Maleamic acid

Maleamic acid

File:MaleamicAcid.svg
Identifiers
CAS Number	557-24-4 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29045
ChemSpider	4444106
ECHA InfoCard
EC Number	209-163-4
E number
KEGG	C01596
PubChem CID	5280451
UNII	MJS1DTX3X1
CompTox Dashboard (EPA)	{{#property:P3117}}
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	GHS07: Exclamation mark
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. 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.

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).