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Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | colorless clear liquid (est) |
| Assay: | 96.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 0.92400 to 0.92600 @ 25.00 °C.
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| Pounds per Gallon - (est).: | 7.689 to 7.705
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| Refractive Index: | 1.44400 to 1.45000 @ 20.00 °C.
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| Boiling Point: | 162.00 to 163.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 2.039000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 116.00 °F. TCC ( 46.67 °C. )
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| logP (o/w): | 1.356 (est) |
| Soluble in: |
| | alcohol | | | water, 5142 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| |
| Odor Type: minty |
| |
| | minty peppermint cooling |
Odor Description: at 10.00 % in dipropylene glycol. | minty peppermint cooling |
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
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.
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| 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.
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| Dermal Toxicity: |
skin-rabbit LD50 1770 ul/kg American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
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| Inhalation Toxicity: |
inhalation-rat LCLo 2800 ppm/4H American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
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Safety in Use Information:
| Category: | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment: Search |
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
| Recommendation for 2-methyl cyclohexanone usage levels up to: | | | 0.5000 % in the fragrance concentrate.
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| |
| 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 |
| Click here to view publication 19 |
| | average usual ppm | average maximum ppm |
| baked goods: | 10.00000 | 25.00000 |
| beverages(nonalcoholic): | 5.00000 | 10.00000 |
| beverages(alcoholic): | - | - |
| breakfast cereal: | - | - |
| cheese: | - | - |
| chewing gum: | 50.00000 | 100.00000 |
| condiments / relishes: | - | - |
| confectionery froastings: | - | - |
| egg products: | - | - |
| fats / oils: | - | - |
| fish products: | - | - |
| frozen dairy: | 5.00000 | 10.00000 |
| 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 | 50.00000 |
| soups: | - | - |
| sugar substitutes: | - | - |
| sweet sauces: | - | - |
Safety References:
References:
Other Information:
Potential Blenders and core components note
| |
| For Odor |
| No odor group found for these |
| | camel grass oil | FR |
| | cyclopentanone | FL/FR |
| | eucarvone | |
| | lippia alnifolia schau. leaf oil brazil | |
| laevo-mono | menthyl glutarate | FL/FR |
| laevo- | menthyl methyl ether | FL/FR |
| | pinocarvone | FL/FR |
| | satureja viminea oil costa rica | |
| | umbellulone | |
| 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 |
| | 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 |
| trans-para- | menthane-3,8-diol | |
| 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 |
| (±)- | menthol | FL/FR |
| dextro-neo | menthol | FL/FR |
| dextro,laevo- | menthol | FL/FR |
| laevo- | 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 |
| | camphene hydrate | |
| 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 |
| | mentha longifolia 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 |
| pine |
| | plectranthus glandulosus hook f. leaf oil cameroon | 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 |
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| For Flavor |
| |
| No flavor group found for these |
| | camphene hydrate | |
| | carvone | FL/FR |
| | cyclopentanone | FL/FR |
| 2- | cyclopentyl cyclopentanone | FL/FR |
| 2',4'- | dimethyl acetophenone | FL/FR |
| (±)-N,N- | dimethyl menthyl succinamide | FL |
| | eucarvone | |
| | lilac lactone | FL/FR |
| | limonen-10-yl acetate | FL |
| | lippia alnifolia schau. leaf oil brazil | |
| 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 |
| trans-para- | menthane-3,8-diol | |
| 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 |
| | satureja viminea oil costa rica | |
| | umbellulone | |
| laevo- | verbenone | FL/FR |
| | viridiflorol | FL/FR |
|
| | thujyl alcohol | FL/FR |
| aldehydic |
| iso | butyraldehyde | FL/FR |
| camphoreous |
| | camphor tree bark oil | FL/FR |
| coffee |
| 2-iso | propyl pyrazine | FL |
| cooling |
| 1,4- | cineole | FL/FR |
| dextro,laevo- | menthol | FL/FR |
| 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 |
| | thiogeraniol | 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 |
| dextro-neo | menthol | FL/FR |
| (±)- | menthol | FL/FR |
| | peppermint cyclohexanone | FL/FR |
| minty |
| | agathosma crenulata leaf oil | FL/FR |
| laevo- | carveol | FL/FR |
| laevo- | carvone | FL/FR |
| | carvyl propionate | FL/FR |
| | cornmint oil india | FL/FR |
| | diosphenol | 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 |
| laevo- | piperitone | FL/FR |
| | piperitone | FL/FR |
| dextro- | piperitone | FL/FR |
| (-)-iso | pulegol | 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 |
| 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 |
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Potential Uses:
Occurrence (nature, food, other): note
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. |
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