Succinic acid
| Succinic acid | |
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Butanedioic acid |
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Other names
ethane-1,2-dicarboxylic acid |
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| Identifiers | |
| CAS number | 110-15-6  |
| PubChem | 1110 |
| ChemSpider | 1078 |
| UNII | AB6MNQ6J6L |
| DrugBank | DB00139 |
| ChEBI | CHEBI:15741 |
| ChEMBL | CHEMBL576 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O4 |
| Molar mass | 118.09 g mol−1 |
| Density | 1.56 g/cm3[1] |
| Melting point |
184 °C, 457 K, 363 °F ([1]) |
| Boiling point |
235 °C, 508 K, 455 °F ([1]) |
| Solubility in water | 58 g/L (20 °C)[1] |
| Acidity (pKa) | pKa1 = 4.2 pKa2 = 5.6 |
| Hazards | |
| Flash point | 206 °C (403 °F)[1] |
| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Succinic acid (pron.: /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.
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Production and reactions [edit]
Spirit of amber was originally obtained from amber by pulverising and distilling it using a sand bath. In the past it was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.
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.[2]
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.[3]
Applications [edit]
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.[4] Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[5]
In nutraceutical form as a food additive and dietary supplement, is safe and approved by the U.S. Food and Drug Administration.[6] As an excipient in pharmaceutical products it is used to control acidity[7] and, more rarely, in effervescent tablets.[8]
Biochemistry [edit]
Succinate is an intermediate in the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:
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.
Fermentation [edit]
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.[9]
Succinates [edit]
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 [edit]
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.[10]
See also [edit]
- Oil of amber, procured by heating succinic acid.
References [edit]
- ^ a b c d e Record in the GESTIS Substance Database from the IFA
- ^ Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523
- ^ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932), "Succinic Anhydride", Org. Synth. 12: 66; Coll. Vol. 2: 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
- ^ http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm
- ^ http://drugtopics.modernmedicine.com/drugtopics/Drugtopics.com+Exclusives/Overview-of-pharmaceutical-excipients-used-in-tabl/ArticleStandard/Article/detail/561047
- ^ Lachman, Leon; Joseph B. Schwartz (1990). Pharmaceutical Dosage Forms--tablets. p. 288. ISBN 0-8247-8044-2, 9780824780449 Check
|isbn=value (help). - ^ Peynaud, Emile (1984) Knowing and Making Wine.
- ^ MSDS
This article incorporates text from a publication now in the public domain: Chambers, Ephraim, ed. (1728). "article name needed". Cyclopaedia, or an Universal Dictionary of Arts and Sciences (first ed.). James and John Knapton, et al.
External links [edit]
| Citric Acid Cycle Metabolic Pathway | ||||||||||||||||||
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| Oxaloacetate | Malate | Fumarate | Succinate | Succinyl-CoA | ||||||||||||||
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| Acetyl-CoA | NADH + H+ | NAD+ | H2O | FADH2 | FAD | CoA + ATP(GTP) | Pi + ADP(GDP) | |||||||||||
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+ | H2O |  |
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NADH + H+ + CO2 | |||||||||||||
| CoA | NAD+ | |||||||||||||||||
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H2O |  |
H2O |  |
NAD(P)+ | NAD(P)H + H+ |  |
CO2 |  |
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| Citrate | cis-Aconitate | Isocitrate | Oxalosuccinate | α-Ketoglutarate | ||||||||||||||
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