Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:59 UTC |
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Update date | 2020-09-17 15:38:20 UTC |
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Primary ID | FDB001478 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Glyoxylic acid |
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Description | Glyoxylic 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. |
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CAS Number | 298-12-4 |
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Structure | |
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Synonyms | Synonym | Source |
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alpha-Ketoacetic acid | ChEBI | Formylformic acid | ChEBI | Glyoxalate | ChEBI | Glyoxalsaeure | ChEBI | Glyoxylate | ChEBI | Glyoxylsaeure | ChEBI | Oxalaldehydic acid | ChEBI | Oxoethanoic acid | ChEBI | a-Ketoacetate | Generator | a-Ketoacetic acid | Generator | alpha-Ketoacetate | Generator | Α-ketoacetate | Generator | Α-ketoacetic acid | Generator | Formylformate | Generator | Glyoxalic acid | Generator | Oxalaldehydate | Generator | Oxoethanoate | Generator | Oxoacetate | HMDB | Oxoacetic acid | HMDB | Glyoxylic acid, 2-(14)C-labeled | HMDB | Glyoxylic acid, sodium salt | HMDB | Glyoxylic acid, sodium salt, 2-(14)C-labeled | HMDB | Glyoxylic acid, 14c2-labeled | HMDB | Glyoxylic acid, calcium salt | HMDB | Glyoxylic acid, sodium salt, 14C-labeled | HMDB | α-Ketoacetic acid | biospider | Acetic acid, 2-oxo- | biospider | Acetic acid, oxo- (9CI) | biospider | Glyoxylic acid (8CI) | biospider | Oxaldehydic acid | biospider | α-ketoacetate | Generator | α-ketoacetic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C2H2O3 |
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IUPAC name | 2-oxoacetic acid |
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InChI Identifier | InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) |
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InChI Key | HHLFWLYXYJOTON-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)C=O |
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Average Molecular Weight | 74.0355 |
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Monoisotopic Molecular Weight | 74.00039393 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acids |
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Direct Parent | Carboxylic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | V. deliquescent prisms giving yellow aq. soln. | CCD |
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Mass Composition | C 32.45%; H 2.72%; O 64.83% | CCD |
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Melting Point | Mp 104 - 107° (sinters from 94°) | CCD |
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Boiling Point | Not Available | |
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Experimental Water Solubility | V. sol. H2O; spar. sol. EtOH, Et2O | CCD |
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Experimental logP | Not Available | |
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Experimental pKa | p Ka2.32 | CCD |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-004l-9000000000-a04bafbf8e0b990094a3 | 2014-09-20 | View Spectrum | GC-MS | Glyoxylic acid, 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-03di-3900000000-16bc69e0e9d51e54854e | Spectrum | GC-MS | Glyoxylic acid, non-derivatized, GC-MS Spectrum | splash10-03di-3900000000-16bc69e0e9d51e54854e | Spectrum | Predicted GC-MS | Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0096-9000000000-042540a05be250278f8b | Spectrum | Predicted GC-MS | Glyoxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00fr-9200000000-c60b627ed670285ec37f | Spectrum | Predicted GC-MS | Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glyoxylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-9000000000-72c34bc34b8c3341442b | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9000000000-920a0dc738957201d4ba | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00di-9000000000-857c7f2d72c3d4c10dbf | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-9000000000-9b5825d5d9d8b094fefa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-9000000000-de556f03ea428deff5e2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00dl-9000000000-74b253632894213d473c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-9b5825d5d9d8b094fefa | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-de556f03ea428deff5e2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00dl-9000000000-74b253632894213d473c | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-a8cc2c89793394fdf9e4 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-9000000000-d20183b08984d4766e8a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-ea9968e3933fd734506c | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-cef8efc477a2500a7ead | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-3817c0865df629803538 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-bb935f857fb5fd08c7e3 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-9000000000-8f50f0d32d4c40b5b935 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-b6216caa16afdf328489 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-aa6a654e73df38a43273 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-c6f38ec60bcf8724ecd1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-c6f38ec60bcf8724ecd1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dl-9000000000-641421c616a0929ce01e | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 740 |
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ChEMBL ID | CHEMBL1162545 |
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KEGG Compound ID | C00048 |
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Pubchem Compound ID | 760 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16891 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB04343 |
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HMDB ID | HMDB00119 |
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CRC / DFC (Dictionary of Food Compounds) ID | CVS76-X:CVS76-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | GLYOXYLIC-ACID|GLYOXALIC-ACID |
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BIGG ID | 33659 |
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KNApSAcK ID | C00001186 |
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HET ID | GLV |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Glyoxylic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Alanine--glyoxylate aminotransferase 2, mitochondrial | AGXT2 | Q9BYV1 | Kynurenine--oxoglutarate transaminase 3 | CCBL2 | Q6YP21 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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).
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