ISOMENTHONE Chemical Properties

FEMA 

3460 | D,L-ISOMENTHONE

color 

A colourless slightly oily liquid

Odor

The powerful, refreshing and clean-minty odour of moderate tenacity. Somewhat cooling mouthfeel and a refreshing, minty, but distinctly bitter taste.

Water Solubility 

Almost insoluble in water, soluble in alcohol, Propylene glycol, mineral oil and perfume and flavour materials. Very poorly soluble in Glycerin.

Safety Information

Toxicity

The acute dermal LD 5 0 in rabbits was reported as > 5 ml/kg (Levenstein, 1973).

ISOMENTHONE Usage And Synthesis

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).

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