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Chemical Compound Review:

Isoeugenol 2-methoxy-4-[(E)-prop-1- enyl]phenol

Synonyms: iso-Eugenol 2, Isoeugenol E, Isoeugenol Z, Isoeugenol (I), AC1LGXFO, ...

Kalmes, M. et al., Koeduka, T. et al., Kilic, A. et al., Ghosh, R. et al.

Nadiminty, Hafizoglu, Kumar, Fitzpatrick, Nitz, Kollmannsberger, Alworth, Kilic, Ghosh, Slaga,

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Disease relevance of Isoeugenol

Eugenol but not its isomer, isoeugenol (2-methoxy-4-propenylphenol), was found to be a potent inhibitor of melanoma cell proliferation [1].
Fragrances such as eugenol (4-allyl-2-methoxyphenol) and isoeugenol (2-methoxy-4-propenylphenol), naturally found in reasonable quantities in the essential oils of different spices, are not only common causes of contact dermatitis but also known for their antiproliferative actions [2].

High impact information on Isoeugenol

Application of AEDA revealed (Z)-3-hexenal (fresh green), 1,8-cineole (eucalyptus), linalool (flowery), eugenol (clove), (E)-isoeugenol (flowery), and an unidentified compound (black pepper) with the highest flavor dilution factors [3].

Associations of Isoeugenol with other chemical compounds

We have obtained a cDNA encoding S-[methyl-14C]adenosyl-l-methionine:t-anol/isoeugenol O-methyltransferase 1 (AIMT1), an enzyme that can convert t-anol or isoeugenol to t-anethole or methylisoeugenol, respectively, via methylation of the para-OH group [4].

References

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]
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]
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L. Kilic, A., Hafizoglu, H., Kollmannsberger, H., Nitz, S. J. Agric. Food Chem. (2004) [Pubmed]
Biosynthesis of t-anethole in anise: characterization of t-anol/isoeugenol synthase and an O-methyltransferase specific for a C7-C8 propenyl side chain. Koeduka, T., Baiga, T.J., Noel, J.P., Pichersky, E. Plant Physiol. (2009) [Pubmed]

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