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
α-Ketoacetic acidbiospider
a-Ketoacetatebiospider
a-Ketoacetic acidbiospider
Acetic acid, 2-oxo-biospider
Acetic acid, oxo- (9CI)biospider
alpha-Ketoacetatebiospider
alpha-Ketoacetic acidbiospider
Formylformatebiospider
Formylformic acidbiospider
Glyoxalatebiospider
Glyoxalic acidbiospider
GlyoxalsaeureChEBI
Glyoxylatebiospider
Glyoxylic acid (8CI)biospider
GlyoxylsaeureChEBI
Oxalaldehydatebiospider
Oxalaldehydic acidbiospider
Oxaldehydic acidbiospider
Oxoacetatebiospider
Oxoacetic acidbiospider
Oxoethanoatebiospider
Oxoethanoic 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
ClassificationNot classified
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-a04bafbf8e0b990094a32014-09-20View Spectrum
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
Predicted GC-MSGlyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlyoxylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9000000000-72c34bc34b8c3341442b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-920a0dc738957201d4ba2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-857c7f2d72c3d4c10dbf2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-9b5825d5d9d8b094fefa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-de556f03ea428deff5e22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9000000000-74b253632894213d473c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9b5825d5d9d8b094fefa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-de556f03ea428deff5e22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-74b253632894213d473c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-a8cc2c89793394fdf9e42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-d20183b08984d4766e8a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ea9968e3933fd734506c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cef8efc477a2500a7ead2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-3817c0865df6298035382015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bb935f857fb5fd08c7e32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-8f50f0d32d4c40b5b9352021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b6216caa16afdf3284892021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-aa6a654e73df38a432732021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-641421c616a0929ce01e2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).