Enantioselectivity of the musk odor sensation.
This brief review, the summary of a talk at the Symposium on Biological Chirality 2000 in Szeged, Hungary, illustrates what chiral recognition tells us about the molecular parameters of the musk odor sensation. While the enantioselectivity of odor perception is strong evidence for the key role of proteinogenic receptors in the molecular mechanism of olfaction, the quantitative and qualitative odor differences of enantiomers are often not very pronounced, as in the case of muscone (17/26). In those cases, however, where there is strong enantiodiscrimination, we find most intense musk odorants with very low odor thresholds, such as (-)-(12R)-12-methyl-9-oxa-14-tetradecanolide (35), (12R;9Z)-12-methyl-14-tetradec-9-enolide [(R)-Nirvanolide, 38], and (-)-(4S;7R)-1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran [(-)-(4S;7R)-Galaxolide, 57], the latter being rather rigid. We thus can assume the geometry of the musk receptor to be fairly complementary to these compounds, which therefore can serve as templates for the design of new musk odorants.
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Givaudan Dübendorf Ltd., Fragrance Research, Uberlandstrasse 138, CH-8600 Dübendorf, Switzerland.
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D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D006801:Humans; D009812:Odorants; D018035:Receptors, Odorant / Q000737:chemistry / Q000502:physiology; D012903:Smell / Q000502:physiology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
D005229:Fatty Acids, Monounsaturated; D018035:Receptors, Odorant; C008563:musk