Oxamic acid

Oxamic acid
	; Ball and stick model of oxamic acid
Names
	Preferred IUPAC name Oxamic acid[1]
	Systematic IUPAC name 2-Amino-2-oxoethanoic acid
	Other names Amino(oxo)acetic acid[1]; 2-Amino-2-oxoacetic acid; Aminooxoacetic acid; Oxalamic acid; Oxamidic acid
Identifiers
CAS Number	471-47-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	949;
ECHA InfoCard	100.006.768
PubChem CID	974;
UNII	QU60N5OPLG ;
CompTox Dashboard (EPA)	DTXSID6060052 ;
	SMILES C(=O)(C(=O)O)N;
Properties
Chemical formula	C2H3NO3
Molar mass	89.050 g·mol−1
Appearance	white solid
Melting point	209 °C[2]
	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 the organic compound with the formula H₂NC(O)CO₂H. It is a white, water-soluble solid. It is the monoamide of oxalic acid.[3] Oxamic acid inhibits Lactate dehydrogenase A.[4] The active site of lactate dehydrogenase (LDH) is closed off once oxamic acid attaches to the LDH-NADH complex, effectively inhibiting it.[5]

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[6].

References

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.
"Oxamic acid". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. 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. 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. doi:10.1002/app.28609. ISSN 0021-8995.

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[iupac2013-1] 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.

[2] 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.

[3] "Oxamic acid". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2016-12-14.

[4] 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. doi:10.1371/journal.pone.0085576. PMC 3897486. PMID 24465604.

[5] 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.

[6] 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.