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Succinate

Succinic acid
Bernsteinsäure2.svg
Succinic-acid-3D-balls.png
Sample of succinic acid.jpg
Names
Preferred IUPAC name
Butanedioic acid
Other names
Succinic acid
Ethane-1,2-dicarboxylic acid
Identifiers
110-15-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:15741 YesY
ChEMBL ChEMBL576 YesY
ChemSpider 1078 YesY
DrugBank DB00139 YesY
ECHA InfoCard 100.003.402
E number E363 (antioxidants, ...)
3637
PubChem 1110
UNII AB6MNQ6J6L YesY
Properties
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)
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
-57.9·10−6 cm3/mol
Hazards
Flash point 206 °C (403 °F; 479 K)
Related compounds
Other anions
sodium succinate
propionic acid
malonic acid
butyric acid
malic acid
tartaric acid
fumaric acid
valeric acid
glutaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Succinic acid (/səkˈsɪnk/) is a dicarboxylic acid with chemical formula (CH2)2(CO2H)2. It is a white, odorless solid. In an aqueous solution, it ionizes to anions (that is, conjugates to a conjugate base) called succinate (/ˈsʌksnt/), which plays a role in the citric acid cycle, an energy-yielding process in all living organisms. As a radical group it is called a succinyl (/ˈsʌksnəl/) group. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

Common industrial routes include partial hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol.


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