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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:42:33 UTC
Update Date2021-10-13 08:25:02 UTC
HMDB IDHMDB0040165
Secondary Accession Numbers
  • HMDB40165
Metabolite Identification
Common NameButyl levulinate
DescriptionButyl levulinate belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Butyl levulinate is a bitter, caramel, and fruity tasting compound. Based on a literature review a significant number of articles have been published on Butyl levulinate.
Structure
Data?1563863499
Synonyms
ValueSource
Butyl levulinic acidGenerator
4-Ketopentanoic acid butyl esterHMDB
Butyl 4-ketovalerateHMDB
Butyl 4-oxopentanoateHMDB
Butyl acetylpropionateHMDB
Butyl laevulinateHMDB
FEMA 2207HMDB
Levulinic acid N-butyl esterHMDB
Levulinic acid, butyl esterHMDB
N-Butyl 4-oxopentanoateHMDB
N-Butyl laevulinateHMDB
N-Butyl levulinateHMDB
Pentanoic acid, 4-oxo-, butyl esterHMDB
Butyl 4-oxopentanoic acidGenerator
Chemical FormulaC9H16O3
Average Molecular Weight172.2215
Monoisotopic Molecular Weight172.109944378
IUPAC Namebutyl 4-oxopentanoate
Traditional Namebutyl 4-oxopentanoate
CAS Registry Number2052-15-5
SMILES
CCCCOC(=O)CCC(C)=O
InChI Identifier
InChI=1S/C9H16O3/c1-3-4-7-12-9(11)6-5-8(2)10/h3-7H2,1-2H3
InChI KeyISBWNEKJSSLXOD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Fatty acid ester
  • Fatty acyl
  • 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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point106.00 to 108.00 °C. @ 5.50 mm HgThe Good Scents Company Information System
Water Solubility4940 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.457 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.91 g/LALOGPS
logP10(1.36) g/LALOGPS
logP10(1.4) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)17.54ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.73 m³·mol⁻¹ChemAxon
Polarizability19.55 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]+140.09731661259
DarkChem[M-H]-137.41531661259
DeepCCS[M+H]+144.0730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Butyl levulinateCCCCOC(=O)CCC(C)=O1961.9Standard polar33892256
Butyl levulinateCCCCOC(=O)CCC(C)=O1169.2Standard non polar33892256
Butyl levulinateCCCCOC(=O)CCC(C)=O1276.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butyl levulinate,1TMS,isomer #1CCCCOC(=O)CC=C(C)O[Si](C)(C)C1459.0Semi standard non polar33892256
Butyl levulinate,1TMS,isomer #1CCCCOC(=O)CC=C(C)O[Si](C)(C)C1402.8Standard non polar33892256
Butyl levulinate,1TMS,isomer #2C=C(CCC(=O)OCCCC)O[Si](C)(C)C1418.1Semi standard non polar33892256
Butyl levulinate,1TMS,isomer #2C=C(CCC(=O)OCCCC)O[Si](C)(C)C1405.0Standard non polar33892256
Butyl levulinate,1TBDMS,isomer #1CCCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C1668.1Semi standard non polar33892256
Butyl levulinate,1TBDMS,isomer #1CCCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C1614.8Standard non polar33892256
Butyl levulinate,1TBDMS,isomer #2C=C(CCC(=O)OCCCC)O[Si](C)(C)C(C)(C)C1617.9Semi standard non polar33892256
Butyl levulinate,1TBDMS,isomer #2C=C(CCC(=O)OCCCC)O[Si](C)(C)C(C)(C)C1594.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butyl levulinate EI-B (Non-derivatized)splash10-0007-9000000000-dd754b510d9a5b9646182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butyl levulinate EI-B (Non-derivatized)splash10-0007-9000000000-dd754b510d9a5b9646182018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl levulinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9000000000-2aa9aa6898ccc66696af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl levulinate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl levulinate 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 - Butyl levulinate 10V, Positive-QTOFsplash10-0ab9-4900000000-3b30aa503d4b32ce4e182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 20V, Positive-QTOFsplash10-0a4i-9200000000-c275c9ef2dd4689bbe7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 40V, Positive-QTOFsplash10-0a4l-9000000000-5fb37db543ff458e2c032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 10V, Negative-QTOFsplash10-00dj-7900000000-eb3fb3bd06b7a50ba5b92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 20V, Negative-QTOFsplash10-00r2-9600000000-cae40c7bc236f0fa944f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 40V, Negative-QTOFsplash10-0002-9000000000-ae41ac4c19ae4a4bf2b32016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 10V, Positive-QTOFsplash10-0aba-9200000000-b1bce0e3a06994d6dc4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 20V, Positive-QTOFsplash10-0ac3-9000000000-4f2ab0be26cee0b64cb32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 40V, Positive-QTOFsplash10-0a4l-9000000000-34ab516a8864b5b5fb152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 10V, Negative-QTOFsplash10-00dj-9000000000-f301c1f868e7fb9a2c552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 20V, Negative-QTOFsplash10-052e-9200000000-e74fbd3beb52ecbd8ea52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl levulinate 40V, Negative-QTOFsplash10-0a4l-9000000000-741689e5fae24b15ecc92021-09-24Wishart 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
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 IDFDB019874
KNApSAcK IDNot Available
Chemspider ID15496
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16331
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1013561
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.. .