Maleamic acid

Maleamic acid
Identifiers
CAS Number	557-24-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29045;
ChemSpider	4444106;
ECHA InfoCard	100.008.332
EC Number	209-163-4;
KEGG	C01596;
PubChem CID	5280451;
UNII	MJS1DTX3X1;
CompTox Dashboard (EPA)	DTXSID301031738 ;
	InChI InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1- Key: FSQQTNAZHBEJLS-UPHRSURJSA-N;
	SMILES C(=C\C(=O)O)\C(=O)N;
Properties
Chemical formula	C4H5NO3
Molar mass	115.088 g·mol−1
Appearance	white solid
Melting point	158–161 °C (316–322 °F; 431–434 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

Maleamic acid is an organic compound with the formula HO₂CCH=CHC(O)NH₂. It is the amide formed by reaction of maleic anhydride with ammonia. It is a colorless solid.^[1] Maleamic acid is the product of the action of the enzyme maleimide hydrolase.

Related compounds

A variety of maleamic acids are known. Commonly they are prepared by the reaction of an amine with maleic anhydride.^[2]

Aside from maleic anhydride, other common cyclic anhydrides (and imides) undergo ring-opening to give amido carboxylic acids. Succinic anhydride gives succinamic acid (HO₂CCH₂CH₂C(O)NH₂), citraconic anhydride gives two isomers of citraconamic acid (HO₂CCH₂CH(CH₃)C(O)NH₂ and HO₂CCH(CH₃)CH₂C(O)NH₂), and phthalimide gives phthalamidic acid (HO₂CC₆H₄C(O)NH₂).^[3]

References

^ Hood, David K. (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN 978-0-471-48494-3.
^ Mehta, Nariman B.; Phillips, Arthur P.; Lui, (MRS.) Florence FU; Brooks, Ronald E. (1960). "Maleamic and Citraconamic Acids, Methyl Esters, and Imides". The Journal of Organic Chemistry. 25 (6): 1012–1015. doi:10.1021/jo01076a038.
^ Hargreaves, Michael K.; Pritchard, J. G.; Dave, H. R. (1970). "Cyclic Carboxylic Monoimides". Chemical Reviews. 70 (4): 439–469. doi:10.1021/cr60266a001.

[1] Hood, David K. (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN 978-0-471-48494-3.

[2] Mehta, Nariman B.; Phillips, Arthur P.; Lui, (MRS.) Florence FU; Brooks, Ronald E. (1960). "Maleamic and Citraconamic Acids, Methyl Esters, and Imides". The Journal of Organic Chemistry. 25 (6): 1012–1015. doi:10.1021/jo01076a038.

[3] Hargreaves, Michael K.; Pritchard, J. G.; Dave, H. R. (1970). "Cyclic Carboxylic Monoimides". Chemical Reviews. 70 (4): 439–469. doi:10.1021/cr60266a001.

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