PIPERITONE CAS 89-81-6

Introduction:Basic information about PIPERITONE CAS 89-81-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

PIPERITONE Basic information

Product Name:PIPERITONE
Synonyms:1-P-MENTHEN-3-ONE;4-ISOPROPYL-1-METHYL-1-CYCLOHEXEN-3-ONE;6-isopropyl-3-methylcyclohex-2-enone;P-MENTH-1-EN-3-ONE 92%;piperitone,3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one,p-menth-1-en-3-one;PIPERITONE(SG);ALPHA-PIPERITONE;PARA-MENTH-1-EN-3-ONE
CAS:89-81-6
MF:C10H16O
MW:152.23
EINECS:201-942-7
Product Categories:Biochemistry;Monocyclic Monoterpenes;Terpenes
Mol File:89-81-6.mol

PIPERITONE Chemical Properties

Melting point -29 °C
Boiling point 233°C
density 0,93 g/cm3
FEMA 2910 | D-PIPERITONE
refractive index -60 ° (C=4, benzene)
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Oil
color Colourless to Pale Yellow
Odorat 10.00 % in dipropylene glycol. herbal minty camphor medicinal
Odor Typeherbal
Merck 7473
JECFA Number435
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
InChIKeyYSTPAHQEHQSRJD-UHFFFAOYSA-N
SMILESCC(CCC1C(C)C)=CC1=O
LogP2.4
EPA Substance Registry SystemPiperitone (89-81-6)

Safety Information

Safety Statements 23-24/25
WGK Germany WGK 1
RTECS OT0257000
TSCA TSCA listed
HS Code 2914.29.5000
Storage Class10 - Combustible liquids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2

PIPERITONE Usage And Synthesis

Chemical PropertiesMonocyclic monoterpenes. There is a pair of enantiomers, both of which are naturally occurring. The right enantiomer has a camphoraceous odor, oily liquid, boiling point 232-235°C, relative density 0.9344, refractive index 1.4848, spin [α]20D +49.13°. Left spin body boiling point 109.5-110.5 ℃ (1.99kPa), relative density 0.9324, refractive index 1.4832, often in two optical isomers are present in a variety of essential oils.
UsesPiperitone 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. The cyclic ketone is more commonly used in flavour compositions, particularly in spice complexes with Caraway, Estragon, etc., and in fruit complexes with mint flavours, etc. Now and then, it has become “fashionable” in dentifrice preparations where larger amounts are used. The concentration normally used is equivalent to about 1 to 20 ppm in the finished product.
Production MethodsPiperitone 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.
DefinitionChEBI: 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.
General DescriptionThis 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.

PIPERITONE Preparation Products And Raw materials

Raw materialsSodium bisulfite-->Eucalyptus oil
Preparation ProductsMenthone-->ISOMENTHONE
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