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Internet Electronic Journal of Molecular Design - IEJMD, ISSN 1538-6414, CODEN IEJMAT
| ABSTRACT - Internet Electron. J. Mol. Des. May 2004, Volume 3, Number 5, 241-246 |
Computer-Aided Synthesis of Dimerized Eugenol
Seiichiro Fujisawa, Mariko Ishihara, and Ichiro Yokoe
Internet Electron. J. Mol. Des. 2004, 3, 241-246
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Abstract:
Eugenol, an antioxidant is used as a fragrance, a flavoring agent,
and in dental materials. As an adverse effect, eugenol causes
allergic contact dermatitis, possibly due to its prooxidant activity
and the formation of eugenol-quinone methide (compound 1).
We recently reported that dimer of eugenol, dehydrodieugenol A
(compound 2) showed the less cytotoxicity and greater
antiinflammatory activity than parent eugenols. Therefore, we
examined high-yielding methods of producing dimers of
eugenol. Dimerization of eugenol was carried out in
CuCl(OH)/trimethylenediamine (TMEDA) in dichloromethane
in air at 20° C. Dimerization reaction pathway of eugenols was
evaluated from a PM3 semiempirical calculation. The simplicity
and excellent yield of approximately 79% made it the method of
choice for preparing this compound, 2. In contrast, compound 3,
dehydrodieugenol B was not synthesized from eugenols. The
experimental result was supported by the PM3 calculation, which
suggested that compound 3 could be synthesized from eugenols
with six-coordinating metals, but not with four-coordinating
metals such as copper. Dehydrodieugenol (2) was synthesized
from eugenols in approximately 79% yield. This dimerization
reaction pathway was estimated by the PM3 calculation.
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