Maleamic acid
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| ECHA InfoCard | 100.008.332 |
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| Properties | |
| C4H5NO3 | |
| Molar mass | 115.088 g·mol−1 |
| Appearance | white solid |
| Melting point | 158–161 °C (316–322 °F; 431–434 K) |
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| H315, H319, H335 | |
| 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).
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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]