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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:14 UTC
Update Date2022-03-07 02:52:55 UTC
HMDB IDHMDB0031307
Secondary Accession Numbers
  • HMDB31307
Metabolite Identification
Common NameEthyl 3-oxohexanoate
DescriptionEthyl 3-oxohexanoate, also known as ethyl butyrylacetate, belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Ethyl 3-oxohexanoate is a sweet, berry, and fruity tasting compound. Based on a literature review very few articles have been published on Ethyl 3-oxohexanoate.
Structure
Data?1563862107
Synonyms
ValueSource
Ethyl butyrylacetateChEBI
Ethyl butyrylacetic acidGenerator
Ethyl 3-oxohexanoic acidGenerator
3-keto-N-Hexanoic acid ethyl esterHMDB
Ethyl alpha -butyrylacetateHMDB
Ethyl alpha-butyrylacetateHMDB
Ethyl beta-ketohexanoateHMDB
Ethyl butyroacetateHMDB
ETHYL-3-oxohexanoATEHMDB
FEMA 3683HMDB
Hexanoic acid, 3-oxo-, ethyl esterHMDB
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Nameethyl 3-oxohexanoate
Traditional Nameethyl 3-oxohexanoate
CAS Registry Number3249-68-1
SMILES
CCCC(=O)CC(=O)OCC
InChI Identifier
InChI=1S/C8H14O3/c1-3-5-7(9)6-8(10)11-4-2/h3-6H2,1-2H3
InChI KeyKQWWVLVLVYYYDT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point104.00 °C. @ 22.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP1.386 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.61 g/LALOGPS
logP1.22ALOGPS
logP1.65ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.28 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.55231661259
DarkChem[M-H]-133.45431661259
DeepCCS[M+H]+135.48630932474
DeepCCS[M-H]-132.88530932474
DeepCCS[M-2H]-169.58830932474
DeepCCS[M+Na]+144.61130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl 3-oxohexanoateCCCC(=O)CC(=O)OCC1691.9Standard polar33892256
Ethyl 3-oxohexanoateCCCC(=O)CC(=O)OCC1076.1Standard non polar33892256
Ethyl 3-oxohexanoateCCCC(=O)CC(=O)OCC1125.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethyl 3-oxohexanoate,1TMS,isomer #1CCCC(=CC(=O)OCC)O[Si](C)(C)C1315.9Semi standard non polar33892256
Ethyl 3-oxohexanoate,1TMS,isomer #1CCCC(=CC(=O)OCC)O[Si](C)(C)C1289.3Standard non polar33892256
Ethyl 3-oxohexanoate,1TMS,isomer #2CCC=C(CC(=O)OCC)O[Si](C)(C)C1303.3Semi standard non polar33892256
Ethyl 3-oxohexanoate,1TMS,isomer #2CCC=C(CC(=O)OCC)O[Si](C)(C)C1322.8Standard non polar33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #1CCCC(=CC(=O)OCC)O[Si](C)(C)C(C)(C)C1530.3Semi standard non polar33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #1CCCC(=CC(=O)OCC)O[Si](C)(C)C(C)(C)C1479.8Standard non polar33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #2CCC=C(CC(=O)OCC)O[Si](C)(C)C(C)(C)C1500.9Semi standard non polar33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #2CCC=C(CC(=O)OCC)O[Si](C)(C)C(C)(C)C1524.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl 3-oxohexanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9100000000-e6766bdb7a951bd05d992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl 3-oxohexanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl 3-oxohexanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Negative-QTOFsplash10-0bt9-4900000000-85a68c04e152bfe6051c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Negative-QTOFsplash10-000i-9300000000-ef4e1797c3297683c1b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Negative-QTOFsplash10-052g-9000000000-3dba4b28e998bd19bc372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Negative-QTOFsplash10-0btj-9800000000-ad7dc1c0ee764b0dea3f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Negative-QTOFsplash10-0006-9100000000-b849d27ad5b506736da02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Negative-QTOFsplash10-00kf-9000000000-a60379ee8c5705ef1e222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Positive-QTOFsplash10-0a4i-2900000000-164751d38a890ab5f3f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Positive-QTOFsplash10-01vn-9400000000-40b48fa60f02b0e6c2f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Positive-QTOFsplash10-0006-9000000000-2e3f07c039c725d96e5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Positive-QTOFsplash10-006x-9100000000-0d196847bba32addbf0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Positive-QTOFsplash10-00kf-9000000000-583a149a49c5c05382732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Positive-QTOFsplash10-0006-9000000000-06a898c67e0abcbc54a62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003363
KNApSAcK IDNot Available
Chemspider ID208322
KEGG Compound IDC02975
BioCyc IDETHYL-3-OXOHEXANOATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound238498
PDB IDNot Available
ChEBI ID18119
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1005531
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.. .