Carvone

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.

Carvone
Carvone
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
Various chemical reductions of carvone
Various chemical reductions of carvone
Various oxidations of carvone
Various oxidations of carvone
Methylation of carvone by Me2CuLi, followed by allylation by allyl bromide
Methylation of carvone by Me 2 CuLi, followed by allylation by allyl bromide
Asymmetric total synthesis of quassin from carvone
Asymmetric total synthesis of quassin from carvone