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Olfactory study on optically active citronellyl derivatives
Author(s) -
Yamamoto Takeshi,
Shimada Akemi,
Ohmoto Tatsuya,
Matsuda Hiroyuki,
Ogura Miharu,
Kanisawa Tsuneyoshi
Publication year - 2004
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1280
Subject(s) - chemistry , diastereomer , ionone , enantiomer , monoterpene , stereochemistry , optically active , organic chemistry
Odour threshold concentrations, determined in agueous‐ethanol solution, and odour qualities are reported for 18 enantiomeric and diastereomeric pairs of citronellyl derivatives [13 linear monoterpene compounds and ve monocyclic α ‐damascone and α ‐ionone‐related compounds ( trans ‐2,2,6‐trimethylcyclohexyl derivatives)] (98%ee). Fairly large differences in both odour strength and odour qualities were found between the monocyclic diastereomeric pairs. In four of the ve cyclic compounds, the (1 R , 6 S )‐form was found to be stronger and more sensorily active than the antipode. On the other hand, the linear enantiomeric pairs showed only small differences in both odour strength (half of them showed the same threshold values) and odour character. However, all the (3 S )‐forms showed milder, cleaner and a much preferable top note than the (3 R )‐forms except for citronellyl nitrile and the diester (citronellyl ethyl oxalate), whose (3 R )‐form showed a characteristic oral musk odour, although the (3 S )‐form showed a rose oral odour. Copyright © 2004 John Wiley & Sons, Ltd.