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Synthesis and Odor Characteristics of Some Cyclopentane Derivatives

Contact Author C. Wawrzebnczyk, S. Lochynski and J. Gora
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Continuing our studies on the relationship between structure and odor properties of the isoprenoid compounds, we took into consideration the influence of conformation of the isoprenoid chain on the odor. In our opinion, it seems that some information concerning this influence can be obtained by comparison of odors of acyclic compounds and their cyclic analogues. The additional C-C bond present in the cyclic analogues forces only some conformations of the isoprenoid chain. This type of the comparative study can be carried out only for pairs of acyclic and cyclic compounds which have the same number of the carbon atoms as well as functional groups.

In our previous paper we described the synthesis and odor characteristics of some gem-dimethylcyclohexane derivatives which were considered as cyclic analogues of dihydrocitronellol, dihydrogeraniol, menthocitronellol and their derivatives.

In this work we present the synthesis and odor characteristics of some cyclopentane derivatives. Compounds described in this paper can be considered as cyclic analogues of geraniol, citronellol, dihydrocitronellol and their derivatives. As it is shown in Figure 1, the isoprenoid chain in these compounds is folded in the cyclopentane ring by junction of two carbon atoms— C6 and C10.