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).
Uses
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.
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).
Preparation
By hydrogénation of piperitone.
Definition
ChEBI: (-)-isomenthone is an isomenthone. It is an enantiomer of a (+)-isomenthone.
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).
