Hydroxytyrosol

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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 154.163193 g/mol
Appearance Clear, faint yellow to yellow liquid
Boiling point 174 °C
Solubility in water 5 g/100 ml (25 °C)
Hazards
MSDS [1]
R-phrases R36/37/38
S-phrases S26, S37/39
Main hazards Causes skin irritation.

Causes serious eye irritation.

May cause respiratory irritation.

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 in vitro. In nature, hydroxytyrosol is found in olive leaf and 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, odorless 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.[2]

Hydroxytyrosol is also a metabolite of the neurotransmitter dopamine.[citation needed]

Research into potential health effects[edit]

In vitro studies[edit]

An olive oil fraction containing hydroxytyrosol can inhibit platelet aggregation and eicosanoid (thromboxane B2) formation in vitro.[3] In basic research, hydroxytyrosol had evidence for antimicrobial and antibiotic properties.[4][5]

In vivo studies[edit]

Studies have shown that a low dose of hydroxytyrosol reduces the consequences of sidestream smoke-induced oxidative stress in rats.[6]

Ex vivo data provide the first evidence of possible neuroprotective effects of oral hydroxytyrosol intake. Both, ex vivo and in vitro studies identified mitochondria as one target for hydroxytyrosol effects in the brain.[7][8]

Metabolism[edit]

In the brain, hydroxytyrosol is metabolized to homovanillyl alcohol by the enzyme catechol-O-methyl transferase.

See also[edit]

References[edit]

  1. ^ M. Baldioli, M. Servili, G. Perretti and G. F. Montedoro (1996). "Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil". Journal Of The American Oil Chemists' Society 73 (11): 1589–1593. doi:10.1007/BF02523530. 
  2. ^ Vincenzo Marsilio, Cristina Campestre, Barbara Lanza (July 2001). "Phenolic compounds change during California-style ripe olive processing". Food Chemistry 74 (1): 55–60. doi:10.1016/S0308-8146(00)00338-1. 
  3. ^ Petroni, A.; Blasevich, M.; Salami, M.; Papini, N.; Montedoro, G. F.; Galli, C. (1995). "Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil". Thrombosis Research 78 (2): 151–60. doi:10.1016/0049-3848(95)00043-7. PMID 7482432.  edit
  4. ^ Bisignano, G; Tomaino, A; Lo Cascio, R; Crisafi, G; Uccella, N; Saija, A (1999). "On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol". The Journal of pharmacy and pharmacology 51 (8): 971–4. doi:10.1211/0022357991773258. PMID 10504039.  edit
  5. ^ Capasso, R; Evidente, A; Schivo, L; Orru, G; Marcialis, M. A.; Cristinzio, G (1995). "Antibacterial polyphenols from olive oil mill waste waters". The Journal of applied bacteriology 79 (4): 393–8. PMID 7592132.  edit
  6. ^ Visioli F, Galli C, Plasmati E, et al. (2000). "Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress". Circulation 102 (18): 2169–71. doi:10.1161/01.cir.102.18.2169. PMID 11056087. 
  7. ^ 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. 
  8. ^ 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.