Record Information
Version1.0
Creation date2010-04-08 22:07:31 UTC
Update date2019-11-26 03:01:34 UTC
Primary IDFDB007244
Secondary Accession Numbers
  • FDB030895
  • FDB001478
Chemical Information
FooDB NameGlycoxylic acid
DescriptionGlyoxylic acid, also known as alpha-ketoacetic acid or glyoxylate, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Glyoxylic acid can be found in a number of food items such as european chestnut, cowpea, wheat, and common thyme, which makes glyoxylic acid a potential biomarker for the consumption of these food products. Glyoxylic acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout all human tissues. Glyoxylic acid exists in all living species, ranging from bacteria to humans. In humans, glyoxylic acid is involved in a couple of metabolic pathways, which include alanine metabolism and glycine and serine metabolism. Glyoxylic acid is also involved in several metabolic disorders, some of which include lactic acidemia, pyruvate carboxylase deficiency, 3-phosphoglycerate dehydrogenase deficiency, and hyperglycinemia, non-ketotic. Moreover, glyoxylic acid is found to be associated with transurethral resection of the prostate and primary hyperoxaluria I. Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially .
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
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
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
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-9000000000-72c34bc34b8c3341442bSpectrum
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 - 20V, 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
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGLYCOXYLIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).