Fumaric acid

Fumaric acid


IUPAC name	(E)-Butenedioic acid
Other names	trans-1,2-Ethylenedicarboxylic acid 2-Butenedioic acid Allomaleic acid Boletic acid Lichenic acid
Identifiers
CAS number	110-17-8
EINECS number	203-743-0
SMILES	OC(=O)C=CC(=O)O
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 (pK_a)	pk_a1 = 3.03, pk_a2 = 4.44
Hazards
EU classification	Irritant (Xi)
R-phrases	R36
S-phrases	S26
Related Compounds
Related carboxylic acids	Succinic acid
Related compounds	Fumaryl chloride Fumaronitrile Dimethyl fumarate Iron(II) fumarate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Fumaric acid is the esters of fumaric acid are known as fumarates.

Fumaric acid, when added to food products, is denoted by E number E297.

Biology

Fumaric acid is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss.

Fumarate is an intermediate in the sunlight.^{[citation needed]}

Fumarate is also a byproduct of the urea cycle.

Medicine

Fumaric acid Side-effects include kidney or gastrointestinal disorders, as well as skin flushing; these are mainly caused by excess intake. Decreased white blood cell counts have been reported with prolonged use.^{[citation needed]}

Food

Fumaric acid is a food acidulent used since 1946 because it is non-toxic. It is generally used in beverages and baking powders for which requirements are placed on purity. It is generally used as a substitute for malic acid is used.

Chemistry

Fumaric acid is inexpensive, so it is typically purchased rather than prepared. It was first prepared from bromocatalyst.^[2]

The chemical properties of fumaric acid can be anticipated from its component dienophile.

Other uses

Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.

Safety

Fumaric acid converts to the irritant maleic anhydride, upon partial combustion.

References

^ Volhard, J. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. DOI: 10.1002/jlac.18922680108
^ Milas, N. A. "Fumaric Acid" Organic Synthesis 1943, Collective Volume 2, page 302. Online version