Investigation of an Olfactoryly Active Ring-Like Conformer of a Chain-Type Odorant, (3S)-3,7-dimethyloctanal, by computer calculation and graphics

Autor: Ikuo Moriguchi, Shuichi Hirono, Fumiko Yoshii
Rok vydání: 1993
Předmět:
Zdroj: Helvetica Chimica Acta. 76:2279-2287
ISSN: 1522-2675
0018-019X
Popis: The odor of (3S)-3,7-dimethyloctanal, a chain-type odorant, has some resemblance to that of ethyl (1 R, 6S)-2,2,6-trimethylcyclohexane-1-carboxylate, a ring-type odorant. We investigated the ring-like conformers of (3S)-3,7-dimethyloctanal. Two approaches, (i) systematic conformational analysis and (ii) construction of the initial structure by referring to the structure of the ring-type odorant, were considered in the search for ring-like conformers of the chain-type odorant. As a result, it was found that two stable ring-like conformers of (3S)-3,7-dimethyloctanal, obtained from the two approaches, resembled conformers of ethyl (1R, 6S)-2,2,6-trimethylcyclohexane-1-carboxylate in their three-dimensional structural features. The shapes of the two ring-like ones were not exactly the same but were quite similar. Therefore, the two ring-like conformers were considered to approximate the olfactoryly active conformer that binds and stimulates the same odor receptor as that for ethyl (1R,6S)-2,2,6-trimethylcyclohexane-1-carboxylate. In addition, ring-like conformers of another chain-type odorant, 2-methylpent-2-enal, were investigated to check the validity of the calculation method used.
Databáze: OpenAIRE
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