ISOMENTHONE

Occurrence

d-Isomenthone has been reported to have been isolated from Micromeria abissinica Benth., Pelargonium tomentosum Jacquin and others. /-Isomenthone has been identified in Reunion geranium, Pelargonium capitatum and others (FenaroWs Handbook of Flavor Ingredients, 1971).

The Uses of ISOMENTHONE

Isomenthone has very interesting effects in Rose, Carnation, Muguet, Fougeres, Lavender-complexes, etc. The use concentration will normally be about 0.5 to 200, but it may be somewhat higher in Rose and Lavender. The spicy notes in certain types of Men’s fragrances can eliminate the unpleasant sweetness brought about by the conventional Spice and Fougere fixatives.

Preparation

By hydrogénation of piperitone.

Definition

ChEBI: (-)-isomenthone is an isomenthone. It is an enantiomer of a (+)-isomenthone.

Production Methods

Isomenthone is produced 1) by isolation from Moroccan enny royal oil (dextro-Menthone). 2) by isolation from Congo Geranium oil (laevo-Menthone). 3) synthetic from 3-Methylcyclohexanone via its Glyoxylester and the corresponding Ketal to iso-Pulegone. This ketone is then treated with alcoholic Sodiumethylate to yield dl-pulegone, which is hydrogenated to iso-Menthone (dl-iso-Menthone).

Metabolism

d-Isomenthone undergoes reduction in the rabbit, since d-isomethylglucuronide is excreted in the urine. The other possible reduction product, d-neoisomenthol is not excreted (Williams, 1959).