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

Description

PIPERITONE is a p-menthane monoterpenoid with a fresh minty camphor-like odor, naturally occurring in extracts of commercial oil of peppermint. It is a primary reference substance with assigned absolute purity, and its exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG, PIPERITONE is a cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6.

Uses

Used in Flavor and Fragrance Industry:
PIPERITONE is used as a flavoring agent for its fresh minty camphor-like odor, adding a unique scent to various food and beverage products.
Used in Pharmaceutical Industry:
PIPERITONE is used as a starting material in the synthesis of Thymol (T413000), a phenolic compound known for its antibacterial properties. This makes it valuable in the development of antimicrobial drugs and treatments.
Used in Chemical Synthesis:
PIPERITONE serves as a key intermediate in the synthesis of various chemical compounds, contributing to the production of a wide range of products across different industries.

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

• 1195-31-9 (+)-p-menth-1-ene 
• 108-24-7 acetic anhydride 
• 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 
• 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 
• 7732-18-5 water 
• 71-43-2 benzene 
• 65733-27-9 cis-piperitol 
• 7599-88-4 1,2,4-trihydroxy paramenthane 

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 
• 491-04-3 (1R*,6S*)-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 491-04-3 trans-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 490-99-3 DL-neomenthol 
• 15356-70-4 menthol 
• 854820-25-0 (+/-)-(1Ξ,4S)-1-hydroxyamino-p-menthan-3-one oxime 
• 109827-70-5 (+/-)-6-isopropyl-3-trans-styryl-cyclohex-2-enone 
• 70139-74-1 3-(4-methoxy-styryl)-6-isopropyl-cyclohex-2-enone 
• 89-83-8 thymol 
• 70139-73-0 p-menth-1-en-3-one thiosemicarbazone 
• 70139-76-3 1-p-Dimethyl-aminostyryl-4-isopropyl-1-cyclohexen-3-on 
• 3804-01-1 (1RS,2SR,3SR,4RS)-p-menthane-2,3-diol 

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).

Highly enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: Alternative synthesis of (-)-menthol

A highly enantioselective catalytic hydrogenation of cyclic enones was achieved by using the combination of a cationic Rh1 complex, (S)-5,5′-bis{di(3,5-di-tert-butyl-4-methoxyphenylphosphino)}-4, 4′-bi-1,3-benzodioxole (DTBM-SEGPHOS), and (CH2CH 2PPh3Br)2. The presence of an s-cis C=C bond isopropylidene moiety on the cyclic enone influenced the enantioselectivity of the hydrogenation. Thus, the hydrogenation of 3-alkyl-6-isopropylidene-2- cyclohexen-1-one, which contains both s-cis and s-trans enones, proceeded in excellent enantioselectivity (up to 98% ee). To obtain high enantio- and s-trans selectivities, the addition of a halogen source to the cationic Rh complex was the essential step. With the key step of the s-trans selective asymmetric hydrogenation of piperitenone, we demonstrated a new synthetic method for optically pure (-)-menthol via three atom-economical hydrogenations. Moreover, we found that the complete s-trans and s-cis C=C bond selective reactions were also realized by the proper choice of both the chiral ligands and halides.