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Tyrosol

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Tyrosol
Names
IUPAC name 4-(2-Hydroxyethyl)phenol
Other names p-Hydroxyphenethyl alcohol
2-(4-Hydroxyphenyl)ethanol
4-Hydroxyphenylethanol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.210 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2Key: YCCILVSKPBXVIP-UHFFFAOYSA-N
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2Key: YCCILVSKPBXVIP-UHFFFAOYSA-N
SMILES
  • Oc1ccc(cc1)CCO
Properties
Chemical formula C8H10O2
Molar mass 138.164 g/mol
Melting point 91–92 °C
Boiling point 158 °C at 4 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Tyrosol is a natural phenolic antioxidant present in a variety of natural sources. The principal source in the human diet is olive oil. Tyrosol is a derivative of phenethyl alcohol

As an antioxidant, tyrosol can protect cells against injury due to oxidation. Although it is not as potent as other antioxidants present in olive oil, its higher concentration and good bioavailability indicate that it may have an important overall effect. This effect may contribute significantly to the health benefits of olive oil and, more generally, the Mediterranean diet.

Recently Tyrosol present in white wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosol's SIRT1, Akt and eNOS activating power adds another dimension to the white wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart.

In olive oil, tyrosol forms esters with fatty acids.

See also

References

  1. Giovannini C, Straface E, Modesti D, Coni E, Cantafora A, De Vincenzi M, Malorni W, Masella R (1999). "Tyrosol, the major olive oil biophenol, protects against oxidized-LDL-induced injury in Caco-2 cells". J. Nutr. 129 (7): 1269–1277. PMID 10395586.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Miró-Casas E, Covas M, Fitó M, Farré-Albadalejo M, Marrugat J, de la Torre R (2003). "Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans". European journal of clinical nutrition. 57 (1): 186–190. doi:10.1038/sj.ejcn.1601532. PMID 12548315.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Samuel SM, Thirunavukkarasu M, Penumathsa SV, Paul D, Maulik N (2008.). "Akt/FOXO3a/SIRT1-Mediated Cardioprotection by n-Tyrosol against Ischemic Stress in Rat in Vivo Model of Myocardial Infarction: Switching Gears toward Survival and Longevity". J.Agric. Food. Chem. 56 (20): 9692–8. doi:10.1021/jf802050h. PMC 2648870. PMID 18826227. {{cite journal}}: Check date values in: |year= (help)CS1 maint: multiple names: authors list (link) CS1 maint: year (link)
  4. Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters: A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions. Ricardo Lucas, Francisco Comelles, David Alcntara, Olivia S. Maldonado, Melanie Curcuroze, Jose L. Parra and Juan C. Morales, J. Agric. Food Chem., 2010, 58 (13), pp 8021–8026, doi:10.1021/jf1009928
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