Enantiomers carvone

Ravid U, Bassat M, Putievsky E, Weinstein V, Ikan R, Isolation and determination of optically pure carvone enantiomers from caraway Carum carvi L.), diU Anethum aveolens L.), spearmint Mentha spicata L.) and Mentha longifolia (L.) Huds, Flavour Fragr J 2 95-97, 1987. 

Hormann CA, Cowart BJ, Olfactory discrimination of carvone enantiomers, Chem. Senses 18 573, 1993. 

Pike LM, Enns MP, Hornung DE, Quality and intensity differences of carvone enantiomers when tested separately and in mixtures, Chem Senses 13 307—309, 1988. 

For example, spearmint leaves and caraway seeds respectively contain L-carvone and D-carvone - enantiomers of carvone. These smell different to most people because our taste receptors also contain chiral molecules which behave differently in the presence of different enantiomers. 

Shown is the configuration of (+)-carvone. (+)-Carvone is the principal component of caraway seed oil and is responsible for its characteristic odor. (—)-Carvone, its enantiomer, is the main component of spearmint oil and gives it its characteristic odor. The fact that the carvone enantiomers do not smell the same su ests that the receptor sites in the nose for these compounds are chiral, and that only the correct enantiomer binds well to its particular site (just as a hand requires a glove of the correct chirality for a proper fit). Give the correct (R) and (5) designations for (+)- and (—)-carvone. 

Oosterhaven, K., K.J. Hartmans, and J.J.C. Scheffer, 1995a. Inhibition of potato sprouts growth by carvone enantiomers and their bioconversion in sprouts. Potato Res.. 38 219-230. 

The two carvone enantiomers are a prominent example. They differ in optical rotation, circular dichroism, and aroma impact. S-(+)-carvone with typical caraway... 

FIGURE 1.14. Structures of natural (—)-nicotine, a-(+)-lipoic acid, penicillin V, and carvone enantiomers. 

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