Chemistry:Oxamic acid
From HandWiki
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 Ball and stick model of oxamic acid
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| Names | |
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| 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 | |
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3D model (JSmol)
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| Properties | |
| NH 2C(O)COOH | |
| Molar mass | 89.050 g·mol−1 |
| Appearance | White solid |
| Melting point | 209 °C[2] |
| Soluble | |
| Acidity (pKa) | 1.8[3] |
| Hazards | |
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P271, P280, P302+352, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Oxamic acid is an organic compound with the formula NH
2C(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
- Oxamate, the conjugate base of oxamic acid
References
- ↑ 1.0 1.1 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.
- ↑ CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. 2011. p. 3.430. ISBN 978-1-4398-5511-9. https://archive.org/details/crchandbookofche00davi.
- ↑ 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. https://www.sciencedirect.com/science/article/abs/pii/S0020169300933437.
- ↑ "Oxamic acid". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/oxamic_acid#section=Depositor-Supplied-Synonyms.
- ↑ "Synergistic anti-cancer effect of phenformin and oxamate". PLOS ONE 9 (1). 2014. doi:10.1371/journal.pone.0085576. PMID 24465604. Bibcode: 2014PLoSO...985576M.
- ↑ 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. doi:10.1002/app.28609. ISSN 0021-8995. Bibcode: 2008JAPS..110...66Z.
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