MENTHONE

Description

Menthone has a characteristic odor similar to menthol. May be prepared by oxidation of menthol.

Chemical properties

Menthone has a characteristic mint-like odor.

Occurrence

Reported found in severalstereoisomersin nature; l-menthone is a constituent of the essential oils of Russian and American peppermint, geranium, Andropogon gragrans, Mentha timija and Mentha arvensis; d-menthone is present in the essential oils of Barosma pulchellum, Nepeta japonica Maxim., and others. d-Isomenthone has been reported isolated from Micromeria abis sinica Benth., Pelargonium tomentosum Jacquin and others; l-isomenthone has been identified in Réunion geranium, Pelargonium capitau and others. Also reported found in lemon peel oil, black currants, celery seed, cinnamon, peppermint, cornmint, pennyroyal and other mentha oils, nutmeg, thymus, cocoa, mushrooms, starfruit, coriander leaf, rice, tarragon, calamus, buckwheat, sweet and bitter fennel, cherimoya, buchu oil, clam and sweet grass oil.

The Uses of MENTHONE

(±)-Menthone is a Menthol derivative. A volatile flavor compound found in human milk, red and black rice bran and specialty rice types.

Preparation

By oxidation of menthol.

Definition

ChEBI: (-)-menthone is a menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer). It is an enantiomer of a (+)-menthone.

Aroma threshold values

Detection: 170 ppb; aroma characteristics at 1.0%: minty, cooling, sweet, refreshing, peppermint fresh, slightly dirty woody, camphoraceous with a green herbal anise nuance.

Taste threshold values

Taste characteristics at 50 ppm: cooling, peppermint, fresh green, minty, herbal, dirty mentholic with a refreshing camphoraceous nuance.

Flammability and Explosibility

Not classified

Safety Profile

Moderately toxic by ingestion, intravenous, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Metabolism

H?m?l?inen (1912) claimed that menthone was probably oxidized in the rabbit to ketomenthone, since the glucuronide produced was converted by warm dilute H₂SO₄ to a substance which was probably △⁴⁽⁸ -p-menthen-3-one (pulegone). Williams (1940), however, showed that it underwent reduction in the rabbit with the production of d-neomenthol. The presence of l-menthol, the other possible reduction product, was not detected and it appeared that the biological reduction was asymmetric (Williams, 1959).