15932-80-6

Basic information

• Product Name: 2-isopropylidene-5-methylcyclohexanone
• Synonyms: Cyclohexanone,5-methyl-2-(1-methylethylidene)-;PARA-MENTH-4(8)-EN-3-ONE;1-METHYL-4-ISOPROPYLIDENE-2-CYCLOHEXANONE;D-PARA-MENTH-4(8)-EN-3-ONE;Cyclohexanone,5-methyl-2-(;5-Methyl-2-(propan-2-ylidene)-cyclohexanone;5-Methyl-2-isopropylidenecyclohexanone;Chebi:26381
• CAS NO: 15932-80-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 240-070-1
• Mol File: 15932-80-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 234.73°C (rough estimate)
• Flash Point: 92.5°C
• Appearance: /
• Density: 0.9367
• Vapor Pressure: 0.0934mmHg at 25°C
• Refractive Index: 1.4869 (estimate)
• CAS DataBase Reference: 2-isopropylidene-5-methylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-isopropylidene-5-methylcyclohexanone(15932-80-6)
• EPA Substance Registry System: 2-isopropylidene-5-methylcyclohexanone(15932-80-6)

Safety Data

• Hazardous Substances Data: 15932-80-6(Hazardous Substances Data)

Usage

Description

2-Isopropylidene-5-methylcyclohexanone, also known as (RS)-Pulegone, is a p-menthane monoterpenoid with a cyclohexan-1-one structure. It is characterized by the presence of a methyl group at position 5 and a propan-2-ylidene group at position 2. This organic compound is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
2-Isopropylidene-5-methylcyclohexanone is used as an intermediate in the synthesis of Δ6a,10a-Tetrahydrocannabinol (T298635), a synthetic cannabinoid with psychoactive properties. Its role in the pharmaceutical industry is crucial for the development of new drugs and therapies that target specific medical conditions.
Used in Chemical Synthesis:
In the chemical industry, 2-Isopropylidene-5-methylcyclohexanone serves as a key intermediate in the synthesis of various compounds. Its unique structure allows for further chemical reactions and modifications, leading to the creation of new molecules with different properties and applications.
Used in Flavor and Fragrance Industry:
Due to its distinct chemical structure, 2-Isopropylidene-5-methylcyclohexanone can be used as a component in the flavor and fragrance industry. It can contribute to the development of new scents and flavors, enhancing the sensory experience of various products.
Used in Research and Development:
The compound's unique properties make it an interesting subject for research and development in various scientific fields. It can be used to study the effects of different functional groups on the properties of organic compounds and to explore new reaction pathways and mechanisms.

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3

Upstream product

• 91426-59-4 p-menth-8-en-3-one semicarbazone 
• 144-62-7 oxalic acid 
• 106-22-9 Citronellol 
• 36392-06-0 3,7-dimethyl-6-octenoyl chloride 
• 89-79-2 Isopulegol 
• 529-02-2 isopulegol 
• 57291-09-5 oxime E/Z de la methyl-5 (methyl-1 ethylidene)-2 cyclohexanone 
• 14252-45-0 2,2-bis(ethylthio)propane 
• 591-24-2 3-Methylcyclohexanone 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 29606-79-9 isopulegone 
• 7732-18-5 water 
• 141-52-6 sodium ethanolate 

Downstream Products

• 18368-85-9 1-butyl-2-isopropylidene-5-methyl-cyclohexanol 
• 78506-85-1 methylisopulegene 
• 13368-65-5 (3R)-3-methylcyclohexanone 
• 67-64-1 acetone 
• 56764-09-1 2-isopropylidene-1,5-dimethyl-cyclohexanol 
• 3058-01-3 3-methyladipic acid 
• 56763-63-4 (-)-6-isopropylidene-1,3-dimethyl-cyclohexene; (-)-methylpulegene 
• 56763-63-4 6-isopropylidene-1,3-dimethyl-cyclohexene 
• 18369-31-8 1-ethyl-2-isopropylidene-5-methyl-cyclohexanol 
• 16206-43-2 (-)-2-methyl-2-((1Ξ,4R)-4-methyl-2-oxo-cyclohexyl)-propionic acid 
• 626-51-7 3-methyl glutaric acid 
• 597-43-3 2,2-dimethylsuccinic acid 
• 99-82-1 Menthane 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 

Relevant articles and documents

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Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.

A versatile cobalt(II)-Schiff base catalyzed oxidation of organic substrates with dioxygen: Scope and mechanism

Cobalt(II) complex 1a-f derived from Schiff bases act as efficient catalysts during the oxidation of wide range of organic substrates(e.g. alkenes, alcohols, benzylic compounds and aliphatic hydrocarbons) with dioxygen in the presence of aliphatic aldehydes or ketones or ketoesters. EPR studies on 1a-f complexes suggest that the aliphatic carbonyl compounds promote the formation of a cobalt(II)-superoxo species responsible for the oxidation of organic compounds. These studies also demonstrate the role of ligands on cobalt in controlling the chemoselectivity of these oxidations. A plausible mechanistic rational is also provided for these oxidations.