Oxamic acid
(Redirected from C2H3NO3)
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 Ball and stick model of oxamic acid | |
| Names | |
|---|---|
| Preferred IUPAC name
Oxamic acid[1] | |
| Other names
Amino(oxo)acetic acid[1] 2-Amino-2-oxoacetic acid 2-oxoglycine Aminooxoacetic acid Oxalamic acid Oxamidic acid 2-Amino-2-oxoethanoic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.006.768 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| NH2C(O)COOH | |
| Molar mass | 89.050 g·mol−1 |
| Appearance | White solid |
| Melting point | 209 °C[2] |
| Soluble | |
| Acidity (pKa) | 1.8[3] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxamic acid is an organic compound with the formula NH2C(O)COOH. It is a white, water-soluble solid. It is the monoamide of oxalic acid.[4] Oxamic acid inhibits lactate dehydrogenase A.[5] The active site of lactate dehydrogenase (LDH) is closed off once oxamic acid attaches to the LDH-NADH complex, effectively inhibiting it.[6]
Oxamic acid also has applications in polymer chemistry. It increases the water solubility of certain polymers, including polyester, epoxide, and acrylic upon binding with them.[7]
See also
[edit]- Oxamate, the conjugate base of oxamic acid
References
[edit]- 1 2 Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 415. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ↑ Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 3.430. ISBN 978-1-4398-5511-9.
- ↑ Braibanti, A.; Leporati, E.; Dallavalle, F. (11 August 1970). "The protonation constant of oxamic acid in aqueous solution and in water-tetrahydrofuran mixture, at different temperatures and ionic strengths". Inorg. Chim. Acta. 4: 529–532. doi:10.1016/S0020-1693(00)93343-7.
- ↑ "Oxamic acid". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Archived from the original on 2016-12-01. Retrieved 2016-12-14.
- ↑ Miskimins WK, Ahn HJ, Kim JY, Ryu S, Jung YS, Choi JY (2014). "Synergistic anti-cancer effect of phenformin and oxamate". PLOS ONE. 9 (1) e85576. Bibcode:2014PLoSO...985576M. doi:10.1371/journal.pone.0085576. PMC 3897486. PMID 24465604.
- ↑ Raczyńska, Ewa D.; Hallmann, Małgorzata; Duczmal, Kinga (March 2011). "Quantum-chemical studies of amide–iminol tautomerism for inhibitor of lactate dehydrogenase: Oxamic acid". Computational and Theoretical Chemistry. 964 (1–3): 310–317. doi:10.1016/j.comptc.2011.01.017. ISSN 2210-271X.
- ↑ Zarzyka-Niemiec, Iwona (2008-10-05). "Hydroxyalkylation of oxamic acid with propylene carbonate: Synthesis, composition, and properties of products". Journal of Applied Polymer Science. 110 (1): 66–75. Bibcode:2008JAPS..110...66Z. doi:10.1002/app.28609. ISSN 0021-8995.
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