Fumaric acid
Template:Short description Template:DMCA Page Template:Chembox/styles.css has no content.
Template:Chembox IndexlistTemplate:Chembox CompToxTemplate:Chembox GHS (set)Template:Chembox Datapage check| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Names | |
|---|---|
| Preferred IUPAC name
(2E)-But-2-enedioic acid | |
| Other names
Page Template:Plainlist/styles.css has no content.
| |
| Identifiers | |
| Page Template:Plainlist/styles.css has no content. | |
3D model (JSmol)
|
Page Template:Plainlist/styles.css has no content. |
| 605763 | |
| ChEBI | Page Template:Plainlist/styles.css has no content. |
| ChEMBL | Page Template:Plainlist/styles.css has no content. |
| ChemSpider | Page Template:Plainlist/styles.css has no content. |
| DrugBank | Page Template:Plainlist/styles.css has no content. |
| EC Number | Page Template:Plainlist/styles.css has no content. |
| 49855 | |
| KEGG | Page Template:Plainlist/styles.css has no content. |
PubChem CID
|
Page Template:Plainlist/styles.css has no content. |
| RTECS number | Page Template:Plainlist/styles.css has no content. |
| UNII | Page Template:Plainlist/styles.css has no content. |
| UN number | 9126 |
| |
| Properties | |
| C4H4O4 | |
| Molar mass | 116.072 g·mol−1 |
| Appearance | White solid |
| Density | 1.635 g/cm3 |
| Melting point | 287 °C (549 °F; 560 K) (decomposes)[2] |
| 6.3 g/L at 25 °C[1] | |
| Acidity (pKa) | pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer) |
| −49.11·10−6 cm3/mol | |
| non zero | |
| Pharmacology | |
| D05AX01 (WHO) | |
| Hazards | |
| NFPA 704 (fire diamond) | Page Template:NFPA 704 diamond/styles.css has no content. |
| 375 °C (707 °F; 648 K) | |
| Related compounds | |
Related carboxylic acids
|
Page Template:Plainlist/styles.css has no content. |
Related compounds
|
Page Template:Plainlist/styles.css has no content. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Template:Chembox Footer/trackingTemplate:Short description
Fumaric acid or trans-butenedioic acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297.[3] The salts and esters are known as fumarates. Fumarate can also refer to the C
4H
2O2−
4 ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Biosynthesis and occurrence
It is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase.
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.[4][5]
Fumarate is also a product of the urea cycle.
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
- ^ The interactive pathway map can be edited at WikiPathways: Page Module:Citation/CS1/styles.css has no content."TCACycle_WP78".
Uses
Food
Fumaric acid has been used as a food acidulant since 1946. It is approved for use as a food additive in the EU,[6] USA[7] and Australia and New Zealand.[8] 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. Fumaric acid is used in the making of wheat tortillas as a food preservative and as the acid in leavening.[9] 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 stove-top pudding mixes.
The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found in 2014 that fumaric acid is "practically non-toxic" but high doses are probably nephrotoxic after long-term use.[11]
Medicine
Fumaric acid was developed as a medicine to treat the autoimmune condition psoriasis in the 1950s in Germany as a tablet containing 3 esters, primarily dimethyl fumarate, and marketed as Fumaderm by Biogen Idec in Europe. Biogen would later go on to develop the main ester, dimethyl fumarate, as a treatment for multiple sclerosis.
In patients with relapsing-remitting multiple sclerosis, the ester 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.[12]
Other uses
Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes.
Fumaric acid can be used to make 6-methylcoumarin.[13]
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.[14]
Synthesis
Fumaric acid is produced based on catalytic isomerisation of maleic acid in aqueous solutions at low pH. It precipitates from the reaction solution. Maleic acid is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane.[3]
Historic and laboratory routes
Fumaric acid was first prepared from succinic acid.[15] A traditional synthesis involves oxidation of furfural (from the processing of maize) using chlorate in the presence of a vanadium-based catalyst.[16]
Reactions
The chemical properties of fumaric acid can be anticipated from its component functional groups. This weak acid forms a diester, it undergoes bromination across the double bond,[17] and it is a good dienophile.
Safety
See also
- Citric acid cycle (TCA cycle)
- Fumarate reductase
- Photosynthesis
- Maleic acid, the cis isomer of fumaric acid
- Succinic acid
References
- ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Page Module:Citation/CS1/styles.css has no content.Pubchem. "Fumaric acid". pubchem.ncbi.nlm.nih.gov.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.Lohbeck, Kurt; Haferkorn, Herbert; Fuhrmann, Werner; Fedtke, Norbert (2000). "Maleic and Fumaric Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_053. ISBN 3-527-30673-0.
- ^ Active Ingredients Used in Cosmetics: Safety Survey, Council of Europe. Committee of Experts on Cosmetic Products
- ^ Page Module:Citation/CS1/styles.css has no content."Fumaric Acid Foods". Archived from the original on 4 October 2014. Retrieved 22 April 2018.
- ^ UK Food Standards Agency: Page Module:Citation/CS1/styles.css has no content."Current EU approved additives and their E Numbers". Retrieved 27 October 2011.
- ^ US Food and Drug Administration: Page Module:Citation/CS1/styles.css has no content."Listing of Food Additives Status Part II". Food and Drug Administration. Archived from the original on 8 January 2010. Retrieved 27 October 2011.
- ^ Australia New Zealand Food Standards CodePage Module:Citation/CS1/styles.css has no content."Standard 1.2.4 - Labelling of ingredients". 8 September 2011. Retrieved 27 October 2011.
- ^ Page Module:Citation/CS1/styles.css has no content."Fumaric Acid - The Chemical Company". The Chemical Company. Retrieved 22 April 2018.
- ^ Page Module:Citation/CS1/styles.css has no content.Eats, Serious. "The Science Behind Salt and Vinegar Chips". www.seriouseats.com.
- ^ Page Module:Citation/CS1/styles.css has no content.European Commission (22 January 2003). "European Commission Report of the Scientific Committee on Animal Nutrition on the Safety of Fumaric Acid" (PDF). Retrieved 7 March 2014.
- ^ Page Module:Citation/CS1/styles.css has no content.Gold R.; Kappos L.; Arnold D.L.; et al. (20 September 2012). "Placebo-Controlled Phase 3 Study of Oral BG-12 for Relapsing Multiple Sclerosis". N Engl J Med. 367 (12): 1098–1107. doi:10.1056/NEJMoa1114287. hdl:2078.1/124401. PMID 22992073. S2CID 6614191.
- ^ Page Module:Citation/CS1/styles.css has no content.Thompson, T. J.; Edee, R. Herbert (1925). "Preparation of 6-Methylcoumarin and ITS Derivatives". Journal of the American Chemical Society. 47 (10): 2556–2559. Bibcode:1925JAChS..47.2556T. doi:10.1021/ja01687a019. ISSN 0002-7863.
- ^ Page Module:Citation/CS1/styles.css has no content."Scientists look to cut cow flatulence". phys.org. 21 March 2008.
- ^ Volhard, J. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. Script error: No such module "CS1 identifiers".
- ^ Page Module:Citation/CS1/styles.css has no content.Nicholas A. Milas (1931). "Fumaric Acid". Organic Syntheses. 11: 46. doi:10.15227/orgsyn.011.0046.
- ^ Page Module:Citation/CS1/styles.css has no content.Herbert S. Rhinesmith (1938). "α,β-Dibromosuccinic Acid". Organic Syntheses. 18: 17. doi:10.15227/orgsyn.018.0017.
External links
Template:Navbox bottom Template:Navbox top
Template:Navbox bottom Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found. Lua error in package.lua at line 80: module 'Module:Navbox/configuration' not found.
Lua error in package.lua at line 80: module 'Module:Authority control/config' not found.
