World Library  
Flag as Inappropriate
Email this Article

Fumaric acid

Article Id: WHEBN0000839112
Reproduction Date:

Title: Fumaric acid  
Author: World Heritage Encyclopedia
Language: English
Subject: Urea cycle, Malic acid, Succinic acid, Oxidative phosphorylation, Albert Szent-Györgyi
Collection: Citric Acid Cycle Compounds, Dicarboxylic Acids, Food Acidity Regulators, Food Additives, Fumarates, Urea Cycle
Publisher: World Heritage Encyclopedia

Fumaric acid

Fumaric acid
Skeletal formula of fumaric acid
Ball-and-stick model of the fumaric acid molecule
IUPAC name
(E)-Butenedioic acid
Other names
trans-1,2-Ethylenedicarboxylic acid
2-Butenedioic acid
trans-butenedioic acid
Allomaleic acid
Boletic acid
Donitic acid
Lichenic acid
ATC code D05
ChemSpider  Y
DrugBank  Y
EC number 203-743-0
Jmol-3D images Image
Molar mass 116.07 g·mol−1
Appearance White solid
Density 1.635 g/cm3
Melting point 287 °C (549 °F; 560 K) (decomp)[1]
4.3 g/L at 20°C[2]
Acidity (pKa) pka1 = 3.03, pka2 = 4.44
Irritant (Xi)
R-phrases R36
S-phrases (S2)-S26
NFPA 704
Related compounds
maleic acid
succinic acid
crotonic acid
Related compounds
fumaryl chloride
dimethyl fumarate
iron(II) fumarate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

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.


  • Chemistry 1
  • Biology 2
  • Uses 3
    • Food 3.1
    • Medicine 3.2
    • Other uses 3.3
  • Safety 4
  • Interactive pathway map 5
  • See also 6
  • References 7
  • External links 8


Fumaric acid was first prepared from succinic acid.[3] A traditional synthesis involves oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst.[4] 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.[5]

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.


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.[6]

Fumarate is also a product of the urea cycle.



Fumaric acid has been used a food acidulant since 1946. It is approved for use as a food additive in the EU,[7] USA[8] and Australia and New Zealand.[9] As a food additive, it is used as an acidity regulator and can be denoted by the E number E297. 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 g of fumaric acid to every ~1.5 g of citric acid, in order to add sourness, similarly to the way malic acid is used. As well as being a component of some artificial vinegar flavors, such as "Salt and Vinegar" flavored potato chips,[10] it is also used as a coagulant in stovetop pudding mixes.


In patients with relapsing-remitting multiple sclerosis, dimethyl fumarate (BG-12, Biogen) significantly reduced relapse and disability progression in a phase 3 trial. It activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.[11]

Other uses

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


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

It is "practically non-toxic" but high doses are probably nephrotoxic after long term use.[12]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

}px; border:solid #ccc 1px; background-color:white;">
|}px|alt=TCA Cycle edit]]
TCA Cycle edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78". 

See also


  1. ^ Fumaric acid, PubChem
  2. ^ Record in the GESTIS Substance Database of the IFA
  3. ^ Volhard, J. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. doi:10.1002/jlac.18922680108
  4. ^ Milas, N. A. "Fumaric Acid" Organic Synthesis 1943, Collective Volume 2, page 302. Online version
  5. ^ British Patent No. 775,912, publicated on the May 29, 1957, by Monsanto Chemical Company.
  6. ^ Active Ingredients Used in Cosmetics: Safety Survey, Council of Europe. Committee of Experts on Cosmetic Products
  7. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27. 
  8. ^ US Food and Drug Administration: "Listing of Food Additives Status Part II". Retrieved 2011-10-27. 
  9. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27. 
  10. ^
  11. ^ Gold R., Kappos L., Arnold D.L.; et al. (September 20, 2012). "Placebo-Controlled Phase 3 Study of Oral BG-12 for Relapsing Multiple Sclerosis". N Engl J Med 367 (12): 1098–1107.  
  12. ^ European Commission: "European Commission Report of the Scientific Committee on Animal Nutrition on the Safety of Fumaric Acid" (PDF). Retrieved 2014-03-07. 

External links

  • International Chemical Safety Card 1173
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.