Either of two isomers with the formula HCOOHC=CHCOOH. Both compounds can be regarded as derivatives of ethene in which a hydrogen atom on each carbon has been replaced by a –COOH group. The compounds show cis-trans isomerism. The trans form is fumaric acid (r.d. 1.64; sublimes at 165°C) and the cis form is maleic acid (r.d. 1.59; m.p. 139–140°C). Both are colourless crystalline compounds used in making synthetic resins. The cis form is rather less stable than the trans form and converts to the trans form at 120°C. Unlike the trans form it can eliminate water on heating to form a cyclic anhydride containing a –CO.O.CO– group (maleic anhydride). Fumaric acid is an intermediate in the Krebs cycle.
Butenedioic acid
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