Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000281
Name: Pyruvaldehyde
Description:Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.
  • 1,2-Propanedione
  • 1-Ketopropionaldehyde
  • 2-Keto Propionaldehyde
  • 2-Ketopropionaldehyde
  • 2-Oxo-propanal
  • 2-Oxo-Propionaldehyde
  • 2-Oxopropanal
  • a-Ketopropionaldehyde
  • Acetylformaldehyde
  • Acetylformyl
  • Alpha-Ketopropionaldehyde
  • Ketopropionaldehyde
  • Methyl-glyoxal
  • Methylglyoxal
  • Oxopropanal
  • Propanedione
  • Propanolone
  • Pyroracemic aldehyde
  • Pyruvaldehyde
  • Pyruvic aldehyde
  • α-Ketopropionaldehyde
Chemical Formula: C3H4O2
Average Molecular Weight: 72.0627
Monoisotopic Molecular Weight: 72.021129372
CAS number: 78-98-8
IUPAC Name:2-oxopropanal
Traditional IUPAC Name: methylglyoxal
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbonyl compounds
Sub ClassAldehydes
Direct Parent Alpha ketoaldehydes
Alternative Parents
  • Alpha-ketoaldehyde
  • Ketone
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Melting point: < 25 °C
Experimental Properties:
Predicted Properties
Water Solubility180.0 mg/mLALOGPS
pKa (Strongest Acidic)16.38ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.05 m3·mol-1ChemAxon
Polarizability6.42 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dj-9000000000-964129275940a60a617dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006y-9000000000-0ae1e5fd2d50b28f967cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dj-9000000000-964129275940a60a617dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-110d6fcd891f2c54a2cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-bec3651f9ea6825cf4f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8db5b1ba128748e220c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-f968a2358e6fd85ae268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-0797bdeaa575b54943c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-89ef1c082b2ef672eb67View in MoNA
  • 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. Pubmed: 9182719
  • 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. Pubmed: 15557329
  • 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. Pubmed: 14638728
  • Baskaran S, Rajan DP, Balasubramanian KA: Formation of methylglyoxal by bacteria isolated from human faeces. J Med Microbiol. 1989 Mar;28(3):211-5. Pubmed: 2926792
  • 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. Pubmed: 16249455
  • 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. Pubmed: 4064286
  • 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. Pubmed: 7859825
  • 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. Pubmed: 15763427
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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. Pubmed: 16037241
  • 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. Pubmed: 7986197
  • 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. Pubmed: 11755315
  • 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. Pubmed: 15369718
  • Riley ML, Harding JJ: The reaction of methylglyoxal with human and bovine lens proteins. Biochim Biophys Acta. 1995 Jan 25;1270(1):36-43. Pubmed: 7827133
  • 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. Pubmed: 16037294
  • 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. Pubmed: 6786360
  • 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. Pubmed: 9804144
  • 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. Pubmed: 11044246
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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. Pubmed: 11853687
Synthesis Reference: Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.
Material Safety Data Sheet (MSDS) Download (PDF)
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Pubchem Compound ID880
Kegg IDC00546
ChemSpider ID857
Ligand ExpoPVL