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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:49 UTC
Update Date2021-10-13 04:41:09 UTC
HMDB IDHMDB0003315
Secondary Accession Numbers
  • HMDB03315
Metabolite Identification
Common NameCyclohexanone
DescriptionCyclohexanone 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 manufacturing 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; 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 approximately 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; 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 ).
Structure
Data?1582752269
Synonyms
ValueSource
Cyclohexyl ketoneChEBI
KetocyclohexaneChEBI
KetohexamethyleneChEBI
OxocyclohexaneChEBI
ANONHMDB
AnoneHMDB
CicloesanoneHMDB
Cyclic ketoneHMDB
CyclohexanonHMDB
Cyclohexanone homopolymerHMDB
CykloheksanonHMDB
HexanonHMDB
Hytrol OHMDB
HytroloHMDB
NadoneHMDB
Pimelic ketoneHMDB
Pimelin ketoneHMDB
Rcra waste number u057HMDB
SextoneHMDB
Chemical FormulaC6H10O
Average Molecular Weight98.143
Monoisotopic Molecular Weight98.073164942
IUPAC Namecyclohexanone
Traditional Namecyclohexanone
CAS Registry Number108-94-1
SMILES
O=C1CCCCC1
InChI Identifier
InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
InChI KeyJHIVVAPYMSGYDF-UHFFFAOYSA-N
Chemical Taxonomy
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

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling Point154.00 to 156.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility25 mg/mL at 25 °CNot Available
LogP0.81HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.6 g/LALOGPS
logP10(1.03) g/LALOGPS
logP10(1.49) g/LChemAxon
logS10(-0.7) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.78331661259
DarkChem[M-H]-113.77831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclohexanoneO=C1CCCCC11283.1Standard polar33892256
CyclohexanoneO=C1CCCCC1845.6Standard non polar33892256
CyclohexanoneO=C1CCCCC1886.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclohexanone,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC11116.1Semi standard non polar33892256
Cyclohexanone,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC11114.0Standard non polar33892256
Cyclohexanone,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC11295.8Standard polar33892256
Cyclohexanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC11308.5Semi standard non polar33892256
Cyclohexanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC11289.3Standard non polar33892256
Cyclohexanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC11503.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052b-9000000000-7f647b6a300fe214ba1c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-88641988de1851f0ca4a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-0a4l-9000000000-ef33444a3514a2701f272017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-e12b443f04b3874cc4a32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-6c26c5016354e3daff392017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-0a4m-9000000000-cc5c0d1047cc29ad45052017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052b-9000000000-7f647b6a300fe214ba1c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-88641988de1851f0ca4a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-0a4l-9000000000-ef33444a3514a2701f272018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-e12b443f04b3874cc4a32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-052f-9000000000-6c26c5016354e3daff392018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cyclohexanone EI-B (Non-derivatized)splash10-0a4m-9000000000-cc5c0d1047cc29ad45052018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclohexanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-676979762c05de37295f2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclohexanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-033d5d3e517e312e7ca42015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9000000000-ca81dd5928fb0f8c16fc2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0036-9000000000-f3a92fc2703dc2e7ac492012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0036-9000000000-96a8b1e4fcd8526498c72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (VARIAN MAT-44) , Positive-QTOFsplash10-052b-9000000000-61827fde8b35540ae2362012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-052f-9000000000-88641988de1851f0ca4a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0a4l-9000000000-a54e798882ebeac562d52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (JEOL JMS-D-3000) , Positive-QTOFsplash10-052f-9000000000-6a7154ca19de3cc987152012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (HITACHI M-80B) , Positive-QTOFsplash10-052f-9000000000-b22778e6dc417b973b8d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclohexanone EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-0a4m-9000000000-cc5c0d1047cc29ad45052012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 10V, Positive-QTOFsplash10-0002-9000000000-7d7a09c152ff6936e9062017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 20V, Positive-QTOFsplash10-0002-9000000000-1ccd9e64aac47d6a0d5b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 40V, Positive-QTOFsplash10-052f-9000000000-7df9b0d241ad009abf2f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 10V, Negative-QTOFsplash10-0002-9000000000-9faec66ab8e398a57ac82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 20V, Negative-QTOFsplash10-0002-9000000000-9faec66ab8e398a57ac82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 40V, Negative-QTOFsplash10-00kg-9000000000-7ab3d0ee8fbd2e7358052017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 10V, Negative-QTOFsplash10-0002-9000000000-21c5ae8d52f2e0f4cd332021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 20V, Negative-QTOFsplash10-0002-9000000000-be188196f07ccf1be01c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 40V, Negative-QTOFsplash10-0002-9000000000-f4aaa1a445ebe821a9862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 10V, Positive-QTOFsplash10-0532-9000000000-b4fe4dffc288586a2cdc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 20V, Positive-QTOFsplash10-0a4i-9000000000-f7bae72cd20f0ffb53902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclohexanone 40V, Positive-QTOFsplash10-0a4i-9000000000-76725ae76099c3e8afc02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDDB02060
Phenol Explorer Compound IDNot Available
FooDB IDFDB003418
KNApSAcK IDC00052902
Chemspider ID7679
KEGG Compound IDC00414
BioCyc IDCYCLOHEXANONE
BiGG IDNot Available
Wikipedia LinkCyclohexanone
METLIN IDNot Available
PubChem Compound7967
PDB IDNot Available
ChEBI ID17854
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1098591
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zheng M, McErlane KM, Ong MC: Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient. Xenobiotica. 2002 May;32(5):427-39. [PubMed:12065064 ]
  2. Authors unspecified: Cyclohexanone. IARC Monogr Eval Carcinog Risks Hum. 1999;71 Pt 3:1359-64. [PubMed:10476412 ]
  3. Muttray A, Haxel B, Mann W, Letzel S: [Toxic anosmia and rhinitis due to occupational solvent exposure]. HNO. 2006 Nov;54(11):883-7. [PubMed:16477465 ]
  4. Walker R, Flanagan RJ, Lennard MS, Mills GA, Walker V: Solid-phase microextraction: investigation of the metabolism of substances that may be abused by inhalation. J Chromatogr Sci. 2006 Aug;44(7):387-93. [PubMed:16925936 ]