Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2019-11-26 02:58:51 UTC
Primary IDFDB003296
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Oxopentanoic acid
DescriptionLevulinic acid, also known as laevulinsaeure or levulate, 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. Levulinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Levulinic acid exists in all living organisms, ranging from bacteria to humans. Levulinic acid is a sweet, acetoin, and acidic tasting compound. Levulinic acid has been detected, but not quantified in, several different foods, such as cereals and cereal products, green vegetables, brassicas, root vegetables, and alcoholic beverages. This could make levulinic acid a potential biomarker for the consumption of these foods.
CAS Number123-76-2
Structure
Thumb
Synonyms
SynonymSource
3-Acetylpropionic acidChEBI
3-Ketobutane-1-carboxylic acidChEBI
4-Ketovaleric acidChEBI
4-Oxovaleric acidChEBI
beta-Acetylpropionic acidChEBI
gamma-Ketovaleric acidChEBI
LAEVULINIC ACIDChEBI
LaevulinsaeureChEBI
LEVAChEBI
Levulic acidChEBI
LevulinsaeureChEBI
3-AcetylpropionateGenerator
3-Ketobutane-1-carboxylateGenerator
4-KetovalerateGenerator
4-OxovalerateGenerator
b-AcetylpropionateGenerator
b-Acetylpropionic acidGenerator
beta-AcetylpropionateGenerator
Β-acetylpropionateGenerator
Β-acetylpropionic acidGenerator
g-KetovalerateGenerator
g-Ketovaleric acidGenerator
gamma-KetovalerateGenerator
Γ-ketovalerateGenerator
Γ-ketovaleric acidGenerator
LAEVULINateGenerator
LevulateGenerator
LevulinateGenerator
4-OxopentanoateHMDB
4-Oxopentanoic acidHMDB
DiasporalHMDB
Levulinic acid, sodium saltHMDB
Magnesium diasporalHMDB
Calcium levulateHMDB
Magnesium levulinateHMDB
Calcium levulinateHMDB
Levulinic acid, ammonium saltHMDB
Levulinic acid, calcium saltHMDB
Magnesium laevulinateHMDB
Levulinic acidChEBI
β-Acetylpropionic acidbiospider
Acetopropionic acidbiospider
Acetylpropionic acidbiospider
Centopropionic acidbiospider
FEMA 2627db_source
g-ketovaleric acidbiospider
Laevulic acidbiospider
Laevulinatebiospider
Laevulinic acidbiospider
Levulinic acid, 8CIdb_source
Pentanoic acid, 4-oxobiospider
Pentanoic acid, 4-oxo-biospider
Propionic acid, 3-acetyl-biospider
Valeric acid, 4-oxo-biospider
β-acetylpropionateGenerator
β-acetylpropionic acidGenerator
γ-ketovalerateGenerator
γ-ketovaleric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility139 g/LALOGPS
logP-0.14ALOGPS
logP-0.069ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.09 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H8O3
IUPAC name4-oxopentanoic acid
InChI IdentifierInChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyJOOXCMJARBKPKM-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CCC(O)=O
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
Classification
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
  • Short-chain keto acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 51.72%; H 6.94%; O 41.34%DFC
Melting PointMp 33.5°DFC
Boiling PointBp14 143-147°DFC
Experimental Water SolubilityNot Available
Experimental logP-0.49HANSCH,C ET AL. (1995)
Experimental pKapKa 4.62DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ug0-6900000000-ffad5af79457e68cca02JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-dd0d17209893b2b71d10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-0b0447e3daa65b1cd932JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e0d39a4a978220036faaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-6900000000-ffad5af79457e68cca02JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-beecc1bba7b8b0ca4201JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9500000000-8c1e2090296fa71bf0d0JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00xr-9400000000-923a1fccce36ba18d088JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01vo-9300000000-2c09d37e792efac90655JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0303-9800000000-d158f0c32e82eca0ef90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-dd0d17209893b2b71d10JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-9400000000-1043277f0ad49a5664a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9100000000-0a0fca12836c8c8ba113JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-247961be84518f0ebcdaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-b8133a0e2c97f98cef46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9600000000-e133b145c780f2c290d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9000000000-6ff5c46cdc591b725694JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID11091
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11579
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02239
HMDB IDHMDB00720
CRC / DFC (Dictionary of Food Compounds) IDCVR73-P:CVR73-P
EAFUS ID2019
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSHF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1016791
SuperScent IDNot Available
Wikipedia IDLevulinic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acidic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetoin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buttery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference