Menthone

Chemical Properties

CLEAR COLOURLESS LIQUID

Chemical Properties

Menthone exists as two stereoisomers, trans-menthone and cis-isomenthone, each of which occurs as a pair of enantiomers, due to the two asymmetric centers present in the molecule.
Both stereoisomers occur in many essential oils, often as a single enantiomer species. A particularly high concentration (sometimes >50%) is found in oils from Mentha species.Thementhones are colorless liquids that possess a typically minty odor; the odor of isomenthone is slightly musty.They have a strong tendency to interconvert and are, therefore, difficult to obtain in high purity. Industrial products aremixtures of varying composition.
The menthones are converted into the corresponding menthols by means of hydrogenation; for example, ()-menthone yields (+)-neomenthol and ()-menthol.
()-Menthone can be obtained by distillation of dementholized cornmint oil or by oxidation of ()-menthol (e.g., with chromic acid). Dehydrogenation of ()- menthol (e.g., with copper chromite) yields a mixture of ()-menthone and (+)- isomenthone.
rac-Menthone is prepared analogously to rac-menthol. However, it can also be synthesized by hydrogenation of thymol in the presence of palladium–carbon catalysts .
Menthone and isomenthone are used for synthetic peppermint oils and bases.

Uses

Menthone has been used in the following studies:

• To prepare the model flavor mix in a study to investigate the release of various aroma compounds in xanthan-thickened food model systems having different viscosities.
• As standard in the quantification of volatile constituents and odour-activity value (OAV) in ′Marion′ and ′Black Diamond′.
• Modified semisolid agar antifungal susceptibility method (SAAS) to investigate the anti-fungal activities of various cyclic terpenes against Fusarium verticillioides MRC 826.

Definition

ChEBI: P-menthan-3-one is a p-menthane monoterpenoid that is p-menthane substituted by an oxo group at position 3. It has a role as a plant metabolite and a volatile oil component.

Application

Menthone is used in flavor compositions, not only in Mint complexes, but in traces in fruit blends, particularly in imitation Raspberry, where it gives good lift and freshness in the otherwise oversweet composition. The concentration is normally about 5 to 50 ppm in the finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 5621, 1987 DOI: 10.1021/jo00234a021
Tetrahedron Letters, 13, p. 749, 1972

General Description

Menthone is a cyclic oxygenated terpene and its antioxidant potential has been evaluated. It is one of the key active component of Danshu capsule (DSC), a medicinal compound in traditional Chinese medicine.