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Tyrosol

From Wikipedia, the free encyclopedia
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 InfoCard100.007.210Edit 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 mass138.164 g/mol
Melting point91 to 92 °C (196 to 198 °F; 364 to 365 K)
Boiling point158 °C (316 °F; 431 K) at 4 Torr
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Tyrosol is anorganic compound with the formulaHOC6H4CH2CH2OH. Classified as aphenylethanoid, a derivative ofphenethyl alcohol, it is found in a variety of natural sources. The compound is colorless solid. The principal source in the human diet isolive oil.[1][2]

Research

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

Tyrosol may also be cardioprotective. Tyrosol-treated animals showed significant increase in the phosphorylation ofAkt,eNOS, andFOXO3a.[5] In addition, tyrosol also induced the expression of the proteinSIRT1 in the heart aftermyocardial infarction (MI) in a rat MI model.[6]

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

See also

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References

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  1. ^Charoenprasert, Suthawan; Mitchell, Alyson (2012). "Factors Influencing Phenolic Compounds in Table Olives (Olea europaea)".Journal of Agricultural and Food Chemistry.60 (29):7081–7095.doi:10.1021/jf3017699.PMID 22720792.
  2. ^Karković Marković, Ana; Torić, Jelena; Barbarić, Monika; Jakobušić Brala, Cvijeta (2019)."Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health".Molecules.24 (10): 2001.doi:10.3390/molecules24102001.PMC 6571782.PMID 31137753.
  3. ^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.
  4. ^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.
  5. ^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.
  6. ^Samuel, Samson Mathews; Thirunavukkarasu, Mahesh; Penumathsa, Suresh Varma; Paul, Debayon; Maulik, Nilanjana (2008-10-22)."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):9692–9698.doi:10.1021/jf802050h.ISSN 1520-5118.PMC 2648870.PMID 18826227.
  7. ^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.
Food antioxidants
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