Fumaric acid

Fumaric acid

IUPAC name[hide]
(E)-Butenedioic acid
Other names[hide]
trans-1,2-Ethylenedicarboxylic acid
2-Butenedioic acid
trans-butenedioic acid
Allomaleic acid
Boletic acid
Donitic acid
Lichenic acid
Identifiers

Molecular formula
Molar mass
Appearance
Density

Properties
C4H4O4
116.07 g/mol
White solid
1.635 g/cm, solid

Melting point

287 C

Solubility in water
Acidity (pKa)

0.63 g/100 mL
pka1 = 3.03, pka2 = 4.44

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.

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 citric acid cycle used by cells to produce energy in the
form of adenosine triphosphate (ATP) from food. It is formed by the oxidation of succinate
by the enzyme succinate dehydrogenase. Fumarate is then converted by the enzyme fumarase
to malate. Human skin naturally produces fumaric acid when exposed to sunlight.[citation needed]
Fumarate is also a product of the urea cycle.

Medicine
A fumaric acid ester is currently under investigation for treatment of multiple sclerosis.[1]

Food
As a food additive, it is used as an acidity regulator and is denoted by the E number E297.
Fumaric acid is a food acidulent used since 1946. 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 tartaric acid and occasionally in place of citric acid, at a rate of 1.36 g
of citric acid to every 0.91 grams of fumaric acid to add sourness, similar to the way malic
acid is used. It is also used as a coagulant in stovetop pudding mixes.
It is approved for use as a food additive in the EU[2], USA[3] and Australia and New Zealand[4]
(where it is listed by its INS number 297).

Chemistry
Fumaric acid was first prepared from succinic acid.[5] A traditional synthesis involves
oxidation of furfural (from the processing of maize) using chlorate in the presence of a
vanadium-based catalyst.[6] Currently, industrial synthesis of fumaric acid is mostly based on
catalytic isomerisation of maleic acid in aqueous solutions at low pH. Maleic acid is
accessible in large volumes as a hydrolysis product of maleic anhydride, produced by
catalytic oxidation of benzene or butane.[7]
The chemical properties of fumaric acid can be anticipated from its component functional
groups. This weak acid forms a diester, it undergoes additions across the double bond, and it
is an excellent dienophile.
Fumaric acid does not combust in a bomb calorimeter under conditions where maleic acid
deflagrates smoothly. For teaching experiments designed to measure the difference in energy
between the cis- and trans- isomers, a measured quantity of carbon can be ground with the
subject compound and the enthalpy of combustion computed by difference.

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.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [8]
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Citric_acid_cycle edit

See also

Dermatology

Photosynthesis

Maleic acid, the cis-isomer of fumaric acid

References
1. ^ Moharregh-Khiabani, D.; Linker, R.; Gold, R.; Stangel, M. (2009). "Fumaric Acid
and its esters: an emerging treatment for multiple sclerosis". Current
neuropharmacology 7 (1): 6064. DOI:10.2174/157015909787602788.
PMC 2724664. PMID 19721818. edit
2. ^ UK Food Standards Agency: "Current EU approved additives and their E
Numbers". Retrieved 2011-10-27.
3. ^ US Food and Drug Administration: "Listing of Food Additives Status Part II".
Retrieved 2011-10-27.
4. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of
ingredients". Retrieved 2011-10-27.
5. ^ Volhard, J. "Darstellung von Malensureanhydrid" Justus Liebig's Annalen der
Chemie 1892, volume 268, page 255-6. doi:10.1002/jlac.18922680108
6. ^ Milas, N. A. "Fumaric Acid" Organic Synthesis 1943, Collective Volume 2, page
302. Online version
7. ^ British Patent No. 775,912, publicated on the May 29, 1957, by Monsanto Chemical
Company.
8. ^ The interactive pathway map can be edited at WikiPathways: "TCA_Cycle_WP78".
http://en.wikipedia.org/wiki/Fumaric_acid