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Chemical Compound Review

eugenol     2-methoxy-4-prop-2-enyl-phenol

Synonyms: Engenol, Allylguaiacol, p-Eugenol, Eugenic acid, CCRIS 306, ...
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Disease relevance of eugenol


Psychiatry related information on eugenol

  • The association between the odor of eugenol and dental fear and anxiety could be explained by the fact that eugenates (eugenol-containing cements) are often used in potentially painful restorative dentistry on vital teeth [6].
  • These results suggest that eugenol may act by blocking Abeta-induced-Ca(2+) intake and provide a strong case for further pursuit of the therapeutic and prophylactic potentials of RAG and its active principles for the management of Alzheimer's disease [7].
  • In doing this, the psychometric properties of odor quality in the case of eugenol and citral are investigated using both discrimination (experiment 1) and scaling (experiment 2) [8].
  • Antioxidants such as eugenol and maltol may play an important role in the pharmaceutical activities of natural plant extracts used for aromatherapy [9].

High impact information on eugenol


Chemical compound and disease context of eugenol


Biological context of eugenol


Anatomical context of eugenol

  • Finally, the oxidation products of eugenol/peroxidase were observed to be highly cytotoxic using isolated rat hepatocytes as target cells [17].
  • The DNA adducts formed in HL-60 cells treated with eugenol were the same as those formed by in vitro peroxidase activation [15].
  • An analysis of the release and the diffusion through dentin of eugenol from zinc oxide-eugenol mixtures [18].
  • At a concentration higher than 3 mmol/L, eugenol was cytotoxic to oral mucosal fibroblasts in a concentration- and time-dependent manner [16].
  • Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages [19].

Associations of eugenol with other chemical compounds


Gene context of eugenol


Analytical, diagnostic and therapeutic context of eugenol

  • In a B16 xenograft study, eugenol treatment produced a significant tumor growth delay (p = 0.0057), an almost 40% decrease in tumor size, and a 19% increase in the median time to end point [1].
  • The other study examined the effects of 150 mg eugenol/d in capsule form, using a double-blind, placebo-controlled crossover design [27].
  • This study examined these responses in the ferret in more detail, both quantitatively and in three dimensions, 12 months after pulpectomy which was followed by obturation with gutta percha and zinc oxide and eugenol sealer [28].
  • The purity of several brands of eugenol was compared by using high performance liquid chromatography with a UV detector [29].
  • This seems to confirm the role of odors as elicitors of emotional memories and to support the possible influence of eugenol odor on the avoidance behavior of some subjects toward dental care [6].


  1. Eugenol causes melanoma growth suppression through inhibition of E2F1 transcriptional activity. Ghosh, R., Nadiminty, N., Fitzpatrick, J.E., Alworth, W.L., Slaga, T.J., Kumar, A.P. J. Biol. Chem. (2005) [Pubmed]
  2. Molecular cloning and expression of a cDNA encoding an olfactory-specific mouse phenol sulphotransferase. Tamura, H.O., Harada, Y., Miyawaki, A., Mikoshiba, K., Matsui, M. Biochem. J. (1998) [Pubmed]
  3. 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice. Phillips, D.H., Reddy, M.V., Randerath, K. Carcinogenesis (1984) [Pubmed]
  4. Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli. Overhage, J., Steinbüchel, A., Priefert, H. Appl. Environ. Microbiol. (2003) [Pubmed]
  5. Mechanisms of bactericidal action of cinnamaldehyde against Listeria monocytogenes and of eugenol against L. monocytogenes and Lactobacillus sakei. Gill, A.O., Holley, R.A. Appl. Environ. Microbiol. (2004) [Pubmed]
  6. Emotional responses evoked by dental odors: an evaluation from autonomic parameters. Robin, O., Alaoui-Ismaïli, O., Dittmar, A., Vernet-Maury, E. J. Dent. Res. (1998) [Pubmed]
  7. Rhizoma acori graminei and its active principles protect PC-12 cells from the toxic effect of amyloid-beta peptide. Irie, Y., Keung, W.M. Brain Res. (2003) [Pubmed]
  8. Psychometrics of odor quality discrimination: method for threshold determination. Olsson, M.J., Cain, W.S. Chem. Senses (2000) [Pubmed]
  9. Antioxidative activities of aroma extracts isolated from natural plants. Lee, K.G., Mitchell, A., Shibamoto, T. Biofactors (2000) [Pubmed]
  10. Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Koeduka, T., Fridman, E., Gang, D.R., Vassão, D.G., Jackson, B.L., Kish, C.M., Orlova, I., Spassova, S.M., Lewis, N.G., Noel, J.P., Baiga, T.J., Dudareva, N., Pichersky, E. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  11. Biotransformation of eugenol to ferulic acid by a recombinant strain of Ralstonia eutropha H16. Overhage, J., Steinbüchel, A., Priefert, H. Appl. Environ. Microbiol. (2002) [Pubmed]
  12. Saturated and monofluoro analogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast. Brennan, R.J., Kandikonda, S., Khrimian, A.P., DeMilo, A.B., Liquido, N.J., Schiestl, R.H. Mutat. Res. (1996) [Pubmed]
  13. Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT). Kalmes, M., Neumeyer, A., Rio, P., Hanenberg, H., Fritsche, E., Blömeke, B. Biol. Chem. (2006) [Pubmed]
  14. Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases. Gang, D.R., Beuerle, T., Ullmann, P., Werck-Reichhart, D., Pichersky, E. Plant Physiol. (2002) [Pubmed]
  15. Oxidation of eugenol to form DNA adducts and 8-hydroxy-2'-deoxyguanosine: role of quinone methide derivative in DNA adduct formation. Bodell, W.J., Ye, Q., Pathak, D.N., Pongracz, K. Carcinogenesis (1998) [Pubmed]
  16. Eugenol triggers different pathobiological effects on human oral mucosal fibroblasts. Jeng, J.H., Hahn, L.J., Lu, F.J., Wang, Y.J., Kuo, M.Y. J. Dent. Res. (1994) [Pubmed]
  17. Peroxidase-catalyzed oxidation of eugenol: formation of a cytotoxic metabolite(s). Thompson, D., Norbeck, K., Olsson, L.I., Constantin-Teodosiu, D., Van der Zee, J., Moldéus, P. J. Biol. Chem. (1989) [Pubmed]
  18. An analysis of the release and the diffusion through dentin of eugenol from zinc oxide-eugenol mixtures. Hume, W.R. J. Dent. Res. (1984) [Pubmed]
  19. Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages. Murakami, Y., Shoji, M., Hanazawa, S., Tanaka, S., Fujisawa, S. Biochem. Pharmacol. (2003) [Pubmed]
  20. Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK and apoptosis. Chainy, G.B., Manna, S.K., Chaturvedi, M.M., Aggarwal, B.B. Oncogene (2000) [Pubmed]
  21. An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Gang, D.R., Wang, J., Dudareva, N., Nam, K.H., Simon, J.E., Lewinsohn, E., Pichersky, E. Plant Physiol. (2001) [Pubmed]
  22. Ozone monitoring based on a biosensor concept utilizing a reagentless alcohol oxidase electrode. Stergiou, D.V., Prodromidis, M.I., Veltsistas, P.G., Evmiridis, N.P. Anal. Chem. (2006) [Pubmed]
  23. Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Kim, S.S., Oh, O.J., Min, H.Y., Park, E.J., Kim, Y., Park, H.J., Nam Han, Y., Lee, S.K. Life Sci. (2003) [Pubmed]
  24. Eugenol and its structural analogs inhibit monoamine oxidase A and exhibit antidepressant-like activity. Tao, G., Irie, Y., Li, D.J., Keung, W.M. Bioorg. Med. Chem. (2005) [Pubmed]
  25. Metabolic activation of eugenol by myeloperoxidase and polymorphonuclear leukocytes. Thompson, D., Constantin-Teodosiu, D., Norbeck, K., Svensson, B., Moldéus, P. Chem. Res. Toxicol. (1989) [Pubmed]
  26. Carvacrol and eugenol differentially stimulate intracellular Ca2+ mobilization and mitogen-activated protein kinases in Jurkat T-cells and monocytic THP-1 cells. Chan, A.S., Pang, H., Yip, E.C., Tam, Y.K., Wong, Y.H. Planta Med. (2005) [Pubmed]
  27. Do dietary phytochemicals with cytochrome P-450 enzyme-inducing activity increase high-density-lipoprotein concentrations in humans? Nanjee, M.N., Verhagen, H., van Poppel, G., Rompelberg, C.J., van Bladeren, P.J., Miller, N.E. Am. J. Clin. Nutr. (1996) [Pubmed]
  28. Periapical innervation of the ferret canine one year after pulpectomy. Holland, G.R. J. Dent. Res. (1992) [Pubmed]
  29. Analysis and purification of eugenol. Miller, R.A., Bussell, N.E., Ricketts, C.K., Jordi, H. J. Dent. Res. (1979) [Pubmed]
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