Odors enantiomeric differences between

Russell, G. F. and Hills, J. I. (1971). Odor differences between enantiomeric isomers. Science 172,1043-1044. 

Friedman, L., Miller, J. G. 1971. "Odor Differences Between Enantiomeric Isomers." Science, 172 1043-1046. 

Friedman and Miller also established that synthetic R-(+) and S-(— ) limo-nene have the odor of oranges and lemons respectively. They also demonstrated the differences between other enantiomeric pairs such atR-(-f-) andS-(—) amphetamine. There remains no doubt that some enantiomeric pairs do have different odors. Whatever the nature of the sensory detector involved, it must, in order to be able to discriminate between enantiomeric pairs, itself be locally chiral. Hence... 

Leitereg, T. J., D. G. Guadagni, J. Harris, T. R. Mon, and R. Teranishi Chemical and Sensory Data Supporting the Difference Between the Odor of the Enantiomeric Carvones. J. Agric. Food Chem. 19, 785 (1971). 

Proteins are chiral, so they should interact differently with the two enantiomeric forms of a chiral molecule, which should eventually translate into a difference of the odor impression of these mirror images of the molecules. A more detailed knowledge of the relations between the chemical structure of a molecule, including its absolute configuration, and its odor properties will contribute to the elucidation of the receptor mechanism. 

Sensory receptors also readily distinguish enantiomers. The specificity of response is similar to the relationship between our hands and how they fit into gloves. Because sensory receptors are chiral, they interact stereospecifically with only one of a pair of enantiomers. The two enantiomeric forms of carvone have very different odors. (+)-Carvone is present in spearmint oil, imparting its odor. In contrast, its enantiomer, (-)-carvone, is present in caraway seed. It has the famihar odor associated with rye bread. 

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