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

cyclohexanone
ketohexamethylene

Supplier Sponsors

Name:cyclohexanone
CAS Number: 108-94-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-631-1
FDA UNII:5QOR3YM052
Nikkaji Web:J2.872J
Beilstein Number:0385735
MDL:MFCD00001625
CoE Number:11047
XlogP3:0.80 (est)
Molecular Weight:98.14490000
Formula:C6 H10 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:food contact microporous polymeric filters
 
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:1100 cyclohexanone
FLAVIS Number:07.148 (Old)
DG SANTE Food Flavourings:07.148 cyclohexanone
FEMA Number:3909 cyclohexanone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: CYCLOHEXANONE
FDA Regulation:
FDA PART 177 -- INDIRECT FOOD ADDITIVES: POLYMERS
Subpart C--Substances for Use Only as Components of Articles Intended for Repeated Use
Sec. 177.2250 Filters, microporous polymeric.
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.94700 to 0.95000 @ 25.00 °C.
Pounds per Gallon - (est).: 7.880 to 7.905
Refractive Index:1.44700 to 1.45300 @ 20.00 °C.
Melting Point: -47.00 °C. @ 760.00 mm Hg
Boiling Point: 154.00 to 156.00 °C. @ 760.00 mm Hg
Vapor Pressure:4.330000 mm/Hg @ 25.00 °C.
Vapor Density:3.4 ( Air = 1 )
Flash Point: 116.00 °F. TCC ( 46.67 °C. )
logP (o/w): 0.810
Soluble in:
 alcohol
 water, 2.408e+004 mg/L @ 25 °C (est)
 water, 2.50E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium ,
recommend smelling in a 1.00 % solution or less
minty acetone
Odor Description:at 1.00 % in dipropylene glycol. minty acetone
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
solvents
 
Suppliers:
Covalent Chemical
Cyclohexanone
EMD Millipore
For experimental / research use only.
Cyclohexanone
Indenta Group
Cyclohexanone
Lluch Essence
CYCLOHEXANONE 99%
Penta International
CYCLOHEXANONE REAGENT ACS GRADE, Kosher
Penta International
CYCLOHEXANONE, Kosher
Rainbow Chemical
Cyclohexanone 99.8
Santa Cruz Biotechnology
For experimental / research use only.
Cyclohexanone
Sigma-Aldrich
Cyclohexanone 99.8%
Certified Food Grade Products
Silver Fern Chemical
Cyclohexanone
Odor: characteristic
Use: Cyclohexanone is mainly used in the production of Nylon as a precursor to Nylon 6 and Nylon 6,6. It can also be used in the electronic industry, adhesives, agriculture, and paints.
TCI AMERICA
For experimental / research use only.
Cyclohexanone >99.0%(GC)
Wedor Corporation
CYCLOHEXANONE
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 20 - Harmful by inhalation.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
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 [sex: M,F] 1705 mg/kg
(Kohli et al., 1967)

oral-rat LD50 [sex: M,F] 1840 mg/kg
(Deichmann & LeBlanc, 1943)

oral-rat LD50 [sex: M,F] 1620 mg/kg
(Smyth et al., 1969a)

oral-rat LD50 [sex: M,F] 1800 mg/kg
(Gupta et al., 1979)

oral-mouse LD50 [sex: M,F] 2070 mg/kg
(Gupta et al., 1979)

gavage-rabbit LD50 [sex: M] 1600 mg/kg
(Treon et al., 1943)

intraperitoneal-rabbit LD50 [sex: M] 1540 mg/kg
(Gupta et al., 1979)

intraperitoneal-guinea pig LD50 [sex: M] 930 mg/kg
(Price, 1951)

intraperitoneal-guinea pig LDLo 760 mg/kg
National Technical Information Service. Vol. AD-A066-307

oral-mammal (species unspecified) LD50 3000 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.

intraperitoneal-mouse LD50 1230 mg/kg
GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.

oral-mouse LD50 1400 mg/kg
National Technical Information Service. Vol. AD-A066-307

intraperitoneal-rabbit LD50 1540 mg/kg
GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.

oral-rabbit LDLo 1600 mg/kg
BEHAVIORAL: GENERAL ANESTHETIC
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.

intraperitoneal-rat LD50 1130 mg/kg
GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.

oral-rat LD50 1620 uL/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

intravenous-rat LDLo 568 mg/kg
Toxicology and Applied Pharmacology. Vol. 37, Pg. 115, 1976.

Dermal Toxicity:
skin-rabbit LD50 1 ml/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

subcutaneous-rat LD50 2170 mg/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

subcutaneous-frog LDLo 1900 mg/kg
AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.

subcutaneous-mouse LDLo 1300 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.

subcutaneous-rat LD50 2170 mg/kg
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 415, 1943.

Inhalation Toxicity:
inhalation-rat LC50 8000 ppm/4H
Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 18, 1974.

inhalation-mammal (species unspecified) LC50 25000 mg/m3
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.

inhalation-guinea pig LCLo 400 ppm/4H
National Technical Information Service. Vol. AD-A066-307

inhalation-human TCLo 75 ppm
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.

inhalation-mouse TCLo 19200 mg/m3/90
GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.

 
Safety in Use Information:
Category: food contact microporous polymeric filters
 
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: 6.0000012.00000
beverages(nonalcoholic): 2.500005.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 100.00000200.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 2.000005.00000
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: 12.0000025.00000
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

Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
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
EPA-Iris:IRIS
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
NLM Hazardous Substances Data Bank:Search
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):108-94-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7967
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1915
WGK Germany:1
cyclohexanone
Chemidplus:0000108941
EPA/NOAA CAMEO:hazardous materials
RTECS:108-94-1
 
References:
 cyclohexanone
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:108-94-1
Pubchem (cid):7967
Pubchem (sid):134973338
Pherobase:View
 
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
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C00414
HMDB (The Human Metabolome Database):HMDB03315
FooDB:FDB003418
Export Tariff Code:2914.22.1000
FDA Listing of Food Additive Status:View
Haz-Map:View
Household Products:Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
Formulations/Preparations:
•technical: 99.8% •commercial: 89%; high purity: 99.5%
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 basil oil
Search Trop Picture
 brassica napus ssp. oleifera
Search Trop Picture
 cistus ladaniferus
Search Trop Picture
 musa spp.
Search Trop Picture
 passiflora mucronata
Search Trop Picture
 pepper bell pepper fruit
Search Trop Picture
 tea green tea
Search Trop Picture
 vriesea gladioliflora
Search Trop Picture
 
Synonyms:
 anon
 cyclohexyl ketone
 cycloyhexyl ketone
ketohexamethylene
 hexanon
 hytrol O
 nadone
 pimelic ketone
 pimelin ketone
 sextone
 

Articles:

PubMed:Effects of curcumin analogues for inhibiting human prostate cancer cells and the growth of human PC-3 prostate xenografts in immunodeficient mice.
PubMed:Synthesis and synergistic, additive inhibitory effects of novel spiro derivatives against ringworm infections.
PubMed:Changes in acaricidal potency by introducing functional radicals and an acaricidal constituent isolated from Schizonepeta tenuifolia.
PubMed:The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
PubMed:Ethambutol-mediated cell wall modification in recombinant Corynebacterium glutamicum increases the biotransformation rates of cyclohexanone derivatives.
PubMed:Major constituents and antimicrobial activity of Korean herb Acorus calamus.
PubMed:Behavioural and genetic evidence for C. elegans' ability to detect volatile chemicals associated with explosives.
PubMed:Characterization by volatile compounds of microbial deep spoilage in Iberian dry-cured ham.
PubMed:Productivity of cyclohexanone oxidation of the recombinant Corynebacterium glutamicum expressing chnB of Acinetobacter calcoaceticus.
PubMed:Stability of immobilized soybean lipoxygenase in selected organic solvent media.
PubMed:Synthesis and fungicidal activity of novel 2-oxocycloalkylsulfonylureas.
PubMed:Biologic evaluation of curcumin and structural derivatives in cancer chemoprevention model systems.
PubMed:In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
PubMed:Anomalous mutagenicity profile of cyclohexanone oxime in bacteria: cell survival in background lawns.
PubMed:A cyclohexanonyl bromophenol from the red alga Symphyocladia latiuscula.
PubMed:Orbital cortex neuronal responses during an odor-based conditioned associative task in rats.
PubMed:Migration from polyamide 'microwave and roasting bags' into roast chicken.
PubMed:Gas chromatographic determination of cyclohexanone leached from hemodialysis tubing.
PubMed:Metabolism of tetralin (1,2,3,4-tetrahydronaphthalene) in Corynebacterium sp. strain C125.
PubMed:Toxicity potential of compounds found in parenteral solutions with rubber stoppers.
PubMed:Capillary gas chromatographic determination of cyclohexanone and 2-ethyl-1-hexanol leached from solution administration sets.
PubMed:Hyperthermic and anorectic effects of oxazolidines derived from L-ephedrine in rats.
PubMed:Capillary GC analysis of compounds leached into parenteral solutions packaged in plastic bags.
PubMed:Prediction of ocular irritation by corneal pachymetry.
 
Notes:
Food flavourant. Present in various plant spp. e.g. Cistus ladaniferus (labdanum) Cyclohexanone is a colorless oily liquid with an odor resembling acetone and peppermint. Cyclohexanone is occasionally found as a volatile component of human urine. . Biological fluids such as blood and urine have been shown to contain a large number of components, some of them volatiles (low boiling point) apparently present in all individuals, while others such are much more variable. In some cases differences up to an order of magnitude are observed. Although some of these changes may have dietary origins, others seem to be characteristic of the individual. Cyclohexanone is obtained through oxidation of cyclohexane or dehydrogenation of phenol. Approx. 95% of its manuf. is used for the production of nylon. Information on toxicity to human beings is fragmentary. Acute exposure is characterized by irritation of the eyes, nose, and throat. In two persons, drowsiness and renal impairment were found; Like cyclohexanol, cyclohexanone is not carcinogenic and is only moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant.; The great majority of cyclohexanone is consumed in the production of precursors to Nylon 66 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 66. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to the oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:; however, there were embryotoxic effects and influence on reproduction Cyclohexanone is well absorbed through the skin, respiratory tract, and alimentary tract. The main metabolic pathway leads to cyclohexanol, which is excreted in urine coupled with glucuronic acid. A high correlation was found between the concentration of cyclohexanone in the working environment and its concentration in urine. Cyclohexanone is formed from the hydrocarbons cyclohexane and 1-, 2-, and 3-hexanol. A patient's case report documents the development of anosmia (an olfactory disorder) and rhinitis caused by occupational exposure to organic solvents, including cyclohexanone (PMID: 10476412, 16925936, 16477465); however, these workers were also exposed to other compounds. Hepatic disorders were found in a group of workers exposed for over five years. In animals, cyclohexanone is characterized by relatively low acute toxicity (DL50 by intragastric administration is approx. 2 g/kg body wt.). Effects on the central nervous system (CNS) were found (narcosis), as well as irritation of the eyes and skin. Following multiple administration, effects were found in the CNS, liver, and kidneys as well as irritation of the conjunctiva. Mutagenic and genotoxic effects were found, but no teratogenic effects were detected
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