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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:10 UTC
Update Date2019-07-23 06:08:26 UTC
HMDB IDHMDB0031295
Secondary Accession Numbers
  • HMDB31295
Metabolite Identification
Common NameEthyl pentyl ketone
DescriptionEthyl pentyl ketone, also known as 3-oxooctane or EAK, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Ethyl pentyl ketone has been detected, but not quantified in, cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1563862106
Synonyms
ValueSource
3-OxooctaneChEBI
Amyl ethyl ketoneChEBI
EAKChEBI
Ethyl amyl ketoneChEBI
Ethyl N-amyl ketoneChEBI
Ethyl N-pentyl ketoneChEBI
N-Amyl ethyl ketoneChEBI
Octan-3-oneChEBI
3-OctanonHMDB
3-OctanoneHMDB
Ethyl N-amylketoneHMDB
FEMA 2803HMDB
N-Octanone-3HMDB
Ethyl pentyl ketoneChEBI
Chemical FormulaC8H16O
Average Molecular Weight128.212
Monoisotopic Molecular Weight128.120115134
IUPAC Nameoctan-3-one
Traditional Name3-octanone
CAS Registry Number106-68-3
SMILES
CCCCCC(=O)CC
InChI Identifier
InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
InChI KeyRHLVCLIPMVJYKS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.6 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP2.61ALOGPS
logP2.84ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.25 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-781901ca764a5f841104Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-c5ad6888f5d8235bbcbdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-781901ca764a5f841104Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05bf-9000000000-c5ad6888f5d8235bbcbdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-c2c048174c4c8d3d8228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-ffaa377d52d739ba9f44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9400000000-f7381b3ecccb7b1c9936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-7f234320bd480d9871b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e4a3fd9e0a2d4bb13155Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-7900000000-5ba281eb40ef59122e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-9100000000-0ccdc24b3e039027a03aSpectrum
MSMass Spectrum (Electron Ionization)splash10-05i3-9000000000-91e0504d51c6adb6a6dcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005050
KNApSAcK IDC00034765
Chemspider ID215929
KEGG Compound IDC17145
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Octanone
METLIN IDNot Available
PubChem Compound246728
PDB IDNot Available
ChEBI ID80946
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .