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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:49 UTC
Update Date2017-10-23 19:04:02 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
Thumb
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
DescriptionThis compound 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

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility25 mg/mL at 25 °CNot Available
LogP0.81HANSCH,C ET AL. (1995)
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
Polarizability11.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052b-9000000000-7f647b6a300fe214ba1cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-88641988de1851f0ca4aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-ef33444a3514a2701f27View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-e12b443f04b3874cc4a3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-6c26c5016354e3daff39View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4m-9000000000-cc5c0d1047cc29ad4505View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-676979762c05de37295fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9000000000-ca81dd5928fb0f8c16fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0036-9000000000-f3a92fc2703dc2e7ac49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0036-9000000000-96a8b1e4fcd8526498c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-052b-9000000000-61827fde8b35540ae236View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-88641988de1851f0ca4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4l-9000000000-a54e798882ebeac562d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-052f-9000000000-6a7154ca19de3cc98715View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-b22778e6dc417b973b8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0a4m-9000000000-cc5c0d1047cc29ad4505View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-7d7a09c152ff6936e906View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-1ccd9e64aac47d6a0d5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-7df9b0d241ad009abf2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9faec66ab8e398a57ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-9faec66ab8e398a57ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-9000000000-7ab3d0ee8fbd2e735805View in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-033d5d3e517e312e7ca4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02060
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003418
KNApSAcK IDNot Available
Chemspider ID7679
KEGG Compound IDC00414
BioCyc IDCYCLOHEXANONE
BiGG IDNot Available
Wikipedia LinkCyclohexanone
METLIN IDNot Available
PubChem Compound7967
PDB IDCYH
ChEBI ID17854
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 ]