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Skin Sensitization to Eugenol and Isoeugenol in Mice: Possible Metabolic Pathways Involving ortho-Quinone and Quinone Methide Intermediates

Skin Sensitization to Eugenol and Isoeugenol in Mice: Possible Metabolic Pathways Involving ortho-Quinone and Quinone Methide Intermediates. Bertrand, Franck; Basketter, David A.; Roberts, David W.; Lepoittevin, Jean-Pierre (Laboratoire de Dermatochimie associe au CNRS, Universite Louis Pasteur, Strasbourg F-67091, Fr.). Chemical Research in Toxicology, 10(3), 335-343 (English) 1997 American Chemical Society. CODEN: CRTOEC. ISSN: 0893-228X. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) With the aim of providing further mechanistic insights into the mode of action of eugenol (4-allyl-2-methoxyphenol) and isoeugenol (4-propenyl-2-methoxyphenol), we have synthesized two series of modified compds. which were tested in the mouse local lymph node assay for their skin sensitizing potential. The replacement of the methoxy group by an isopropoxy group led to a complete loss of sensitization for the eugenol deriv., while no significant effect was obsd. for the isoeugenol deriv. In the eugenol series, when Me groups were present in the 3-, 5-, or 6-position a significant redn. 7368-78-7 and 163429-79-6 are cas registry numbers of chemicals which are used as reagents here. in sensitization potential was obsd. while in the isoeugenol series only Me substitution in the 3- and 5-position had a discernable effect. Introduction of three Me groups on the arom. ring of eugenol (3,5,6-trimethyl-4-allyl-2-methoxyphenol) and of a tert-Bu substituent at the g-position of the alkyl chain of isoeugenol (4-[3',3',3'-trimethylpropenyl]-2-methoxyphenol) led to a strong decrease of the sensitizing capacity. Our findings indicate that, at least in the mouse, eugenol could sensitize via a demethylation pathway followed by oxidn. to the o-quinone which could act directly as a hapten even if we cannot exclude a reaction via its tautomeric p-quinone methide. Isoeugenol, could act via a mechanism not involving demethylation and for which the evidence is consistent with a direct oxidn. to the p-quinone methide. .