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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.210 Edit this at Wikidata
UNII
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 checkY
    Key: YCCILVSKPBXVIP-UHFFFAOYSA-N checkY
  • 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,5-6H2
    Key: YCCILVSKPBXVIP-UHFFFAOYSA-N
  • Oc1ccc(cc1)CCO
Properties
C8H10O2
Molar mass 138.164 g/mol
Melting point 91 to 92 °C (196 to 198 °F; 364 to 365 K)
Boiling point 158 °C (316 °F; 431 K) at 4 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Tyrosol is a phenylethanoid, a derivative of phenethyl alcohol. It is a natural phenolic antioxidant present in a variety of natural sources. The principal source in the human diet is olive oil. It is also one of the main natural phenols in argan oil.[citation needed] In olive oil, tyrosol forms esters with fatty acids.[1]

Research

As an antioxidant, tyrosol can protect cells against injury due to oxidation in vitro.[2] 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.[3]

Tyrosol may also be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a.[4] In addition, tyrosol also induced the expression of the protein SIRT1 in the heart after myocardial infarction in a rat MI model.[citation needed]

See also

References

  1. ^ Lucas, Ricardo; Comelles, Francisco; AlcáNtara, David; Maldonado, Olivia S.; Curcuroze, Melanie; Parra, Jose L.; Morales, Juan C. (2010). "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". Journal of Agricultural and Food Chemistry. 58 (13): 8021–8026. doi:10.1021/jf1009928. PMID 20524658.
  2. ^ 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. doi:10.1093/jn/129.7.1269. PMID 10395586.
  3. ^ 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.
  4. ^ 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". Journal of Agricultural and Food Chemistry. 56 (20): 9692–8. doi:10.1021/jf802050h. PMC 2648870. PMID 18826227.