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Chemical Compound Review

Tyrosol     4-(2-hydroxyethyl)phenol

Synonyms: PHEP, p-Tyrosol, p-Thyrosol, PubChem9418, CHEMBL53566, ...
 
 
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Disease relevance of Tyrosol

  • For the first time, a soil bacterium, designated Pseudomonas aeruginosa, was isolated based on its ability to grow on tyrosol as a sole source of carbon and energy [1].
  • A reduced toxicity of the UV/RB-irradiated solutions of cathecol and tyrosol towards alga Ankistrodesmus braunii is also verified [2].
  • A soil bacterium, designated Serratia marcescens strain, was isolated on the basis of its ability to grow on p-tyrosol (4-hydroxyphenylethanol) as a sole source of carbon and energy [3].
 

High impact information on Tyrosol

 

Biological context of Tyrosol

 

Anatomical context of Tyrosol

 

Associations of Tyrosol with other chemical compounds

 

Gene context of Tyrosol

  • A red wine fraction rich in polymeric flavanols and a white wine one rich in phenolic acids, flavonols, and tyrosol strongly lowered Hsp27 levels [18].
  • RESULTS: Urinary tyrosol and hydroxytyrosol increased (p < 0.020), in vivo plasma oxidized LDL decreased (p = 0.006), and ex vivo resistance of LDL to oxidation increased (p = 0.012) with the phenolic content of the olive oil administered [19].
  • Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans [20].
  • Effect of Added Caffeic Acid and Tyrosol on the Fatty Acid and Volatile Profiles of Camellia Oil following Heating [21].
  • This o-diphenol (not commercially available) was obtained from its monophenolic precursor tyrosol (commercially available) in the presence of both tyrosinase and ascorbic acid [22].
 

Analytical, diagnostic and therapeutic context of Tyrosol

References

  1. Use of whole cells of Pseudomonas aeruginosa for synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol. Allouche, N., Damak, M., Ellouz, R., Sayadi, S. Appl. Environ. Microbiol. (2004) [Pubmed]
  2. A mild photochemical approach to the degradation of phenols from olive oil mill wastewater. Cermola, F., DellaGreca, M., Iesce, M.R., Montella, S., Pollio, A., Temussi, F. Chemosphere (2004) [Pubmed]
  3. Synthesis of hydroxytyrosol, 2-hydroxyphenylacetic acid, and 3-hydroxyphenylacetic acid by differential conversion of tyrosol isomers using Serratia marcescens strain. Allouche, N., Sayadi, S. J. Agric. Food Chem. (2005) [Pubmed]
  4. Tyrosol is a quorum-sensing molecule in Candida albicans. Chen, H., Fujita, M., Feng, Q., Clardy, J., Fink, G.R. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  5. Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophages RAW 264.7. Moreno, J.J. Free Radic. Biol. Med. (2003) [Pubmed]
  6. Tyrosol bioavailability in humans after ingestion of virgin olive oil. Miró Casas, E., Farré Albadalejo, M., Covas Planells, M.I., Fitó Colomer, M., Lamuela Raventós, R.M., de la Torre Fornell, R. Clin. Chem. (2001) [Pubmed]
  7. The fate of olive oil polyphenols in the gastrointestinal tract: Implications of gastric and colonic microflora-dependent biotransformation. Corona, G., Tzounis, X., Assunta Dessì, M., Deiana, M., Debnam, E.S., Visioli, F., Spencer, J.P. Free Radic. Res. (2006) [Pubmed]
  8. Hydroxytyrosol, a natural molecule occurring in olive oil, induces cytochrome c-dependent apoptosis. Ragione, F.D., Cucciolla, V., Borriello, A., Pietra, V.D., Pontoni, G., Racioppi, L., Manna, C., Galletti, P., Zappia, V. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  9. The fate of olive oil polyphenols in the gastrointestinal tract: implications of gastric and colonic microflora-dependent biotransformation. Corona, G., Tzounis, X., Assunta Dessì, M., Deiana, M., Debnam, E.S., Visioli, F., Spencer, J.P. Free Radic. Res. (2006) [Pubmed]
  10. The effect of tyrosol, hydroxytyrosol and oleuropein on the non-enzymatic lipid peroxidation of rat liver microsomes. Gutierrez, V.R., de la Puerta, R., Catalá, A. Mol. Cell. Biochem. (2001) [Pubmed]
  11. Biological activity of acetylated phenolic compounds. Fragopoulou, E., Nomikos, T., Karantonis, H.C., Apostolakis, C., Pliakis, E., Samiotaki, M., Panayotou, G., Antonopoulou, S. J. Agric. Food Chem. (2007) [Pubmed]
  12. Tyrosol, the major olive oil biophenol, protects against oxidized-LDL-induced injury in Caco-2 cells. Giovannini, C., Straface, E., Modesti, D., Coni, E., Cantafora, A., De Vincenzi, M., Malorni, W., Masella, R. J. Nutr. (1999) [Pubmed]
  13. Production of High Hydroxytyrosol Yields via Tyrosol Conversion by Pseudomonas aeruginosa Immobilized Resting Cells. Bouallagui, Z., Sayadi, S. J. Agric. Food Chem. (2006) [Pubmed]
  14. 4-Hydroxyphenethyl alcohol--a new cytokinin-like substance from the phototrophic purple bacterium Rhodospirillum rubrum 1R. Serdyuk, O.P., Smolygina, L.D., Muzafarov, E.N., Adanin, V.M., Arinbasarov, M.U. FEBS Lett. (1995) [Pubmed]
  15. Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake. Miró-Casas, E., Farré Albaladejo, M., Covas, M.I., Rodriguez, J.O., Menoyo Colomer, E., Lamuela Raventós, R.M., de la Torre, R. Anal. Biochem. (2001) [Pubmed]
  16. Comparison of antioxidant activity between aromatic indolinonic nitroxides and natural and synthetic antioxidants. Damiani, E., Belaid, C., Carloni, P., Greci, L. Free Radic. Res. (2003) [Pubmed]
  17. Development of a sensitive and specific solid phase extraction--gas chromatography-tandem mass spectrometry method for the determination of elenolic acid, hydroxytyrosol, and tyrosol in rat urine. Bazoti, F.N., Gikas, E., Puel, C., Coxam, V., Tsarbopoulos, A. J. Agric. Food Chem. (2005) [Pubmed]
  18. Decrease of heat shock protein levels and cell populations by wine phenolic extracts. Roussou, I., Lambropoulos, I., Pagoulatos, G.N., Fotsis, T., Roussis, I.G. J. Agric. Food Chem. (2004) [Pubmed]
  19. Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation--a randomized controlled trial. Marrugat, J., Covas, M.I., Fitó, M., Schröder, H., Miró-Casas, E., Gimeno, E., López-Sabater, M.C., de la Torre, R., Farré, M. European journal of nutrition. (2004) [Pubmed]
  20. Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Covas, M.I., Miró-Casas, E., Fitó, M., Farré-Albadalejo, M., Gimeno, E., Marrugat, J., De La Torre, R. Drugs under experimental and clinical research. (2003) [Pubmed]
  21. Effect of Added Caffeic Acid and Tyrosol on the Fatty Acid and Volatile Profiles of Camellia Oil following Heating. Haiyan, Z., Jr, D.R., Bishop, A.G., Prenzler, P.D., Robards, K. J. Agric. Food Chem. (2006) [Pubmed]
  22. Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst. Espín, J.C., Soler-Rivas, C., Cantos, E., Tomás-Barberán, F.A., Wichers, H.J. J. Agric. Food Chem. (2001) [Pubmed]
  23. Analysis of minor components in olive oil. Murkovic, M., Lechner, S., Pietzka, A., Bratacos, M., Katzogiannos, E. J. Biochem. Biophys. Methods (2004) [Pubmed]
  24. Ethanol production from olive oil extraction residue pretreated with hot water. Ballesteros, I., Oliva, J.M., Negro, M.J., Manzanares, P., Ballesteros, M. Appl. Biochem. Biotechnol. (2002) [Pubmed]
  25. Production of Tyrosol by Candida albicans Biofilms and Its Role in Quorum Sensing and Biofilm Development. Alem, M.A., Oteef, M.D., Flowers, T.H., Douglas, L.J. Eukaryotic Cell (2006) [Pubmed]
 
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