We thank Dr. G. Brunner for NMR experiments, Dr. F. Kuhn and Dr. J. Schmid for MS data, K. Grman for odor-threshold determinations, A. E. Alchenberger and D. Lelievre for olfactory evaluations, the Center for Computing and Communication at the RWTH Aachen University for free computational time, and the state of North Rhine-Westphalia for funding.
Cassis Odor through Microwave Eyes: Olfactory Properties and Gas-Phase Structures of all the Cassyrane Stereoisomers and its Dihydro Derivatives†
Article first published online: 9 MAY 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 24, pages 5576–5580, June 6, 2011
How to Cite
Mouhib, H., Stahl, W., Lüthy, M., Büchel, M. and Kraft, P. (2011), Cassis Odor through Microwave Eyes: Olfactory Properties and Gas-Phase Structures of all the Cassyrane Stereoisomers and its Dihydro Derivatives . Angew. Chem. Int. Ed., 50: 5576–5580. doi: 10.1002/anie.201100937
- Issue published online: 1 JUN 2011
- Article first published online: 9 MAY 2011
- Manuscript Received: 7 FEB 2011
- North Rhine-Westphalia
- rotational spectroscopy;
- structure–activity relationships
A hint of cassis: By a combination of microwave spectroscopy and quantum chemistry, the gas-phase structures of the Cassyrane stereoisomers and its dihydro derivatives have been determined, and correlated with their olfactory properties. Superposition analyses of the structures (see picture; black Cassyrane, silver Oxane, red O, yellow S) reveal the importance of the 5S configuration on the cassis odor, with the 2S,5R isomers being the most intense.