Succinic acid

Succinic acid
IUPAC name Butanedioic acid
Other names ethane-1,2-dicarboxylic acid
Identifiers
CAS number	110-15-6 Y
PubChem	1110
ChemSpider	1078 Y
UNII	AB6MNQ6J6L Y
DrugBank	DB00139
ChEBI	CHEBI:15741 Y
ChEMBL	CHEMBL576 Y
Jmol-3D images	Image 1
SMILES C(CC(=O)O)C(=O)O
InChI InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Y Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N Y InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Key: KDYFGRWQOYBRFD-UHFFFAOYAC
Properties
Molecular formula	C4H6O4
Molar mass	118.09 g mol−1
Density	1.56 g/cm3
Melting point	184 °C (363 °F; 457 K)
Boiling point	235 °C (455 °F; 508 K)
Solubility in water	58 g/L (20 °C)
Acidity (pKa)	pKa1 = 4.2 pKa2 = 5.6
Hazards
Flash point	206 °C (403 °F; 479 K)
Related compounds
Other anions	sodium succinate
Related carboxylic acids	propionic acid malonic acid butyric acid malic acid tartaric acid fumaric acid valeric acid glutaric acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Succinic acid (/səkˈsɪnɨk/; 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

Spirit of amber was originally obtained from amber by pulverising and distilling it using a sand bath.

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 can be converted into fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation. Dehydration of succinic acid gives succinic anhydride.

Applications

Succinic acid is a precursor to some specialized polyesters. It is also a component of some alkyd resins.

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.

Biochemistry

Succinate is an intermediate in the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:

succinate + FAD → fumarate + FADH₂.

Click on genes, proteins and metabolites below to link to respective articles.

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|{{{bSize}}}px|alt=TCA Cycle edit|]]

File:TCACycle WP78.png

TCA Cycle edit

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.

Fermentation

See also: Acids in wine

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.

Succinates

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.

Safety

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.

See also

• Oil of amber, procured by heating succinic acid.

References

•  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. 

External links

• MSDS Data
• FDA
• Succinic Acid
• Calculator: Water and solute activities in aqueous succinic acid