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Record Information
Version3.6
Creation Date2006-05-22 15:12:49 UTC
Update Date2016-05-13 22:51:34 UTC
HMDB IDHMDB03315
Secondary Accession NumbersNone
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
ANONHMDB
AnoneHMDB
CicloesanoneHMDB
Cyclic ketoneHMDB
CyclohexanonHMDB
Cyclohexanone homopolymerHMDB
Cyclohexyl ketoneHMDB
CykloheksanonHMDB
HexanonHMDB
Hytrol OHMDB
HytroloHMDB
KetocyclohexaneHMDB
KetohexamethyleneHMDB
NadoneHMDB
OxocyclohexaneHMDB
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 KeyInChIKey=JHIVVAPYMSGYDF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexanones. These are compounds containing a cyclohexane moiety which bears a keto group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentCyclohexanones
Alternative Parents
Substituents
  • Cyclohexanone
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Signalling
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
logP1.03ALOGPS
logP1.49ChemAxon
logS-0.7ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.25 m3·mol-1ChemAxon
Polarizability11.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-033d5d3e517e312e7ca4View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
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
NuGOwiki LinkHMDB03315
Metagene LinkHMDB03315
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. [12065064 ]
  2. [No authors listed]Cyclohexanone. IARC Monogr Eval Carcinog Risks Hum. 1999;71 Pt 3:1359-64. [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. [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. [16925936 ]