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Chemical Compound Review

SureCN57987     2-methoxy-4-prop-1-enyl-phenol

Synonyms: AG-C-94580, AG-G-10343, AG-G-11375, ANW-41708, AC1L1OJA, ...
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Disease relevance of Isoeugenol


High impact information on Isoeugenol


Chemical compound and disease context of Isoeugenol


Biological context of Isoeugenol

  • Clinical signs associated with isoeugenol exposure included dose-related evidence of sedation and aversion to treatment (rooting behavior) in all isoeugenol groups, as well as an increased incidence of piloerection at >/= 500 mg/kg/day [2].
  • Freeze-thaw cycles were effective in reducing cell numbers at isoeugenol concentrations down to 25 ppm [13].
  • These results indicate that isoeugenol therapy may not reverse diabetic oxidative stress in an overall sense [14].
  • The administration of methyl isoeugenol in the diet did not adversely affect the growth or general health of the animals or their food intakes [9].
  • DESIGN: We treated HGF and HSG cells with curcumin [1] and the related compounds biseugenol [2], eugenol [3], alpha-diisoeugenol [4], and isoeugenol [5] and measured cell survival (MTT method), ROS generation (DCFH-DA staining), and induction of early apoptosis [15].

Anatomical context of Isoeugenol


Associations of Isoeugenol with other chemical compounds


Gene context of Isoeugenol


Analytical, diagnostic and therapeutic context of Isoeugenol


  1. The time-dose-response relationship for elicitation of contact dermatitis in isoeugenol allergic individuals. Andersen, K.E., Johansen, J.D., Bruze, M., Frosch, P.J., Goossens, A., Lepoittevin, J.P., Rastogi, S., White, I., Menné, T. Toxicol. Appl. Pharmacol. (2001) [Pubmed]
  2. Evaluation of the developmental toxicity of isoeugenol in Sprague-Dawley (CD) rats. George, J.D., Price, C.J., Marr, M.C., Myers, C.B., Jahnke, G.D. Toxicol. Sci. (2001) [Pubmed]
  3. Characterization of S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri. Wang, J., Pichersky, E. Arch. Biochem. Biophys. (1998) [Pubmed]
  4. Isoeugenol: a survey of consumer patch-test sensitization. Thompson, G.R., Booman, K.A., Dorsky, J., Kohrman, K.A., Rothenstein, A.S., Schwoeppe, E.A., Sedlak, R.I., Steltenkamp, R.J. Food Chem. Toxicol. (1983) [Pubmed]
  5. 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]
  6. Characterization of a petunia acetyltransferase involved in the biosynthesis of the floral volatile isoeugenol. Dexter, R., Qualley, A., Kish, C.M., Ma, C.J., Koeduka, T., Nagegowda, D.A., Dudareva, N., Pichersky, E., Clark, D. Plant J. (2007) [Pubmed]
  7. Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers. Rajakumar, D.V., Rao, M.N. Biochem. Pharmacol. (1993) [Pubmed]
  8. 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]
  9. A 28-day feeding study with methyl isoeugenol in rats. Purchase, R., Ford, G.P., Creasy, D.M., Brantom, P.G., Gangolli, S.D. Food Chem. Toxicol. (1992) [Pubmed]
  10. Biotransformation of isoeugenol to vanillin by Pseudomonas putida IE27 cells. Yamada, M., Okada, Y., Yoshida, T., Nagasawa, T. Appl. Microbiol. Biotechnol. (2007) [Pubmed]
  11. Deodorants on the European market: quantitative chemical analysis of 21 fragrances. Rastogi, S.C., Johansen, J.D., Frosch, P., Menné, T., Bruze, M., Lepoittevin, J.P., Dreier, B., Andersen, K.E., White, I.R. Contact Derm. (1998) [Pubmed]
  12. Short term toxicity study in rats dosed with isoeugenol benzyl ether. Boe, M., Würtzen, G., Olsen, P. Drug and chemical toxicology. (1989) [Pubmed]
  13. A novel method for the reduction of numbers of Listeria monocytogenes cells by freezing in combination with an essential oil in bacteriological media. Cressy, H.K., Jerrett, A.R., Osborne, C.M., Bremer, P.J. J. Food Prot. (2003) [Pubmed]
  14. Effects of isoeugenol on oxidative stress pathways in normal and streptozotocin-induced diabetic rats. Rauscher, F.M., Sanders, R.A., Watkins, J.B. J. Biochem. Mol. Toxicol. (2001) [Pubmed]
  15. Induction of early apoptosis and ROS-generation activity in human gingival fibroblasts (HGF) and human submandibular gland carcinoma (HSG) cells treated with curcumin. Atsumi, T., Tonosaki, K., Fujisawa, S. Arch. Oral Biol. (2006) [Pubmed]
  16. Cytotoxicity and genotoxicity of methyleugenol and related congeners-- a mechanism of activation for methyleugenol. Burkey, J.L., Sauer, J.M., McQueen, C.A., Sipes, I.G. Mutat. Res. (2000) [Pubmed]
  17. Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers. Atsumi, T., Fujisawa, S., Satoh, K., Sakagami, H., Iwakura, I., Ueha, T., Sugita, Y., Yokoe, I. Anticancer Res. (2000) [Pubmed]
  18. Deodorants: an experimental provocation study with isoeugenol. Bruze, M., Johansen, J.D., Andersen, K.E., Frosch, P., Goossens, A., Lepoittevin, J.P., Rastogi, S.C., White, I., Menné, T. Contact Derm. (2005) [Pubmed]
  19. Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster. Munerato, M.C., Sinigaglia, M., Reguly, M.L., de Andrade, H.H. Mutat. Res. (2005) [Pubmed]
  20. Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? White, I.R., Johansen, J.D., Arnau, E.G., Lepoittevin, J.P., Rastogi, S., Bruze, M., Andersen, K.E., Frosch, P.J., Goossens, A., Menné, T. Contact Derm. (1999) [Pubmed]
  21. Isopanduratin A from Kaempferia pandurata as an active antibacterial agent against cariogenic Streptococcus mutans. Hwang, J.K., Chung, J.Y., Baek, N.I., Park, J.H. Int. J. Antimicrob. Agents (2004) [Pubmed]
  22. Correlations of patch test reactivity and the repeated open application test (ROAT)/provocative use test (PUT). Villarama, C.D., Maibach, H.I. Food Chem. Toxicol. (2004) [Pubmed]
  23. An odorant derivative as an antagonist for an olfactory receptor. Oka, Y., Nakamura, A., Watanabe, H., Touhara, K. Chem. Senses (2004) [Pubmed]
  24. A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Atsumi, T., Fujisawa, S., Tonosaki, K. Toxicology in vitro : an international journal published in association with BIBRA. (2005) [Pubmed]
  25. Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations. Ingvast-Larsson, J.C., Axén, V.C., Kiessling, A.K. Am. J. Vet. Res. (2003) [Pubmed]
  26. Evaluation of the sensitizing potential of eugenol and isoeugenol in mice and guinea pigs. Hilton, I., Dearman, R.J., Fielding, I., Basketter, D.A., Kimber, I. Journal of applied toxicology : JAT. (1996) [Pubmed]
  27. Surgical removal of an ovarian tumour in a koi carp (Cyprinus carpio). Raidal, S.R., Shearer, P.L., Stephens, F., Richardson, J. Aust. Vet. J. (2006) [Pubmed]
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