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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 20:22:17 UTC
HMDB IDHMDB0000720
Secondary Accession Numbers
  • HMDB00720
Metabolite Identification
Common NameLevulinic 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 exists as a solid, soluble (in water), and a weakly acidic compound (based on its pKa). Levulinic acid has been detected in multiple biofluids, such as saliva, urine, and blood. Within the cell, levulinic acid is primarily located in the cytoplasm. Levulinic acid can be converted into 5-aminolevulinic acid. Levulinic acid is a sweet, acetoin, and acidic tasting compound that can be found in a number of food items such as alcoholic beverages, cereals and cereal products, fruits, and green vegetables. This makes levulinic acid a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
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
LevulinateGenerator
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
4-OxopentanoateHMDB
4-Oxopentanoic acidHMDB
DiasporalMeSH
Levulinic acid, sodium saltMeSH
Magnesium diasporalMeSH
Calcium levulateMeSH
Magnesium levulinateMeSH
Calcium levulinateMeSH
Levulinic acid, ammonium saltMeSH
Levulinic acid, calcium saltMeSH
Magnesium laevulinateMeSH
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name4-oxopentanoic acid
Traditional Namelevulinic acid
CAS Registry Number123-76-2
SMILES
CC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyJOOXCMJARBKPKM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 - 33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.49HANSCH,C ET AL. (1995)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ug0-6900000000-ffad5af79457e68cca02View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-dd0d17209893b2b71d10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-0b0447e3daa65b1cd932View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e0d39a4a978220036faaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-6900000000-ffad5af79457e68cca02View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-beecc1bba7b8b0ca4201View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9500000000-8c1e2090296fa71bf0d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00xr-9400000000-923a1fccce36ba18d088View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01vo-9300000000-2c09d37e792efac90655View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0303-9800000000-d158f0c32e82eca0ef90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-dd0d17209893b2b71d10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-9400000000-1043277f0ad49a5664a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9100000000-0a0fca12836c8c8ba113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-247961be84518f0ebcdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-b8133a0e2c97f98cef46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9600000000-e133b145c780f2c290d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9000000000-6ff5c46cdc591b725694View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified6.691 +/- 5.255 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified0.87 (0.31-1.92) umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified1.3 (0.4-2.0) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified1.28 (0.33-2.75) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified1.7 (0.6-2.5) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected and Quantified8.873 +/- 7.994 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified414.784 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDDB02239
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB003296
    KNApSAcK IDNot Available
    Chemspider ID11091
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkLevulinic_acid
    METLIN ID2195
    PubChem Compound11579
    PDB IDSHF
    ChEBI ID45630
    References
    Synthesis ReferenceCai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong. Review on preparation methods of levulinic acid, a new platform chemical. Xiandai Huagong (2003), 23(4), 14-16.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
    2. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
    3. Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome]. Nefrologia. 2004;24 Suppl 3:85-8. [PubMed:15219077 ]
    4. Melgaard B, Clausen J, Rastogi SC: Heavy metal levels and delta-amino-levulinic acid dehydrase levels in peripheral polyneuropathy. Acta Neurol Scand. 1976 Apr;53(4):291-307. [PubMed:178141 ]
    5. Matsui M, Kaji R, Oka N, Nishio T, Kimura J: [Multifocal axonal motor neuropathy associated with anti-ganglioside antibodies]. Rinsho Shinkeigaku. 1992 Oct;32(10):1130-5. [PubMed:1297559 ]
    6. Keithly L, Ferris Wayne G, Cullen DM, Connolly GN: Industry research on the use and effects of levulinic acid: a case study in cigarette additives. Nicotine Tob Res. 2005 Oct;7(5):761-71. [PubMed:16191747 ]
    7. Endo G, Horiguchi S, Kiyota I: Urinary N-acetyl-beta-D-glucosaminidase activity in lead-exposed workers. J Appl Toxicol. 1990 Aug;10(4):235-8. [PubMed:2391405 ]