Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2020-09-17 15:38:20 UTC
Primary IDFDB001478
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlyoxylic acid
DescriptionGlyoxylic acid, also known as a-ketoacetate or glyoxalate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom. Glyoxylic acid exists in all living species, ranging from bacteria to humans. L-alanine and glyoxylic acid can be biosynthesized from glycine and pyruvic acid through its interaction with the enzyme serine--pyruvate aminotransferase. In humans, glyoxylic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Glyoxylic acid has been detected, but not quantified in, tamarinds. This could make glyoxylic acid a potential biomarker for the consumption of these foods. Glyoxylic acid is a potentially toxic compound. Glyoxylic acid, with regard to humans, has been found to be associated with several diseases such as bladder infections and transurethral resection of the prostate; glyoxylic acid has also been linked to the inborn metabolic disorder primary hyperoxaluria I.
CAS Number298-12-4
Structure
Thumb
Synonyms
SynonymSource
alpha-Ketoacetic acidChEBI
Formylformic acidChEBI
GlyoxalateChEBI
GlyoxalsaeureChEBI
GlyoxylateChEBI
GlyoxylsaeureChEBI
Oxalaldehydic acidChEBI
Oxoethanoic acidChEBI
a-KetoacetateGenerator
a-Ketoacetic acidGenerator
alpha-KetoacetateGenerator
Α-ketoacetateGenerator
Α-ketoacetic acidGenerator
FormylformateGenerator
Glyoxalic acidGenerator
OxalaldehydateGenerator
OxoethanoateGenerator
OxoacetateHMDB
Oxoacetic acidHMDB
Glyoxylic acid, 2-(14)C-labeledHMDB
Glyoxylic acid, sodium saltHMDB
Glyoxylic acid, sodium salt, 2-(14)C-labeledHMDB
Glyoxylic acid, 14c2-labeledHMDB
Glyoxylic acid, calcium saltHMDB
Glyoxylic acid, sodium salt, 14C-labeledHMDB
α-Ketoacetic acidbiospider
Acetic acid, 2-oxo-biospider
Acetic acid, oxo- (9CI)biospider
Glyoxylic acid (8CI)biospider
Oxaldehydic acidbiospider
α-ketoacetateGenerator
α-ketoacetic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility224 g/LALOGPS
logP-0.59ALOGPS
logP-0.13ChemAxon
logS0.48ALOGPS
pKa (Strongest Acidic)2.61ChemAxon
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.5 m³·mol⁻¹ChemAxon
Polarizability5.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H2O3
IUPAC name2-oxoacetic acid
InChI IdentifierInChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
InChI KeyHHLFWLYXYJOTON-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C=O
Average Molecular Weight74.0355
Monoisotopic Molecular Weight74.00039393
Classification
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionV. deliquescent prisms giving yellow aq. soln.CCD
Mass CompositionC 32.45%; H 2.72%; O 64.83%CCD
Melting PointMp 104 - 107° (sinters from 94°)CCD
Boiling PointNot Available
Experimental Water SolubilityV. sol. H2O; spar. sol. EtOH, Et2OCCD
Experimental logPNot Available
Experimental pKap Ka2.32CCD
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-a04bafbf8e0b990094a3Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MSGlyoxylic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-03di-3900000000-16bc69e0e9d51e54854eSpectrum
GC-MSGlyoxylic acid, non-derivatized, GC-MS Spectrumsplash10-03di-3900000000-16bc69e0e9d51e54854eSpectrum
Predicted GC-MSGlyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0096-9000000000-042540a05be250278f8bSpectrum
Predicted GC-MSGlyoxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9200000000-c60b627ed670285ec37fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9000000000-72c34bc34b8c3341442bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-920a0dc738957201d4baSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-857c7f2d72c3d4c10dbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-de556f03ea428deff5e2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9000000000-74b253632894213d473cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-de556f03ea428deff5e2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-74b253632894213d473cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-a8cc2c89793394fdf9e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-d20183b08984d4766e8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ea9968e3933fd734506cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cef8efc477a2500a7eadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-3817c0865df629803538Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bb935f857fb5fd08c7e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-8f50f0d32d4c40b5b935Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b6216caa16afdf328489Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-aa6a654e73df38a43273Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-c6f38ec60bcf8724ecd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-641421c616a0929ce01eSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID740
ChEMBL IDCHEMBL1162545
KEGG Compound IDC00048
Pubchem Compound ID760
Pubchem Substance IDNot Available
ChEBI ID16891
Phenol-Explorer IDNot Available
DrugBank IDDB04343
HMDB IDHMDB00119
CRC / DFC (Dictionary of Food Compounds) IDCVS76-X:CVS76-X
EAFUS IDNot Available
Dr. Duke IDGLYOXYLIC-ACID|GLYOXALIC-ACID
BIGG ID33659
KNApSAcK IDC00001186
HET IDGLV
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlyoxylic 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 / Bioactivities
DescriptorIDDefinitionReference
irritantDUKE
Enzymes
NameGene NameUniProt ID
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Glycine and Serine MetabolismSMP00004 map00260
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).