| 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 pentanoic 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 ( /səkˈsɪnɨk/; IUPAC systematic name: butanedioic acid; historically known as spirit of amber) is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.
The carboxylate anion is called succinate and esters of succinic acid are called alkyl succinates.
At room temperature, pure succinic acid is a solid that forms colorless, odorless crystals. It has a melting point of 185 °C and a boiling point of 235 °C. It is a diprotic acid.
Contents |
Spirit of amber was originally procured from amber by pulverising and distilling it using a sand bath. It was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.
Succinic acid is now used within the food and beverage industry, primarily as a sweetener. Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[2]
Succinate is a component of the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:
This 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 Fe2S2 clusters part of subunit B.
Succinic acid can be converted to fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation.
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.[3]
Click on genes, proteins and metabolites below to link to respective articles.[4]
The acid is combustible and corrosive, capable of causing burns.
In nutraceutical form as a food additive and dietary supplement, is safe and approved by the U.S. Food and Drug Administration.[5] As an excipient in pharmaceutical products it is used to control acidity[6] and, more rarely, in effervescent tablets.[7]
| Oxaloacetate | Malate | Fumarate | Succinate | Succinyl-CoA | ||||||||||||||
| Acetyl-CoA | NADH + H+ | NAD+ | H2O | FADH2 | FAD | CoA + ATP(GTP) | Pi + ADP(GDP) | |||||||||||
| + | H2O | NADH + H+ + CO2 | ||||||||||||||||
| CoA | NAD+ | |||||||||||||||||
| H2O | H2O | NAD(P)+ | NAD(P)H + H+ | CO2 | ||||||||||||||
| Citrate | cis-Aconitate | Isocitrate | Oxalosuccinate | α-Ketoglutarate | ||||||||||||||
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