Title: Mesaconic Acid
CAS Registry Number: 498-24-8
CAS Name: (
E)-2-Methyl-2-butenedioic acid
Synonyms: methylfumaric acid;
trans-1-propene-1,2-dicarboxylic acid
Molecular Formula: C5H6O4
Molecular Weight: 130.10
Percent Composition: C 46.16%, H 4.65%, O 49.19%
Literature References: Prepd by heating citraconic anhydride with nitric acid: Shriner
et al., Org. Synth. 11, 74 (1931); from ethyl itaconate: Jones
et al., J. Chem. Soc. 1954, 1865; from
N,N-diethyl-5-diethylamino-2,3-dihydro-3-furamide: Sauer
et al., J. Am. Chem. Soc. 81, 693 (1959). Obtained almost instantly by the action of sunlight on citraconic acid in ether + chloroform in the presence of a little bromine: Fittig, Langworthy,
Ber. 26, 46 (1893);
Ann. 304, 119, 149 (1899); by action of b-radiation on citraconic acid + bromine: Lavigne, Levine,
US 2979445 (1961 to California Res. Corp.).
Properties: Orthorhombic needles from alcohol, monoclinic tablets from ethyl acetate, mp 204-205°. d 1.466. Sublimes. bp 250° (decompn). K1 at 25° = 8.5 ′ 10-4; K2 = 15 ′ 10-6. 100 g water dissolves 2.7 g at 18° and 117.9 g at the boiling point; 100 g 90% alc dissolves 30.6 g at 17° and 95.7 g at the boiling point. Sol in ether; sparingly sol in chloroform, carbon disulfide and ligroin.
Melting point: mp 204-205°
Boiling point: bp 250° (decompn)
Density: d 1.466
Derivative Type: Dimethyl ester
Molecular Formula: C7H10O4
Molecular Weight: 158.15
Percent Composition: C 53.16%, H 6.37%, O 40.47%
Properties: Liq, bp 206°. d421 vac 1.12011.
nD20 1.45575. Sol in 122 parts water at 15°.
Boiling point: bp 206°
Index of refraction: nD20 1.45575
Density: d421 vac 1.12011
Derivative Type: Diethyl ester
Molecular Formula: C9H14O4
Molecular Weight: 186.21
Percent Composition: C 58.05%, H 7.58%, O 34.37%
Properties: Liq, bp 229°. d420 vac 1.04675.
n420 1.44936.
Boiling point: bp 229°
Index of refraction: n420 1.44936
Density: d420 vac 1.04675
