89-81-6

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 NO: 89-81-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 201-942-7
• Product Categories: Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 89-81-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: -29 °C
• Boiling Point: 233°C
• Flash Point: 90.9 ºC
• Appearance: clear, light yellowish to yellow liquid
• Density: 0,93 g/cm3
• Vapor Pressure: 0.0572mmHg at 25°C
• Refractive Index: -60 ° (C=4, benzene)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Merck: 7473
• CAS DataBase Reference: PIPERITONE(CAS DataBase Reference)
• NIST Chemistry Reference: PIPERITONE(89-81-6)
• EPA Substance Registry System: PIPERITONE(89-81-6)

Safety Data

• Safety Statements: 23-24/25
• RTECS: OT0257000
• Hazardous Substances Data: 89-81-6(Hazardous Substances Data)

Usage

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.

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

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3

Upstream product

• 94733-48-9 1-isopropyl-2-methoxy-4-methylcyclohexa-1,4-diene 
• 64049-39-4 3-(2-isopropyl-5-methyl-phenoxy)-propane-1,2-diol 
• 1195-31-9 (+)-p-menth-1-ene 
• 108-24-7 acetic anhydride 
• 29414-55-9 6,7-epoxymyrcene 
• 491-09-8 3-terpinolenone 
• 78871-90-6 1-Isopropyl-4-methyl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester 
• 78871-98-4 1-Isopropyl-2-methyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester 
• 112621-61-1 6-isopropyl-3-methyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one 
• 23033-91-2 (±)-2-isopropyl-5-methyl-4-hexenoic acid 
• 7664-93-9 sulfuric acid 
• 412314-19-3 2-acetyl-2-isopropyl-5-oxo-hexanoic acid ethyl ester 
• 861552-70-7 2-hydroxy-p-menthanone-⁽³⁾ 
• 64853-97-0 p-menth-6-en-3-one 

Downstream Products

• 91250-82-7 1-isopropyl-2,4-dimethyl-cyclohexa-1,3-diene 
• 3623-52-7 isomenthol 
• 118348-51-9 2-chloro-1-hydroxy-p-menthan-3-one 
• 1198-90-9 1-Methyl-3-ethyl-4-isopropyl-benzol 
• 4713-41-1 p-menth-1-en-3-one semicarbazone 
• 99-83-2 p-mentha-1,5-diene 
• 2543-54-6 2-isopropyl-5-oxohexanoic acid 
• 99-87-6 4-methylisopropylbenzene 
• 89-83-8 thymol 
• 34315-76-9 p-menthane-2,3-dione 
• 15840-87-6 3,3'-Dimethyl-6,6'-bis(1-methylethyl)-3,3'-bicyclohexanon 
• 15356-70-4 menthol 
• 108-39-4 3-methyl-phenol 
• 10458-14-7 Menthone 

Relevant articles and documents

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diastereoisomers (-)-38 and (-)-42.