Tyrosol

Chemical compound From Wikipedia, the free encyclopedia

Tyrosol is an organic compound with the formula HOC6H4CH2CH2OH. Classified as a phenylethanoid, a derivative of phenethyl alcohol, it is found in a variety of natural sources. The compound is colorless solid. The principal source in the human diet is olive oil.[1][2]

Quick facts Names, Identifiers ...
Tyrosol
Names
Preferred 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).
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Research

As an antioxidant, tyrosol may protect cells against injury due to oxidation in vitro.[3] Although it is not as potent as other antioxidants present in olive oil (e.g., hydroxytyrosol), its higher concentration and good bioavailability indicate that it may have an important overall effect.[4]

Tyrosol may also be cardioprotective. Tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS, and FOXO3a.[5] In addition, tyrosol also induced the expression of the protein SIRT1 in the heart after myocardial infarction (MI) in a rat MI model.[6]

Tyrosol forms esters with a variety of organic acids.[7] For example, oleocanthal is the elenolic acid ester of tyrosol.

See also

References

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