|Jmol interactive 3D||Image|
|Molar mass||118.09 g·mol−1|
|Melting point||184 °C (363 °F; 457 K)|
|Boiling point||235 °C (455 °F; 508 K)|
|58 g/L (20 °C) or 100 mg/mL|
|Solubility in Methanol||158 mg/mL|
|Solubility in Ethanol||54 mg/mL|
|Solubility in Acetone||27 mg/mL|
|Solubility in Glycerol||50 mg/mL|
|Solubility in Ether||8.8 mg/mL|
|Acidity (pKa)||pKa1 = 4.2
pKa2 = 5.6
|Flash point||206 °C (403 °F; 479 K)|
Related carboxylic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Succinic acid (//; IUPAC systematic name: butanedioic acid; historically known as spirit of amber) is a diprotic, dicarboxylic acid with chemical formula C4H6O4 and structural formula HOOC-(CH2)2-COOH. It is a white, odorless solid. Succinate plays a role in the citric acid cycle, an energy-yielding process. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.
Production and reactions
Succinic acid is produced by several methods. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. More recently, succinic acid has been produced through the fermentation of glucose from renewable feedstock and purification of raw bio-based succinic acid.
Succinic acid is used in the food and beverage industry, primarily as an acidity regulator. Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%. The growth can be attributed to advances in industrial biotechnology that seek to displace petroleum-based chemicals in industrial applications. Companies such as BioAmber, Reverdia, Myriant, BASF and Purac are progressing from demonstration scale production of bio-based succinic acid to viable commercialization.
It is also sold as a food additive and dietary supplement, and is generally recognized as safe for those uses by the U.S. Food and Drug Administration. As an excipient in pharmaceutical products it is used to control acidity and, more rarely, in effervescent tablets.
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
- The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".
This conversion is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC). The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three 2Fe-2S clusters part of subunit B.
Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity.
Salts formed by neutralizing succinic acid are called succinates. One example is sodium succinate, a white, water-soluble salt. Esters of succinic acid are also called succinates, one example being dimethylsuccinate with the formula (CH2CO2CH3)2.
Succinic acid is an important biochemical intermediate that occurs in all living creatures. Like other simple mono- and dicarboxylic acids, it is not considered dangerous, although it is a skin irritant.
- Oil of amber, procured by heating succinic acid.
- Record in the GESTIS Substance Database of the IFA
- "Product Information Sheet: Succinic Acid" (PDF). Sigma Aldrich. Retrieved 7 November 2015.
- Chambers, E., ed. (1728). "Spirit of Amber". Cyclopaedia. p. 75.
- Boy Cornils, Peter Lappe (2005), "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523
- "Life Cycle Analysis (LCA)". BioAmber Inc.
- Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Org. Synth. 12: 66.; Coll. Vol. 2, p. 560.
- Zeikus, J. G.; Jain, M. K.; Elankovan, P. (1999). "Biotechnology of succinic acid production and markets for derived industrial products". Applied Microbiology and Biotechnology 51 (5): 545. doi:10.1007/s002530051431.
- NNFCC Renewable Chemicals Factsheet: Succinic Acid
- FDA GRAS Database. Succinic acid in the FDA SCOGS Database
- "Overview of pharmaceutical excipients used in tablets and capsules". Modern Medicine Network. 24 October 2008. Retrieved 7 November 2015.
- Lachman, Leon; Joseph B. Schwartz (1990). Pharmaceutical Dosage Forms--tablets. p. 288. ISBN 9780824780449.
- Peynaud, Emile (1984). Knowing and Making Wine.
- "Succinic Acid MSDS" (PDF). BioAmber Inc.
- This article incorporates text from a publication now in the public domain: Chambers, Ephraim, ed. (1728). "Amber". Cyclopædia, or an Universal Dictionary of Arts and Sciences 1 (first ed.). James and John Knapton, et al. p. 75.
|Citric acid cycle metabolic pathway|
|Acetyl-CoA||NADH + H+||NAD+||H2O||FADH2||FAD||CoA + ATP(GTP)||Pi + ADP(GDP)|
|+||H2O||NADH + H+ + CO2|
|H2O||H2O||NAD(P)+||NAD(P)H + H+||CO2|