Chemical Properties
monocyclic monoterpenoid. It exists as a pair of enantiomers, both of which occur naturally. The dextrorotatory enantiomer has a camphoraceous odor and is an oily liquid with a boiling point of 232-235°C, a relative density of 0.9344, a refractive index of 1.4848, and an optical rotation [α]20D +49.13°. The levorotatory enantiomer has a boiling point of 109.5-110.5°C (1.99 kPa), a relative density of 0.9324, and a refractive index of 1.4832. It often exists as two optical isomers in various essential oils.
Uses
Piperitone is a monoterpene compound that has a fresh minty camphor-like odour, and naturally occurs in extracts of commercial oil of peppermint. Piperitone is also used as a starting material in the synthesis of Thymol (T413000), a phenolic compound that is used for its antibacterial properties.
Definition
ChEBI: A p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6.
Production Methods
Piperitone is produced:
by isolation from Japanese Mint oil (dextro-Piperitone),
by isolation from Eucalyptus dives oil (laevo-Piperitone),
by hydrogenation of Diosphenol,
by reduction of 5-Methyl-2-iso-propylanisole with Sodium in liquid Ammonia.
laevo-Piperitone can also be produced from laevo-beta-Pinene via l-Limonene, by hydrogenation to /-Carvomenthene, and via 4 further intermediate steps to Piperitone.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
in vivo
The insecticidal activity of crude essential oil extracted from Cymbopogon schoenanthus and of its main constituent, Piperitone, is assessed on different developmental stages of Callosobruchus maculatus (C. maculatus). Piperitone is toxic to C. maculatus adults with a LC50 value of 1.6 μL/L. Piperitone inhibits the development of newly laid eggs and of neonate larvae, but is less toxic than the crude extract to individuals developing inside the seeds. Piperitone shows the strongest ovicidal activity. All the eggs were aborted at 6.7 μL/L. Piperitone (10 μM) kills all the neonate larvae[1].
| Animal Model: | Fifty pairs of C. maculatus adults[1] |
| Dosage: | 6.7, 10, 16.7 or 33.3 μL/L |
| Administration: | 24 hours |
| Result: | Piperiton was more toxic than crude oil because the LC50 recorded was 1.6 μL/L for Piperitone vs. 2.7 μL/L for the crude oil.
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