(+)-Dihydrocarvone

Chemical Properties

p-Menth-8-en-2-one has an herbaceous, spearmint-like odor.

Occurrence

Reported present in oregano oil, celery, spearmint oil, scotch spearmint oil, thymus, dill herb and seed and caraway seed.

Uses

The dual, herbal-minty quality of this compound will add an interesting twist to mint flavors as well as to celery, caraway, dill and herbal flavors, especially intended for cough drops and oral care products. At very low levels, it will add depth to tropical flavors like lychee, guava, passion fruit and rambutan.

Uses

The N-functionalization of dihydrocarvone forms imine derivatives, which are synthons for preparing N-heterocycles.

Definition

ChEBI: A dihydrocarvone resulting from reduction of the endocyclic cyclohexene double bond.

Preparation

The production of cis-Dihydrocarvone: 1) by Isomerization of Limonene oxide. 2) from Dihydrocarveol by oxidation - or 3) from Carvone by reduction.

Aroma threshold values

Detection: 820 ppb to 1.06 ppm

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 2794, 1967 DOI: 10.1021/ja00987a087
Tetrahedron Letters, 30, p. 6567, 1989 DOI: 10.1016/S0040-4039(01)89023-7

General Description

Natural occurence: Caraway seed, celery seed, dill, patchouli, spearmint, buchu and pepper

Biochem/physiol Actions

Taste at 2-4ppm

Safety Profile

Moderately toxic by subcutaneous route. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.