Cassis Odor through Microwave Eyes: Olfactory Properties and Gas-Phase Structures of all the Cassyrane Stereoisomers and its Dihydro Derivatives

Authors

  • Dipl.-Chem. Halima Mouhib,

    1. Institute of Physical Chemistry, RWTH Aachen University, 52056 Aachen (Germany), Fax: (+49) 241-80-92365
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  • Prof. Dr. Wolfgang Stahl,

    Corresponding author
    1. Institute of Physical Chemistry, RWTH Aachen University, 52056 Aachen (Germany), Fax: (+49) 241-80-92365
    • Institute of Physical Chemistry, RWTH Aachen University, 52056 Aachen (Germany), Fax: (+49) 241-80-92365
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  • Dr. Monique Lüthy,

    1. Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, 8600 Dübendorf (Switzerland), Fax: (+41) 44-824-2926
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  • Michelle Büchel,

    1. Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, 8600 Dübendorf (Switzerland), Fax: (+41) 44-824-2926
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  • Dr. Philip Kraft

    Corresponding author
    1. Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, 8600 Dübendorf (Switzerland), Fax: (+41) 44-824-2926
    • Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, 8600 Dübendorf (Switzerland), Fax: (+41) 44-824-2926
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  • 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.

Abstract

original image

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.

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