As the compound most responsible for the flavor of caraway, dill, and spearmint, carvone has been used for millennia in food.
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.
Its mirror image, S-(+)-carvone, has a spicy aroma with notes of rye, like caraway seeds.
S-(+)-Carvone is the principal constituent (60–70%) of the oil from caraway seeds (Carum carvi),[8] which is produced on a scale of about 10 tonnes per year.
Caraway was used for medicinal purposes by the ancient Romans,[3] but carvone was probably not isolated as a pure compound until Franz Varrentrapp (1815–1877) obtained it in 1849.
Goldschmidt and Zürrer identified it as a ketone related to limonene,[12] and the structure was finally elucidated by Georg Wagner (1849–1903) in 1894.
The levo-form obtained from the oils containing it usually requires additional treatment to produce high purity R-(−)-carvone.
This can be achieved by the formation of an addition compound with hydrogen sulfide, from which carvone may be regenerated by treatment with potassium hydroxide followed by steam distillation.
[2] In the presence of an alkali such as Ba(OH)2, carvone is oxidised by air or oxygen to give the diketone 7.
[16] Being available inexpensively in enantiomerically pure forms, carvone is 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:[17] In 1908, it was reported that exposure of carvone to "Italian sunlight" for one year gives carvone-camphor.