Succinic acid

Succinic acid

Names
Preferred IUPAC name Butanedioic acid
Other names Succinic acid Ethane-1,2-dicarboxylic acid
Identifiers
CAS Number	110-15-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15741 Y
ChEMBL	ChEMBL576 Y
ChemSpider	1078 Y
DrugBank	DB00139 Y
ECHA InfoCard	100.003.402
E number	E363 (antioxidants, ...)
IUPHAR/BPS	3637
PubChem	1110
UNII	AB6MNQ6J6L Y
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
SMILES C(CC(=O)O)C(=O)O
Properties
Chemical 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) 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
Magnetic susceptibility (χ)	-57.9·10−6 cm3/mol
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Succinic acid (/səkˈsɪnᵻk/) 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 (/ˈsʌksᵻneɪt/), 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 (/ˈsʌksᵻnəl/) 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.