2-methyl cyclohexanone
2-methylcyclohexanone
Identification
| Name | 2-methyl cyclohexanone |
| IUPAC | 2-methylcyclohexan-1-one |
| CAS Number | 583-60-8 |
| EINECS | 209-513-6 |
| FDA UNII | 56E8224ZFJ |
| Molecular Formula | C7 H12 O |
| Molecular Weight | 112.17184000 |
| MDL Number | MFCD00001635 |
| Nikkaji Number | J3.301D |
| Beilstein | 0506751 |
Regulatory
| JECFA Food Flavoring | 1102 2-methylcyclohexanone |
| DG SANTE Food Flavourings | 07.179 2-methylcyclohexanone |
| FEMA Number | 3946 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 583-60-8 ; 2-METHYLCYCLOHEXANONE |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 96.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.92400 to 0.92600 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.689 to 7.705 |
| Refractive Index | 1.44400 to 1.45000 @ 20.00 °C. |
| Boiling Point | 162.00 to 163.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 2.039000 mmHg @ 25.00 °C. (est) |
| Flash Point | 116.00 °F. TCC ( 46.67 °C. ) |
| logP (o/w) | 1.356 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 10.00 % in dipropylene glycol. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 2140 ul/kg |
| Dermal Toxicity | skin-rabbit LD50 1770 ul/kg |
| Inhalation Toxicity | inhalation-rat LCLo 2800 ppm/4H |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nCARDIAC: CHANGE IN RATE']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for 2-methyl cyclohexanone usage levels up to | 0.5000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.12 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.10 (μg/capita/day) |
| Structure Class | II |
| baked goods | 10.00000 |
| beverages(nonalcoholic) | 5.00000 |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 50.00000 |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 5.00000 |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | 25.00000 |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
cyclohexanone, 2-methyl-
cyclohexanone, 2-methyl-, (±)-
methyl anone
2-
methyl cyclohexan-1-one
alpha-
methyl cyclohexanone
o-
methyl cyclohexanone
ortho-
methyl cyclohexanone
2-
methyl-1-cyclohexanone
2-
methyl-cyclohexanone
2-
methylcyclohexan-1-one
2-
methylcyclohexanone
alpha-
methylcyclohexanone
o-
methylcyclohexanone
ortho-
methylcyclohexanone
sexton B
tetrahydro-o-cresol
PubMed:
Ï-Transaminases for the amination of functionalised cyclic ketones.
PubMed:
Clathrates of TETROL: Further Aspects of the Selective Inclusion of Methylcyclohexanones in Their Energetically Unfavorable Axial Methyl Conformations.
PubMed:
Changes in acaricidal potency by introducing functional radicals and an acaricidal constituent isolated from Schizonepeta tenuifolia.
PubMed:
Oxorhenium complexes bearing the water-soluble tris(pyrazol-1-yl)methanesulfonate, 1,3,5-triaza-7-phosphaadamantane, or related ligands, as catalysts for Baeyer-Villiger oxidation of ketones.
PubMed:
The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.
PubMed:
New 3H-indole synthesis by Fischer's method. Part I.
PubMed:
PREPARATION OF (S)-2-Allyl-2-methylcyclohexanone (Cyclohexanone, 2-methyl-2-(2-propen-1-yl)-, (2S)-).
PubMed:
Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones.
PubMed:
Evidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases.
PubMed:
Biotransformation of (+/-)-2-methylcyclohexanone by fungi.
PubMed:
High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability.
PubMed:
Lithium hexamethyldisilazide-mediated enolizations: influence of chelating ligands and hydrocarbon cosolvents on the rates and mechanisms.
PubMed:
Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer-Villiger oxidations of cyclic ketones.
PubMed:
Studies of the condensation of sulfones with ketones and aldehydes.
PubMed:
Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates.
PubMed:
Spectral and magnetic studies on manganese(II), cobalt(II) and nickel(II) complexes with Schiff bases.
PubMed:
Mixed crystals containing the dioxo complex [[Ph3SiO]2VO2]- and novel pentacoordinated oxoperoxo complex [[Ph3SiO]2VO(O2)]-: X-ray crystal structure and assessment as oxidation catalysts.
PubMed:
Reaction of ketones with lithium hexamethyldisilazide: competitive enolizations and 1,2-additions.
PubMed:
Lithium hexamethyldisilazide-mediated ketone enolization: the influence of hindered dialkyl ethers and isostructural dialkylamines on reaction rates and mechanisms.
PubMed:
Lithium diisopropylamide-mediated lithiations of imines: insights into highly structure-dependent rates and selectivities.
PubMed:
Ketone enolization by lithium hexamethyldisilazide: structural and rate studies of the accelerating effects of trialkylamines.
PubMed:
Lithium hexamethyldisilazide/triethylamine-mediated ketone enolization: remarkable rate accelerations stemming from a dimer-based mechanism.
PubMed:
Unfunctionalized, alpha-epimerizable nonracemic ketones and aldehydes can be accessed by crystallization-induced dynamic resolution of imines.
PubMed:
Differential responses to odorant analogs after recovery from nerve transection.
PubMed:
The Suzuki coupling reaction in the stereocontrolled synthesis of 9-cis-retinoic acid and its ring-demethylated analogues.
PubMed:
Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes.
PubMed:
Regulated workplace ketones and their interference in the PFBHA method for aldehydes.
PubMed:
Catalytic enantioselective protonation of lithium enolates with chiral imides
PubMed:
Microwave Spectrum of 2-Methylcyclohexanone.
PubMed:
Determination of 6s-trans conformation of retinal chromophore in sensory rhodopsin I and phoborhodopsin.
PubMed:
Carbonyl reductase activity exhibited by pig testicular 20 beta-hydroxysteroid dehydrogenase.
PubMed:
alpha-Nitration of Ketones via Enol Silyl Ethers. Radical Cations as Reactive Intermediates in Thermal and Photochemical Processes.
PubMed:
Structure of (+/-)-(2S,1'S)-2-[hydroxy(phenyl)methyl]-2-methylcyclohexanone, C14H1802.
PubMed:
STEREOCHEMICAL ASPECTS OF THE METABOLISM OF THE ISOMERIC METHYLCYCLOHEXANOLS AND METHYLCYCLOHEXANONES.
PubMed:
The reaction of phenylmagnesium bromide with 2-chloro-4-methylcyclohexanone.