Maleamic acid

Maleamic acid

Identifiers
CAS Number	557-24-4  Y
ECHA InfoCard	100.008.332
PubChem CID	5280451
CompTox Dashboard (EPA)	DTXSID301031738
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)
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

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.