Fumaric Acid

Title: Fumaric Acid
CAS Registry Number: 110-17-8
CAS Name: (2E)-2-Butenedioic acid
Additional Names: trans-1,2-ethylenedicarboxylic acid; allomaleic acid; boletic acid
Molecular Formula: C4H4O4
Molecular Weight: 116.07
Percent Composition: C 41.39%, H 3.47%, O 55.14%
Literature 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, liq ammonia.
Melting point: mp 287° (closed capillary, rapid heating)
pKa: pK1 (25°): 3.03; pK2: 4.54
Density: d 1.625
Derivative Type: Monomethyl ester
Molecular Formula: C5H6O4
Molecular Weight: 130.10
Percent Composition: C 46.16%, H 4.65%, O 49.19%
Properties: Prisms from alc, mp 144.5°.
Melting point: mp 144.5°
Derivative Type: Dimethyl ester
Molecular Formula: C6H8O4
Molecular Weight: 144.13
Percent Composition: C 50.00%, H 5.59%, O 44.40%
Properties: Crystals, mp 102°. bp 192°.
Melting point: mp 102°
Boiling point: bp 192°
Use: Substitute for tartaric acid in beverages and baking powders; as a replacement or partial replacement for citric acid in fruit drinks. As an antioxidant. Manuf polyhydric alcohols, synthetic resins. As mordant in dyeing.
Fumigatin Fungichromin Fungisterol Funtumine Fura-2

Fumaric acid
Skeletal formula of fumaric acid
Ball-and-stick model of the fumaric acid molecule
Identifiers
CAS number 110-17-8 YesY
ChemSpider 10197150 YesY
UNII 88XHZ13131 YesY
EC number 203-743-0
DrugBank DB04299
KEGG C00122 YesY
ChEBI CHEBI:18012 YesY
ChEMBL CHEMBL503160 YesY
ATC code D05AX01
Jmol-3D images Image 1
Properties
Molecular formula C4H4O4
Molar mass 116.07 g/mol
Appearance White solid
Density 1.635 g/cm³, solid
Melting point 287 °C
Solubility in water 0.63 g/100 mL
Acidity (pKa) pka1 = 3.03, pka2 = 4.44
Hazards
EU classification Irritant (Xi)
R-phrases R36
S-phrases (S2) S26
NFPA 704
NFPA 704.svg
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Related compounds
Related carboxylic acids maleic acid
succinic acid
crotonic acid
Related compounds fumaryl chloride
fumaronitrile
dimethyl fumarate
iron(II) fumarate
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Fumaric acid or trans-butenedioic acid is the chemical compound with the formula HO2CCH=CHCO2H. This white crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid. In fumaric acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z). Fumaric acid has a fruit-like taste. The salts and esters are known as fumarates. Dimethyl fumarate significantly reduces disability progression in multiple sclerosis.