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Cyclohexanone (FDB003418)

Record Information
Version1.0
Creation date2010-04-08 22:05:47 UTC
Update date2019-11-26 02:59:11 UTC
Primary IDFDB003418
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyclohexanone
DescriptionCyclohexanone is a 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
CAS Number108-94-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility19.6 g/LALOGPS
logP1.03ALOGPS
logP1.49ChemAxon
logS-0.7ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.25 m³·mol⁻¹ChemAxon
Polarizability11.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O
IUPAC namecyclohexanone
InChI IdentifierInChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
InChI KeyJHIVVAPYMSGYDF-UHFFFAOYSA-N
Isomeric SMILESO=C1CCCCC1
Average Molecular Weight98.143
Monoisotopic Molecular Weight98.073164942
Classification
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 73.43%; H 10.27%; O 16.30%DFC
Melting PointMp -45° (-32°)DFC
Boiling PointBp15 47°DFC
Experimental Water Solubility25 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.81HANSCH,C ET AL. (1995)
Experimental pKapKa 16.7DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.95DFC
Refractive Indexn20D 1.4500DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-033d5d3e517e312e7ca42015-03-01View Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052b-9000000000-7f647b6a300fe214ba1cSpectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-88641988de1851f0ca4aSpectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-ef33444a3514a2701f27Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e12b443f04b3874cc4a3Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-6c26c5016354e3daff39Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-0a4m-9000000000-cc5c0d1047cc29ad4505Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052b-9000000000-7f647b6a300fe214ba1cSpectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-88641988de1851f0ca4aSpectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-ef33444a3514a2701f27Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e12b443f04b3874cc4a3Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-6c26c5016354e3daff39Spectrum
GC-MSCyclohexanone, non-derivatized, GC-MS Spectrumsplash10-0a4m-9000000000-cc5c0d1047cc29ad4505Spectrum
Predicted GC-MSCyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-676979762c05de37295fSpectrum
Predicted GC-MSCyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9000000000-ca81dd5928fb0f8c16fc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0036-9000000000-f3a92fc2703dc2e7ac492012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0036-9000000000-96a8b1e4fcd8526498c72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-052b-9000000000-61827fde8b35540ae2362012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-88641988de1851f0ca4a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4l-9000000000-a54e798882ebeac562d52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-6a7154ca19de3cc987152012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-b22778e6dc417b973b8d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0a4m-9000000000-cc5c0d1047cc29ad45052012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-7d7a09c152ff6936e9062017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-1ccd9e64aac47d6a0d5b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-7df9b0d241ad009abf2f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9faec66ab8e398a57ac82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-9faec66ab8e398a57ac82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-9000000000-7ab3d0ee8fbd2e7358052017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-21c5ae8d52f2e0f4cd332021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-be188196f07ccf1be01c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-f4aaa1a445ebe821a9862021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0532-9000000000-b4fe4dffc288586a2cdc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-f7bae72cd20f0ffb53902021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-76725ae76099c3e8afc02021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID7679
ChEMBL IDCHEMBL18850
KEGG Compound IDC00414
Pubchem Compound ID7967
Pubchem Substance IDNot Available
ChEBI ID17854
Phenol-Explorer IDNot Available
DrugBank IDDB02060
HMDB IDHMDB03315
CRC / DFC (Dictionary of Food Compounds) IDCXZ75-T:CXZ75-T
EAFUS ID792
Dr. Duke IDCYCLOHEXANONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDCYH
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1098591
SuperScent IDNot Available
Wikipedia IDCyclohexanone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetone
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).