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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-04-12 15:42:09 UTC
Update Date2021-10-13 04:47:39 UTC
HMDB IDHMDB0005846
Secondary Accession Numbers
  • HMDB05846
Metabolite Identification
Common NameEthyl isopropyl ketone
DescriptionEthyl isopropyl ketone, also known as 2-methyl-3-pentanal or 2-methylpentan-3-one, 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. Ethyl isopropyl ketone (or ethyl isopropyl ketone) is a volatile organic compound. Ethyl isopropyl ketone is a mint tasting compound. ethyl isopropyl ketone has been detected, but not quantified in corns. This could make ethyl isopropyl ketone a potential biomarker for the consumption of these foods. Volatile organic compounds from feces have the potential to help in the diagnosis of gastrointestinal disease. Ethyl isopropyl ketone is a component of the feces in the normal population and is also occasionally found as a volatile component of normal human biofluids. Ethyl isopropyl ketone is an aliphatic ketone used as a reagent in organic chemistry and as a solvent.
Structure
Data?1582752368
Synonyms
ValueSource
2-Methyl-3-pentanalHMDB
2-Methyl-3-pentanoneHMDB
2-Methylpentan-3-oneHMDB
4-Methyl-3-pentanoneHMDB
iso-C3H7COC2H5HMDB
Isopropyl ethyl ketoneHMDB
Chemical FormulaC6H12O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
IUPAC Name2-methylpentan-3-one
Traditional Name4-methyl-3-pentanone
CAS Registry Number565-69-5
SMILES
CCC(=O)C(C)C
InChI Identifier
InChI=1S/C6H12O/c1-4-6(7)5(2)3/h5H,4H2,1-3H3
InChI KeyHYTRYEXINDDXJK-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point113.5 °CNot Available
Water Solubility15.5 mg/mL at 25 °CNot Available
LogP1.331 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP1.45ALOGPS
logP2.05ChemAxon
logS-0.8ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings0ChemAxon
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]+121.31831661259
DarkChem[M-H]-116.92631661259
DeepCCS[M+H]+125.58830932474
DeepCCS[M-H]-123.46130932474
DeepCCS[M-2H]-159.31430932474
DeepCCS[M+Na]+134.08830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl isopropyl ketoneCCC(=O)C(C)C1009.2Standard polar33892256
Ethyl isopropyl ketoneCCC(=O)C(C)C714.8Standard non polar33892256
Ethyl isopropyl ketoneCCC(=O)C(C)C737.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethyl isopropyl ketone,1TMS,isomer #1CCC(O[Si](C)(C)C)=C(C)C983.2Semi standard non polar33892256
Ethyl isopropyl ketone,1TMS,isomer #1CCC(O[Si](C)(C)C)=C(C)C941.6Standard non polar33892256
Ethyl isopropyl ketone,1TMS,isomer #1CCC(O[Si](C)(C)C)=C(C)C974.6Standard polar33892256
Ethyl isopropyl ketone,1TMS,isomer #2CC=C(O[Si](C)(C)C)C(C)C926.4Semi standard non polar33892256
Ethyl isopropyl ketone,1TMS,isomer #2CC=C(O[Si](C)(C)C)C(C)C887.8Standard non polar33892256
Ethyl isopropyl ketone,1TMS,isomer #2CC=C(O[Si](C)(C)C)C(C)C1006.5Standard polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)=C(C)C1200.1Semi standard non polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)=C(C)C1142.2Standard non polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)=C(C)C1173.3Standard polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2CC=C(O[Si](C)(C)C(C)(C)C)C(C)C1142.6Semi standard non polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2CC=C(O[Si](C)(C)C(C)(C)C)C(C)C1121.0Standard non polar33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2CC=C(O[Si](C)(C)C(C)(C)C)C(C)C1196.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl isopropyl ketone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-169ad2a703b9155e87e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl isopropyl ketone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6u-9000000000-d28dd0d8a918e0f4cc662015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Positive-QTOFsplash10-0udi-3900000000-f8fe4280f501b51a75a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Positive-QTOFsplash10-0udi-8900000000-f29a5d1fc06f1e2646272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Positive-QTOFsplash10-0006-9000000000-af27439b3c00cb9f7f992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Negative-QTOFsplash10-0002-9000000000-0bab6124e7b3c3f342902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Negative-QTOFsplash10-0002-9000000000-a96b32781fe6fa58a9a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Negative-QTOFsplash10-05o0-9000000000-9f11e48c43be9ddf27462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Positive-QTOFsplash10-0f7o-9200000000-d9aa9c6699ef98b386a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Positive-QTOFsplash10-000x-9000000000-1596f7157a58311f21852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Positive-QTOFsplash10-0006-9000000000-2f31ecbea2ca586e81092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Negative-QTOFsplash10-0002-9000000000-658fe53778817eb823012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Negative-QTOFsplash10-0a4i-9000000000-d0bb07edc9d68aebeb9b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Negative-QTOFsplash10-0a4i-9000000000-6dd1cab74eba4bd803392021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007633
KNApSAcK IDC00052649
Chemspider ID10791
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl isopropyl ketone
METLIN IDNot Available
PubChem Compound11265
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1178591
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]