L(-)-Carvone

Description

L-(-)-Carvone is the principal odor component of spearmint. It is with a refreshingly cool, minty odor and taste. It is used as flavor ingredient in a variety of foods and beverages, as well as in toothpaste and mouthwash. It is used as a fragrance in personal care products. It is intended for use in the manufacture of an area repellent for mosquitoes and biting flies. L-(-)-carvone is also used in agriculture as a sprout inhibitor of potatoes.

References

[1] Charles S Sell, The Chemistry of Fragrances: From Perfumer to Consumer, 2nd Edition, 2006
[2] https://www.epa.gov
[3] K. J. Hartmans, P. Diepenhorst, W. Bakker and L. G. M. Gorris, The use of carvone in agriculture: sprout suppression of potatoes and antifungal activity against potato tuber and other plant diseases, Industrial Crops and Products, 1995, vol. 4, 3-13

Chemical Properties

Caravone occurs in different forms. l-Carvone exhibits odor of spearmint, while d-carvone exhibits odor reminiscent of caraway.

Chemical Properties

clear colorless to pale yellow liquid

Occurrence

R-Carvone is the main substance in spearmint oil, also present in toothpastes; it is the cause of delayed-type allergy resulting in cheilitis, but Hansson et al. also described a case of angioedema of the lips appearing within minutes after contact with toothpaste, with an open test resulting in an immediate and strong reaction to carvone.

Uses

(R)-(-)-Carvone is used in the flavor and food industry such as chewing gum additives. It is used in air freshening products such as in essential oils as well as in aromatherapy and alternative medicine. It is used to prepare carvomenthol, carvomenthone, dihydrocarvone, carveol and limonene. It reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. It is also used as a mosquito repellent and prevent premature sprouting of potatoes. Further, it is employed as an important starting material for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1 and (4S,6R,7R)-trihydroxy-1-octyne derivatives. It is utilized as a vital raw material for the asymmetric total synthesis of natural products. In addition to this, it is used as a chiral starting material.

Definition

ChEBI: A carvone having (R) configuration.

Aroma threshold values

Detection: d-Carvone: 6.7 to 820 ppb; l-carvone: 2.7 to 600 ppb

General Description

(-)-Carvone, a monoterpene ketone which is the main active component of mentha plant species like Mentha spicata. It has antinociceptive activity which is found to be associated with decreased peripheral nerve excitability.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Carvone occurs in the dextro, levo and racemic form; l-carvone can be isolated from the essential oil of spearmint or is commercially synthesized from d-limonene; d-carvone is usually prepared by fractional distillation of oil of caraway, also from dillseed and dillweed oils, but this type differs in odor and flavors.