ISOMENTHONE Property

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

Toxicity

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

ISOMENTHONE Chemical Properties,Usage,Production

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).