4287. Fumaric Acid
Nomenclature
CAS number: 110-17-8
(2E)-2-Butenedioic acid; trans-1,2-ethylenedicarboxylic acid; allomaleic acid; boletic acid. C4H4O4; mol wt 116.07.
C 41.39%, H 3.47%, O 55.14%.
Description and references
Occurs in many plants, e.g., in Fumaria officinalis L., Fumariaceae, in Boletus scaber Bull., Boletaceae, and in Fomes igniarius (Fries) Kickx., Polyporaceae. Essential to vegetable and animal tissue respiration. Prepd industrially from glucose by the action of fungi such as Rhizopus nigricans: Foster, Waksman, J. Am. Chem. Soc. 61, 127 (1939). Laboratory prepn by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide: Milas, Org. Synth. coll. vol. II, 302 (1943). Molecular structure: J. L. Derissen, J. Mol. Struct. 38, 177 (1977). Review: W. D. Robinson, R. A. Mount in Kirk-Othmer Encyclopedia of Chemical Technology vol. 14 (Wiley-Interscience, New York, 3rd ed., 1981) pp 770-793.
Properties
Monoclinic, prismatic needles or leaflets from water. d 1.625. Sublimes at 200°. Sublimes at 165° at 1.7 mm pressure. Partial carbonization and formation of maleic anhydride occur at 230° (open vessel). mp 287° (closed capillary, rapid heating). pK1 (25°): 3.03; pK2: 4.54. Absorption spectrum: Macbeth, Stewart, J. Chem. Soc. 111, 830 (1917). Soly in 100 g water at 25°: 0.63 g; at 40°: 1.07 g; at 60°: 2.4 g; at 100°: 9.8 g; in 100 g 95% alcohol at 30°: 5.76 g; in 100 g acetone at 30°: 1.72 g; in 100 g ether at 25°: 0.72 g. Almost insol in olive oil, chloroform, carbon tetrachloride, benzene, xylene, molten camphor, liquid ammonia.Derivative
Monomethyl ester.C5H6O4; mol wt 130.10.
C 46.16%, H 4.65%, O 49.19%.
Properties
Prisms from alc, mp 144.5°.Derivative
Dimethyl ester.C6H8O4; mol wt 144.13.
C 50.00%, H 5.59%, O 44.40%.