EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

2-methyl cyclohexanone
2-methylcyclohexanone

Sponsors

Name:2-methylcyclohexan-1-one
CAS Number: 583-60-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-513-6
FDA UNII:56E8224ZFJ
Nikkaji Web:J3.301D
Beilstein Number:0506751
MDL:MFCD00001635
XlogP3-AA:1.50 (est)
Molecular Weight:112.17184000
Formula:C7 H12 O
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Racemate.
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1102 2-methylcyclohexanone
FLAVIS Number:07.179 (Old)
DG SANTE Food Flavourings:07.179 2-methylcyclohexanone
FEMA Number:3946 2-methylcyclohexanone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 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 mm/Hg @ 25.00 °C. (est)
Flash Point: 116.00 °F. TCC ( 46.67 °C. )
logP (o/w): 1.356 (est)
Soluble in:
 alcohol
 water, 5142 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
minty peppermint cooling
Odor Description:at 10.00 % in dipropylene glycol. minty peppermint cooling
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-Methylcyclohexanone 98%
EMD Millipore
For experimental / research use only.
2-Methylcyclohexanone
Parchem
2-methyl cyclohexanone
Penta International
2-METHYLCYCLOHEXANONE
Santa Cruz Biotechnology
For experimental / research use only.
2-Methylcyclohexanone
Sigma-Aldrich
2-Methylcyclohexanone, ≥98%
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
2-Methylcyclohexanone >96.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 20 - Harmful by inhalation.
S 16 - Keep away from sources of ignition - No Smoking.
S 25 - Avoid contact with eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2140 ul/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

intraperitoneal-mouse LD50 200 mg/kg
National Technical Information Service. Vol. AD691-490

intravenous-mouse LDLo 270 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: CHANGE IN RATE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 633, 1953.

Dermal Toxicity:
skin-rabbit LD50 1770 ul/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

Inhalation Toxicity:
inhalation-rat LCLo 2800 ppm/4H
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

 
Safety in Use Information:
Category: flavor and fragrance agents
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
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 19
 average usual ppmaverage maximum ppm
baked goods: 10.0000025.00000
beverages(nonalcoholic): 5.0000010.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 50.00000100.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 5.0000010.00000
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: 25.0000050.00000
soups: --
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 51, (FGE.51)[1] - Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) and structurally related to alicyclic ketones, secondary alcohols and related esters evaluated by EFSA in FGE.09 (2004) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 51, Revision 1 (FGE.51Rev1): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by the JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev3 (2011)
View page or View pdf

Flavouring Group Evaluation 51, Revision 2 (FGE.51Rev2): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev6 (2015)
View page or View pdf

EPI System: View
NIOSH Pocket Guide:search
NLM Hazardous Substances Data Bank:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):583-60-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11419
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2297
WGK Germany:1
2-methylcyclohexan-1-one
Chemidplus:0000583608
EPA/NOAA CAMEO:hazardous materials
RTECS:GW1750000 for cas# 583-60-8
 
References:
 2-methylcyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:583-60-8
Pubchem (cid):11419
Pubchem (sid):134978234
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB31539
FooDB:FDB008147
Export Tariff Code:2914.29.5000
Haz-Map:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
camel grass oil
FR
cyclopentanone
FL/FR
laevo-mono
menthyl glutarate
FL/FR
laevo-
menthyl methyl ether
FL/FR
pinocarvone
FL/FR
aldehydic
aldehydic
iso
butyraldehyde
FL/FR
camphoreous
dextro-
camphor
FL/FR
camphor tree bark oil
FL/FR
herbal ethanone
FR
thujyl alcohol
FL/FR
citrus
ocimene quintoxide
FL/FR
earthy
3-
octanol
FL/FR
patchouli cyclohexanol
FR
floral
citronellal diisotridecyl acetal
FR
cyclohexyl ethyl acetate
FL/FR
cyclohexyl propanol
FR
2-
decalinol
FR
dihydrocarvyl acetate
FL/FR
2',4'-
dimethyl acetophenone
FL/FR
earthy indane
FR
floral methanol
FR
geranium oil china
FL/FR
menthadienyl formate
FR
muguet butanol
FR
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
fruity
2-
cyclopentyl cyclopentanone
FL/FR
lilac lactone
FL/FR
green
geranium absolute
FL/FR
thiogeraniol
FL/FR
herbal
barosma betulina leaf oil
FL/FR
1,4-
cineole
FL/FR
dehydroxylinalool oxide
FL/FR
iso
dihydrolavandulol
FR
(Z)-iso
dihydrolavandulyl acetate
FR
herbal undecanol
FR
hyssop oil
FL/FR
para-
menthane-3,8-diol
FL/FR
myrtenol
FL/FR
perillaldehyde
FL/FR
pine hexanol
FR
D-(+)-alpha-
pinene
FL/FR
piperitone
FL/FR
rosemary absolute
FL/FR
rosemary oil morocco
FL/FR
sabinene hydrate
FL/FR
viridiflorol
FL/FR
licorice
sweet
basil oleoresin
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil india
FL/FR
cornmint oil terpeneless
FL/FR
laevo-
menthol
FL/FR
(±)-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
dextro-neo
menthol
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
menthyl acetate
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
agathosma crenulata leaf oil
FL/FR
laevo-
carveol
FL/FR
laevo-
carvone
FL/FR
carvone
FL/FR
carvyl propionate
FL/FR
cyclohexanone
FR
dihydrocarveol
FL/FR
diosphenol
FL/FR
bitter
fennel seed oil
FR
dextro-2,8-para-
menthadien-1-ol
FL/FR
trans-para-2,8-1-
menthadienol
FL/FR
trans-para-
menthan-2-one
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
menthoxypropane diol
FL/FR
homo
menthyl acetate
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
peppermint oil terpenes
FR
beta-
phellandrene
FL/FR
piperitenone
FL/FR
laevo-
piperitone
FL/FR
iso
propyl tiglate
FL/FR
(-)-iso
pulegol
FL/FR
iso
pulegone
FL/FR
(R)-(+)-
pulegone
FR
iso
pulegyl formate
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
spicy
N,N-
diethyl octanamide
FR
laevo-
verbenone
FL/FR
sulfurous
buchu mercaptan
FL/FR
thujonic
armoise oil
FR
tropical
beta-
cyclocitral
FL/FR
woody
para-tert-
butyl cyclohexanone
FR
For Flavor
No flavor group found for these
laevo-
carveol
FL/FR
carvone
FL/FR
carvyl propionate
FL/FR
cyclopentanone
FL/FR
2-
cyclopentyl cyclopentanone
FL/FR
2',4'-
dimethyl acetophenone
FL/FR
(±)-N,N-
dimethyl menthyl succinamide
FL
diosphenol
FL/FR
lilac lactone
FL/FR
limonen-10-yl acetate
FL
dextro-2,8-para-
menthadien-1-ol
FL/FR
cis+trans-para-1(7)8-
menthadien-2-yl acetate
FL
trans-para-2,8-1-
menthadienol
FL/FR
para-
menthane-3,8-diol
FL/FR
3-laevo-
menthoxy-2-methyl propane-1,2-diol
FL
menthoxypropane diol
FL/FR
menthyl acetate racemic
FL/FR
laevo-mono
menthyl glutarate
FL/FR
laevo-
menthyl methyl ether
FL/FR
menthyl propylene glycol carbonate
FL
beta-
phellandrene
FL/FR
(Z,Z)-
photocitral A
FL
D-(+)-alpha-
pinene
FL/FR
pinocarvone
FL/FR
piperitenone
FL/FR
piperitenone oxide
FL
iso
pulegone
FL/FR
iso
pulegyl formate
FL/FR
laevo-
verbenone
FL/FR
viridiflorol
FL/FR
thujyl alcohol
FL/FR
aldehydic
aldehydic
iso
butyraldehyde
FL/FR
camphoreous
camphor tree bark oil
FL/FR
coffee
2-iso
propyl pyrazine
FL
cooling
1,4-
cineole
FL/FR
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
homo
menthyl acetate
FL/FR
menthyl acetate
FL/FR
sabinene hydrate
FL/FR
WS-5
FL
floral
dihydrocarvyl acetate
FL/FR
geranium oil china
FL/FR
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
green
cyclohexyl ethyl acetate
FL/FR
dihydrocarveol
FL/FR
geranium absolute
FL/FR
ocimene quintoxide
FL/FR
iso
propyl tiglate
FL/FR
herbal
2-
acetoxy-1,8-cineole
FL
barosma betulina leaf oil
FL/FR
hyssop oil
FL/FR
rosemary absolute
FL/FR
rosemary oil morocco
FL/FR
licorice
sweet
basil oleoresin
FL/FR
meaty
2-
methyl 3-(methyl thio) furan
FL
medicinal
dextro-
camphor
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil terpeneless
FL/FR
(±)-
menthol
FL/FR
dextro-neo
menthol
FL/FR
peppermint cyclohexanone
FL/FR
minty
agathosma crenulata leaf oil
FL/FR
laevo-
carvone
FL/FR
cornmint oil india
FL/FR
trans-para-
menthan-2-one
FL/FR
homo
menthol
FL/FR
(±)-iso
menthone
FL/FR
(-)-
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
myrtenol
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
dextro-
piperitone
FL/FR
piperitone
FL/FR
laevo-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
thiogeraniol
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
musty
3-
octanol
FL/FR
spicy
perillaldehyde
FL/FR
sulfurous
buchu mercaptan
FL/FR
tropical
beta-
cyclocitral
FL/FR
woody
dehydroxylinalool oxide
FL/FR
iso
pulegyl acetate
FL/FR
 
Potential Uses:
FL/FRcornmint
FRheather
FRherbal
FRmint
FRpeppermint
 
Occurrence (nature, food, other):note
 wine
Search Picture
 
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
 

Articles:

PubMed:ω-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.
 
Notes:
Used as a food additive [EAFUS]
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