Fumaric acid

Chembox new
Name = Fumaric acid
ImageFile = Fumaric-acid-2D-skeletal.png ImageSize = 200px
ImageName = Skeletal formula of fumaric acid
ImageFile1 = Fumaric-acid-3D-balls.png ImageSize1 = 200px
ImageName1 = Ball-and-stick model of the fumaric acid molecule
IUPACName = (E)-Butenedioic acid
OtherNames = "trans"-1,2-Ethylenedicarboxylic acid
2-Butenedioic acid
Allomaleic acid
Boletic acid
Lichenic acid
Section1 = Chembox Identifiers
SMILES = OC(=O)C=CC(=O)O
CASNo = 110-17-8
EINECS = 203-743-0
CoE = 25
FEMA = 2488
JECFA = 618
FDA = 172.350
Section2 = Chembox Properties
Formula = C₄H₄O_{4
MolarMass = 116.07 g/mol
Appearance = White solid
Density = 1.635 g/cm³, solid
Solubility = 0.63 g/100 mL
MeltingPt = 287 °C
pKa = p"k"a1 = 3.03, p"k"a2 = 4.44}
Section7 = Chembox Hazards
EUClass = Irritant (Xi)
RPhrases = R36
SPhrases = S2 S26
Section8 = Chembox Related
Function = carboxylic acids
OtherFunctn = Maleic acid
Succinic acid
OtherCpds = Fumaryl chloride
Fumaronitrile
Dimethyl fumarate
Iron(II) fumarate

Fumaric acid is the chemical compound with the formula HO₂CCH=CHCO₂H. This colorless crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis. It has a fruit-like taste. The salts and 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 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.Fact|date=November 2007

Fumarate is also a byproduct of the urea cycle.

Medicine

Fumaric acid esters are sometimes used to treat psoriasis, as it has been suggested that the condition is caused by an impairment of fumaric acid production in the skin.Fact|date=November 2007 A starting dose is 60-105 mg daily, which may be gradually increased to as much as 1,290 mg per day. Side-effects include kidney or gastrointestinal disorders, as well as skin flushing; these are mainly caused by excess intake. Decreased white blood cell (WBC) counts have been reported with prolonged use.Fact|date=November 2007

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 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 for the same taste. It is also used in candy to add sourness, similar to the way malic acid is used.

Chemistry

Fumaric acid was first prepared from succinic acid. [Volhard, J. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. DOI: 10.1002/jlac.18922680108] A traditional synthesis involves oxidation of furfural (from the processing of maize) using sodium chlorate in the presence of a vanadium-based catalyst. [Milas, N. A. "Fumaric Acid" "Organic Synthesis" 1943, Collective Volume 2, page 302. [http://www.orgsyn.org/orgsyn/pdfs/CV2P0302.pdf Online version] ] Nowadays industrial synthesis of fumaric acid is mostly based on catalytic isomerisation of maleic acid (which in turn is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane) in aqueous solutions. [British Patent No. 775,912, publicated on the May 29, 1957, by Monsanto Chemical Company.]

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.

Other uses

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

afety

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

ee also

*Dermatology
*Photosynthesis
*Maleic acid, the cis-isomer of fumaric acid

References

External links

* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc11/icsc1173.htm International Chemical Safety Card 1173]