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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:17:45 UTC
Update Date2021-10-13 08:35:28 UTC
HMDB IDHMDB0041602
Secondary Accession Numbers
  • HMDB41602
Metabolite Identification
Common NameMethyl levulinate
DescriptionMethyl 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. Methyl levulinate is a caramellic tasting compound. Based on a literature review very few articles have been published on Methyl levulinate.
Structure
Data?1563863682
Synonyms
ValueSource
Methyl levulinic acidGenerator
4-Oxopentanoic acid, 9ciHMDB
Me esterHMDB
Methyl-4-oxopentanoateMeSH
Levulinic acid, methyl esterMeSH
Methyl-4-oxovalerateMeSH
Chemical FormulaC6H10O3
Average Molecular Weight130.143
Monoisotopic Molecular Weight130.062994182
IUPAC Namemethyl 4-oxopentanoate
Traditional Namemethyl 4-oxopentanoate
CAS Registry Number624-45-3
SMILES
COC(=O)CCC(C)=O
InChI Identifier
InChI=1S/C6H10O3/c1-5(7)3-4-6(8)9-2/h3-4H2,1-2H3
InChI KeyUAGJVSRUFNSIHR-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 methyl ester
  • Fatty acid ester
  • Fatty acyl
  • Methyl ester
  • 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 Point196.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility118600 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.130The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility62.3 g/LALOGPS
logP10(-0.17) g/LALOGPS
logP10(0.077) g/LChemAxon
logS10(-0.32) g/LALOGPS
pKa (Strongest Acidic)17.55ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.86 m³·mol⁻¹ChemAxon
Polarizability13.33 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]+130.06231661259
DarkChem[M-H]-125.30331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl levulinateCOC(=O)CCC(C)=O1631.2Standard polar33892256
Methyl levulinateCOC(=O)CCC(C)=O918.1Standard non polar33892256
Methyl levulinateCOC(=O)CCC(C)=O1019.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl levulinate,1TMS,isomer #1COC(=O)CC=C(C)O[Si](C)(C)C1191.6Semi standard non polar33892256
Methyl levulinate,1TMS,isomer #1COC(=O)CC=C(C)O[Si](C)(C)C1174.0Standard non polar33892256
Methyl levulinate,1TMS,isomer #2C=C(CCC(=O)OC)O[Si](C)(C)C1152.7Semi standard non polar33892256
Methyl levulinate,1TMS,isomer #2C=C(CCC(=O)OC)O[Si](C)(C)C1166.0Standard non polar33892256
Methyl levulinate,1TBDMS,isomer #1COC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C1404.5Semi standard non polar33892256
Methyl levulinate,1TBDMS,isomer #1COC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C1389.9Standard non polar33892256
Methyl levulinate,1TBDMS,isomer #2C=C(CCC(=O)OC)O[Si](C)(C)C(C)(C)C1361.8Semi standard non polar33892256
Methyl levulinate,1TBDMS,isomer #2C=C(CCC(=O)OC)O[Si](C)(C)C(C)(C)C1374.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-052b-9000000000-586bf3653d76af66925d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0006-9000000000-bb7c3071a74cb6e1f66a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0006-9100000000-820d538b4336c074ba522017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0007-9200000000-691ce72acd41e468f6822017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-052b-9000000000-586bf3653d76af66925d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0006-9000000000-bb7c3071a74cb6e1f66a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0006-9100000000-820d538b4336c074ba522018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl levulinate EI-B (Non-derivatized)splash10-0007-9200000000-691ce72acd41e468f6822018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl levulinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-a5e3492256d9057b1bd52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 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 - Methyl levulinate 10V, Positive-QTOFsplash10-001j-8900000000-b07b7980c4c1666bc5992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 20V, Positive-QTOFsplash10-01q9-9700000000-23b189cb24730f46cb7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 40V, Positive-QTOFsplash10-0kai-9000000000-5fd6a242c7e3979be5b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 10V, Negative-QTOFsplash10-004i-5900000000-d3767472eafdb4be55b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 20V, Negative-QTOFsplash10-004j-9700000000-8cea383ab923f84de0cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 40V, Negative-QTOFsplash10-000w-9000000000-96b153df7720ef8316002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 10V, Negative-QTOFsplash10-0002-9000000000-a402f567feda80d938cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 20V, Negative-QTOFsplash10-002g-9000000000-af6217f51c746dc5ebdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 40V, Negative-QTOFsplash10-0a4i-9000000000-dddd75eee962691434dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 10V, Positive-QTOFsplash10-06z3-9100000000-ea58db95fe8a20a230542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 20V, Positive-QTOFsplash10-0006-9000000000-14ff903aba73225f91772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl levulinate 40V, Positive-QTOFsplash10-0006-9000000000-6c214c00ddc82c2c1fe02021-09-23Wishart 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 IDFDB021756
KNApSAcK IDNot Available
Chemspider ID62563
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69354
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1046941
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.. .