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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:31:56 UTC
Update Date2021-10-13 06:56:12 UTC
HMDB IDHMDB0036396
Secondary Accession Numbers
  • HMDB36396
Metabolite Identification
Common Name3-Methylbutyl 3-oxobutanoate
Description3-Methylbutyl 3-oxobutanoate 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. 3-Methylbutyl 3-oxobutanoate is a sweet, ethereal, and fermented tasting compound. Based on a literature review very few articles have been published on 3-Methylbutyl 3-oxobutanoate.
Structure
Data?1563862869
Synonyms
ValueSource
3-Methylbutyl 3-oxobutanoic acidGenerator
3-Methylbutyl acetoacetateHMDB
3-Methylbutyl beta-ketobutyrateHMDB
Acetoacetic acid isoamyl esterHMDB
Acetoacetic acid, isopentyl esterHMDB
Butanoic acid, 3-oxo-, 3-methylbutyl esterHMDB
FEMA 3551HMDB
Isoamyl 3-oxobutanoateHMDB
Isoamyl acetoacetateHMDB
Isoamyl acetylacetateHMDB
Isoamyl beta-ketobutyrateHMDB
Isopentyl 3-oxobutanoateHMDB
Isopentyl acetoacetateHMDB
Isopentyl beta-ketobutyrateHMDB
Chemical FormulaC9H16O3
Average Molecular Weight172.2215
Monoisotopic Molecular Weight172.109944378
IUPAC Name3-methylbutyl 3-oxobutanoate
Traditional Name3-methylbutyl 3-oxobutanoate
CAS Registry Number2308-18-1
SMILES
CC(C)CCOC(=O)CC(C)=O
InChI Identifier
InChI=1S/C9H16O3/c1-7(2)4-5-12-9(11)6-8(3)10/h7H,4-6H2,1-3H3
InChI KeyXHRGPLDMNNGHCX-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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point89.00 to 91.00 °C. @ 6.00 mm HgThe Good Scents Company Information System
Water Solubility5708 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.740 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.27 g/LALOGPS
logP10(1.34) g/LALOGPS
logP10(1.76) g/LChemAxon
logS10(-1.9) g/LALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.73 m³·mol⁻¹ChemAxon
Polarizability19.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.0531661259
DarkChem[M-H]-136.31431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylbutyl 3-oxobutanoateCC(C)CCOC(=O)CC(C)=O1703.4Standard polar33892256
3-Methylbutyl 3-oxobutanoateCC(C)CCOC(=O)CC(C)=O1135.5Standard non polar33892256
3-Methylbutyl 3-oxobutanoateCC(C)CCOC(=O)CC(C)=O1215.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #1CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C1385.7Semi standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #1CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C1376.7Standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #2C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C1340.3Semi standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #2C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C1352.0Standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #1CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C1606.3Semi standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #1CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C1571.2Standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #2C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C1549.9Semi standard non polar33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #2C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C1546.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate EI-B (Non-derivatized)splash10-006x-9000000000-ea4087a7ea2378ba8ee92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate EI-B (Non-derivatized)splash10-006x-9000000000-ea4087a7ea2378ba8ee92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-b5a7a7f3fd77fcc5bcd52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate 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 - 3-Methylbutyl 3-oxobutanoate 10V, Positive-QTOFsplash10-05fr-5900000000-5b85793e472e00da5a902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Positive-QTOFsplash10-00di-9200000000-4b18b4fb8aefc4c94e582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Positive-QTOFsplash10-0603-9000000000-9911f00c3fa9b49f25f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Negative-QTOFsplash10-00e9-8900000000-4832666a5ea86a738fb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Negative-QTOFsplash10-0pc0-9400000000-5bddb9d4b2cecd4370cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Negative-QTOFsplash10-0a59-9000000000-948f0c139308a9081b892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Positive-QTOFsplash10-01bl-9400000000-9689ba6ae00740f4837e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Positive-QTOFsplash10-0006-9000000000-6a313710ef1adbcb0afd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Positive-QTOFsplash10-052f-9000000000-99bc67acbfcc650aa92c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Negative-QTOFsplash10-000i-9200000000-085ef9d84ed34f106b8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Negative-QTOFsplash10-0a4u-9400000000-5535ebb435ed224d3af42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Negative-QTOFsplash10-0a4i-9000000000-13316bf37cae9760e5be2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB015275
KNApSAcK IDNot Available
Chemspider ID55235
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61296
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1003181
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.. .