LEVULINIC ACID (CED0004560)

Record Information
Version1.0
Creation Date2016-05-19 02:12:13 UTC
Update Date2026-05-14 17:31:59 UTC
Accession NumberCHEM006300
Identification
Common NameLEVULINIC ACID
ClassSmall Molecule
Description
LEVULINIC ACID (C5H8O3) is an organic compound with an average molecular weight of 116.12 g/mol. LEVULINIC ACID belongs to the gamma-keto acids and derivatives, a subclass of keto acids and derivatives within the organic compounds. In industrial applications, it is used as a solvent (PMC11639324), a surfactant, a fragrance, a softener and conditioner, and as a nutrient and flavouring (PMC10857383). Additionally, the compound is used in the production of Polyamide plastics. The compound is found in or released from 34 recorded sources. These include household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with food, food processing and cookware, specifically food contact materials, food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer. Other sources include building and construction materials like ceilings and floors, household items such as coins, and electrical and electronic equipment including amplifiers, antennas, conductors or conductive bodies characterised by the conductive materials, electric switches, and electrically stimulated smoking devices. Recorded exposure routes for this compound include oral, inhalation, and touch. Regarding its biological activity, LEVULINIC ACID is a recorded inhibitor of the protein target Delta-aminolevulinic acid dehydratase (ALAD).
Contaminant TypeNot Available
Chemical Structure
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
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
Chemical FormulaC5H8O3
Average Molecular Mass116.115 g/mol
Monoisotopic Mass116.047 g/mol
CAS Registry Number123-76-2
IUPAC Name4-oxopentanoic acid
Traditional Namelevulinic acid
SMILESCC(=O)CCC(O)=O
InChI IdentifierInChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyJOOXCMJARBKPKM-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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0ug0-6900000000-1e5d9b8d9a359287a6b0Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0ug0-6900000000-ffad5af79457e68cca02Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-9000000000-dd0d17209893b2b71d10Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-9000000000-0b0447e3daa65b1cd932Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-9000000000-e0d39a4a978220036faaNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0ug0-6900000000-1e5d9b8d9a359287a6b0Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0ug0-6900000000-ffad5af79457e68cca02Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9000000000-beecc1bba7b8b0ca4201Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00fr-9500000000-8c1e2090296fa71bf0d0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-9400000000-923a1fccce36ba18d088Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01vo-9300000000-2c09d37e792efac90655Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0303-9800000000-d158f0c32e82eca0ef90Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-dd0d17209893b2b71d10Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006x-9000000000-adbd744553b432e3c700Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-469fd98086c8d9ad1830Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9200000000-e73b5a48710de1cc7a5dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-9400000000-1043277f0ad49a5664a3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-9100000000-0a0fca12836c8c8ba113Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-9000000000-247961be84518f0ebcdaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3900000000-b8133a0e2c97f98cef46Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-9600000000-e133b145c780f2c290d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052e-9000000000-6ff5c46cdc591b725694Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xs-9300000000-eb059cdb2e36fd93dd56Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-9000000000-1e533a2764dd57c91302Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-c7b0e35a1f31ca5d7853Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ea-9000000000-8e96196fb7b3bcd96a40Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-a8096e58fd006cbfe211Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-83517d34c408e5f9d048Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2042.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
571CoinsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)0.622794
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)0.0778492
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)6.85073
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)0.155698
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)19.3845
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)28.7264
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)2.64687
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)27.3251
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)69.9865
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)12.6894
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)0.389246
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)44.4519
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)110.546
Click to view 3D structureN-acetylaspartylglutamate synthase AQ8IXN7HumansPredicted (SEA)6.46149
Gamma-glutamyl hydrolase structureClick to view 3D structureGamma-glutamyl hydrolaseQ92820HumansPredicted (SEA)3.34752
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)11.2881
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)9.57545
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)70.6871
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)1.08989
Lysine-specific demethylase 4E structureClick to view 3D structureLysine-specific demethylase 4EB2RXH2HumansPredicted (SEA)52.0811
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)6.07224
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseP32584Saccharomyces cerevisiae S288cPredicted (SEA)1.86838
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)60.2553
Click to view 3D structureSodium- and chloride-dependent creatine transporter 1P48029HumansPredicted (SEA)0.622794
Concentrations
Not Available
External Links
DrugBank IDDB02239
HMDB IDHMDB0000720
FooDB IDFDB003296
Phenol Explorer IDNot Available
KNApSAcK IDC00051252
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2195
PDB IDNot Available
Wikipedia LinkLevulinic_acid
Chemspider ID11091
ChEBI ID45630
PubChem Compound ID11579
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB21398
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13215009
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16662002
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19246769
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23627123
5. Cai, 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.
6. Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome]. Nefrologia. 2004;24 Suppl 3:85-8.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.