, containing Iron(II) gluconate contained very little of the original hydroxytyrosol as iron salts are catalysts for its oxidation.[3]

Hydroxytyrosol is also a metabolite of the neurotransmitter dopamine.

Research into potential health effects[edit]

In vitro studies[edit]

An olive oil fraction containing DHPE can inhibit platelet aggregation and eicosanoid (thromboxane B2) formation in vitro.[4]

In vivo studies[edit]

Studies have shown that a low dose of hydroxytyrosol reduces the consequences of sidestream smoke-induced oxidative stress in rats.[5]

Ex vivo data provide the first evidence of neuroprotective effects of oral hydroxytyrosol intake. Both, ex vivo and in vitro studies identified mitochondria as one target for hydroxytyrosol's preventive effects in the brain.[6][7]

Metabolism[edit]

In the brain, it degrades to homovanillyl alcohol, via COMT.

See also[edit]

References[edit]

  1. ^ Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil. M. Baldioli, M. Servili, G. Perretti and G. F. Montedoro, Journal Of The American Oil Chemists' Society, 1996 Number 11, Volume 73, pages 1589-1593,{{doi[10.1007/BF02523530}}
  2. ^ Pinelli et al. Quali-quantitative analysis and antioxidant activity of different polyphenolic extracts from Olea europea L. leaves, 2000.
  3. ^ http://www.sciencedirect.com/science/article/pii/S0308814600003381
  4. ^ Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Anna Petroni, Milena Blasevich, Marco Salami, Nadia Papini, Gian F. Montedoro and Claudio Gallia, Thrombosis Research, 15 April 1995, Volume 78, Issue 2, Pages 151–160, doi:10.1016/0049-3848(95)00043-7
  5. ^ Visioli F, Galli C, Plasmati E, et al. (2000). "Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress". Circulation 102 (18): 2169–71. PMID 11056087. 
  6. ^ Schaffer S, Podstawa M, Visioli F, et al. (2007). "Hydroxytyrosol-rich olive wastewater extract protects brain cells in vitro and ex vivo". Journal of Agricultural and Food Chemistry 55 (13): 5043–5049. doi:10.1021/jf0703710. 
  7. ^ Schaffer S, Müller WE, Eckert GP (2010). "Cytoprotective effects of olive wastewater extract and its main constitute hydroxytyrosol in PC12 cells". Pharmacol. Res. 62 (4): 322–327. doi:10.1016/j.phrs.2010.06.004. PMID 20600919.