Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi), spearmint (Mentha spicata), and dill. Uses Both carvones are used in the food and flavor industry. R-(−)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine. S-(+)-Carvone has shown a suppressant effect against high-fat diet induced weight gain in mice. Food applications As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. Wrigley's Spearmint Gum and spearmint flavored Life Savers are major users of natural spearmint oil from Mentha spicata. Caraway seed is extracted with alcohol to make the European drink Kümmel. Agriculture S-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name Talent. Insect control R-(−)-Carvone has been approved by the U.S. Environmental Protection Agency for use as a mosquito repellent. Organic synthesis Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products. For example, (S)-(+)-carvone was used to begin a 1998 synthesis of the terpenoid quassin:<ref>(a) Shing, T. K. M.; Jiang, Q; Mak, T. C. W. J. Org. Chem. 1998, 63, 2056-2057. (b) Shing, T. K. M.; Tang, Y. J. Chem. Soc. Perkin Trans. 1 1994, 1625.</ref> Stereoisomerism and odor Carvone forms two mirror image forms or enantiomers: R-(−)-carvone, or L-carvone, has a sweetish minty smell, like spearmint leaves. Its mirror image, S-(+)-carvone, or D-carvone, has a spicy aroma with notes of rye, like caraway seeds. The fact that the two enantiomers are perceived as smelling different is evidence that olfactory receptors must respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odors. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers. The two forms are also referred to by their optical rotations of laevo (L) referring to R-(−)-carvone, and dextro (D) referring to S-(+)-carvone. OccurrenceS-(+)-Carvone is the principal constituent (60–70%) of the oil from caraway seeds (Carum carvi), which is produced on a scale of about 10 tonnes per year. It also occurs to the extent of about 40–60% in dill seed oil (from