PYRUVALDEHYDE (CED0007599)

Record Information
Version1.0
Creation Date2016-05-19 02:24:51 UTC
Update Date2026-05-14 17:50:45 UTC
Accession NumberCHEM007381
Identification
Common NamePYRUVALDEHYDE
ClassSmall Molecule
Description
PYRUVALDEHYDE (C3H4O2) is an organic oxygen compound with an average molecular weight of 72.06 g/mol. PYRUVALDEHYDE belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. It is utilized industrially as a nutrient and a flavouring agent. The compound is found in or released from 28 recorded sources. These include drinking water, as well as food, food processing, and cookware sources such as food contact materials, the preparation of vinegar, the preparation of malt, fermentation processes for beer, and food preservation. In household cleaning and consumer products, it is associated with soap detergents, bleaching agents, perfumes within detergents and soaps, cigar cigarettes, and other smoking requisites. It is also found in electrical and electronic equipment, including antennas, amplifiers, electric switches, conductors or conductive bodies characterised by the conductive materials, and cores yokes or armatures. Recorded exposure routes for the compound include touch, oral, and inhalation. PYRUVALDEHYDE has two recorded protein targets: Transient receptor potential cation channel subfamily A member 1 (TRPA1) and Phospholipase A2 (PLA2G1B), for which it acts as an activator or inhibitor. Regarding health effects, the compound serves as a biomarker of cancer (PMC13407726). Additionally, blood levels of PYRUVALDEHYDE are increased in instances of hyperglycemia (PMC9572970) and inflammation (PMC9572970).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1,2-PropanedioneChEBI
2-KetopropionaldehydeChEBI
2-OxopropanalChEBI
2-OxopropionaldehydeChEBI
AcetylformaldehydeChEBI
AcetylformylChEBI
alpha-KetopropionaldehydeChEBI
CH3COCHOChEBI
Pyruvic aldehydeChEBI
a-KetopropionaldehydeGenerator
Α-ketopropionaldehydeGenerator
Aldehyde, pyruvicMeSH
OxopropanalMeSH
1-KetopropionaldehydeHMDB
2-keto PropionaldehydeHMDB
2-oxo-PropionaldehydeHMDB
KetopropionaldehydeHMDB
MethylglyoxalHMDB
PropanedioneHMDB
PropanoloneHMDB
Pyroracemic aldehydeHMDB
Chemical FormulaC3H4O2
Average Molecular Mass72.063 g/mol
Monoisotopic Mass72.021 g/mol
CAS Registry Number78-98-8
IUPAC Name2-oxopropanal
Traditional Namemethylglyoxal
SMILESCC(=O)C=O
InChI IdentifierInChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
InChI KeyAIJULSRZWUXGPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha ketoaldehydes
Alternative Parents
Substituents
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • 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 Solubility180 g/LALOGPS
logP-0.38ALOGPS
logP0.2ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)16.38ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.05 m³·mol⁻¹ChemAxon
Polarizability6.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9000000000-43f9b3c94058c64733b5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-9000000000-964129275940a60a617dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006y-9000000000-0ae1e5fd2d50b28f967cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-9000000000-964129275940a60a617dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-110d6fcd891f2c54a2cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-9000000000-bec3651f9ea6825cf4f7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-8db5b1ba128748e220c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-f968a2358e6fd85ae268Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-0797bdeaa575b54943c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-9000000000-89ef1c082b2ef672eb67Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-5b936b9153956c2f64beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-9190b139940adf0d92c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-570ca33f905cecb028a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-482389dce4f05675f174Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-79267be0bc618dc8018fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-87bbaed151efac084591Not 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
953.0Log mg/kg[540:1700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationelevated_in_blood_inincreasePMC9572970
canceris_biomarker_ofNot AvailablePMC13407726
hyperglycemiaelevated_in_blood_inincreasePMC9572970
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & 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
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, 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
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
24 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureComplement factor DP32038Rattus norvegicusPredicted (SEA)129.93
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)4430.87
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)10.821
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)5758.66
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)4585.63
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)5098.73
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)5366.69
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseQ9WVM4Rattus norvegicusPredicted (SEA)5.83869
Hydroxycarboxylic acid receptor 2 structureClick to view 3D structureHydroxycarboxylic acid receptor 2Q8TDS4HumansPredicted (SEA)403.726
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseP32584Saccharomyces cerevisiae S288cPredicted (SEA)7.31783
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)4241.85
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)2894.67
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)734.663
Click to view 3D structureHistidine biosynthesis bifunctional protein HisBP06987Escherichia coli O26:H11 str. CFSAN001629Predicted (SEA)42.0386
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)4526.31
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)5296.55
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)7095.72
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)7112.07
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)4911.51
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)3714.11
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)279.712
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)6175.08
Nuclear factor erythroid 2-related factor 2 structureClick to view 3D structureNuclear factor erythroid 2-related factor 2Q16236HumansPredicted (SEA)740.113
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)4877.88
Click to view 3D structureCarbonic anhydraseQ2PCB5Dicentrarchus labraxPredicted (SEA)171.58
Concentrations
Not Available
External Links
DrugBank IDDB03587
HMDB IDHMDB0001167
FooDB IDFDB008295
Phenol Explorer IDNot Available
KNApSAcK IDC00007562
BiGG ID35307
BioCyc IDMETHYL-GLYOXAL
METLIN ID6049
PDB IDNot Available
Wikipedia LinkMethylglyoxal
Chemspider ID857
ChEBI ID17158
PubChem Compound ID880
Kegg Compound IDC00546
YMDB IDYMDB00170
ECMDB IDECMDB01167
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.
2. Wondrak GT, Cervantes-Laurean D, Roberts MJ, Qasem JG, Kim M, Jacobson EL, Jacobson MK: Identification of alpha-dicarbonyl scavengers for cellular protection against carbonyl stress. Biochem Pharmacol. 2002 Feb 1;63(3):361-73.
3. Mottaran E, Stewart SF, Rolla R, Vay D, Cipriani V, Moretti M, Vidali M, Sartori M, Rigamonti C, Day CP, Albano E: Lipid peroxidation contributes to immune reactions associated with alcoholic liver disease. Free Radic Biol Med. 2002 Jan 1;32(1):38-45.
4. Lo TW, Selwood T, Thornalley PJ: The reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins. Biochem Pharmacol. 1994 Nov 16;48(10):1865-70.
5. Gildersleeve DL, Tobes MC, Natale RB: Rapid analysis for methylglyoxal bis(guanylhydrazone) by reversed-phase ion-pair liquid chromatography. Clin Chem. 1985 Dec;31(12):1979-84.
6. Ahmed N, Thornalley PJ, Dawczynski J, Franke S, Strobel J, Stein G, Haik GM: Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins. Invest Ophthalmol Vis Sci. 2003 Dec;44(12):5287-92.
7. Seppanen P, Alhonen-Hongisto L, Janne J: Polyamine deprivation-induced enhanced uptake of methylglyoxal bis(guanylhydrazone) by tumor cells. Biochim Biophys Acta. 1981 May 5;674(2):169-77.
8. Ahmed MU, Brinkmann Frye E, Degenhardt TP, Thorpe SR, Baynes JW: N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem J. 1997 Jun 1;324 ( Pt 2):565-70.
9. Riley ML, Harding JJ: The reaction of methylglyoxal with human and bovine lens proteins. Biochim Biophys Acta. 1995 Jan 25;1270(1):36-43.
10. Beisswenger PJ, Drummond KS, Nelson RG, Howell SK, Szwergold BS, Mauer M: Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov;54(11):3274-81.
11. Nemet I, Varga-Defterdarovic L, Turk Z: Preparation and quantification of methylglyoxal in human plasma using reverse-phase high-performance liquid chromatography. Clin Biochem. 2004 Oct;37(10):875-81.
12. Thornalley PJ, Argirova M, Ahmed N, Mann VM, Argirov O, Dawnay A: Mass spectrometric monitoring of albumin in uremia. Kidney Int. 2000 Nov;58(5):2228-34.
13. Baskaran S, Rajan DP, Balasubramanian KA: Formation of methylglyoxal by bacteria isolated from human faeces. J Med Microbiol. 1989 Mar;28(3):211-5.
14. Kuhla B, Luth HJ, Haferburg D, Boeck K, Arendt T, Munch G: Methylglyoxal, glyoxal, and their detoxification in Alzheimer's disease. Ann N Y Acad Sci. 2005 Jun;1043:211-6.
15. Schupp N, Schinzel R, Heidland A, Stopper H: Genotoxicity of advanced glycation end products: involvement of oxidative stress and of angiotensin II type 1 receptors. Ann N Y Acad Sci. 2005 Jun;1043:685-95.
16. Haik GM Jr, Lo TW, Thornalley PJ: Methylglyoxal concentration and glyoxalase activities in the human lens. Exp Eye Res. 1994 Oct;59(4):497-500.
17. Shamsi FA, Lin K, Sady C, Nagaraj RH: Methylglyoxal-derived modifications in lens aging and cataract formation. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2355-64.
18. Jan CR, Chen CH, Wang SC, Kuo SY: Effect of methylglyoxal on intracellular calcium levels and viability in renal tubular cells. Cell Signal. 2005 Jul;17(7):847-55. Epub 2004 Dec 8.
19. Ahmed N, Dobler D, Dean M, Thornalley PJ: Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem. 2005 Feb 18;280(7):5724-32. Epub 2004 Nov 22.
20. Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.
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28. https://www.ncbi.nlm.nih.gov/pubmed/?term=22983866
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