succinic acid succinic acid succinic acid (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (ch2)2(co2h)2. in living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making atp, and as a signaling molecule reflecting the cellular metabolic state. succinic acid names preferred iupac name butanedioic acid other names succinic acid1,4-butanedioic acid identifiers cas number 110-15-6 y 3d model (jsmol) 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 cid 1110 unii ab6mnq6j6l y comptox dashboard (epa) dtxsid6023602 inchi inchi=1s/c4h6o4/c5-3(6)1-2-4(7)8/h1-2h2,(h,5,6)(h,7,8) ykey: kdyfgrwqoybrfd-uhfffaoysa-n yinchi=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 118.088 g·mol−1 density 1.56 g/cm3 melting point 184–190 °c (363–374 °f; 457–463 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 = 4.2pka2 = 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 acidmalonic acidbutyric acidmalic acidtartaric acidfumaric acidvaleric acidglutaric acid except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references succinate is generated in mitochondria via the tricarboxylic acid cycle (tca). succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. as such, succinate links cellular metabolism, especially atp formation, to the regulation of cellular function. dysregulation of succinate synthesis, and therefore atp synthesis, happens in some genetic mitochondrial diseases, such as leigh syndrome, and melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury. succinic acid is marketed as food additive e363. the name derives from latin succinum, meaning amber. physical properties succinic acid is a white, odorless solid with a highly acidic taste. in an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/ˈsʌksɪneɪt/). as a diprotic acid, succinic acid undergoes two successive deprotonation reactions: (ch2)2(co2h)2 → (ch2)2(co2h)(co2)− + h+ (ch2)2(co2h)(co2)− → (ch2)2(co2)22− + h+ the pka of these processes are 4.3 and 5.6, respectively. both anions are colorless and can be isolated as the salts, e.g., na(ch2)2(co2h)(co2) and na2(ch2)2(co2)2. in living organisms, primarily succinate, not succinic acid, is found. as a radical group it is called a succinyl (/ˈsʌksɪnəl/) group. like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. commercial production historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. succinate is also produced from butane via maleic anhydride. global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. genetically engineered escherichia coli and saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose. chemical reactions succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (ch2co2ch2ch3)2. this diethyl ester is a substrate in the stobbe condensation. dehydration of succinic acid gives succinic anhydride. succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. applications in 2004, succinate was placed on the us department of energy's list of top 12 platform chemicals from biomass. precursor to polymers, resins, and solvents succinic acid is a precursor to some polyesters and a component of some alkyd resins. 1,4-butanediol (bdo) can be synthesized using succinic acid as a precursor. the automotive and electronics industries heavily rely on bdo to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. acylation with succinic acid is called succination. oversuccination occurs when more than one succinate adds to a substrate. food and dietary supplement as a food additive and dietary supplement, succinic acid is generally recognized as safe by the u.s. food and drug administration. succinic acid is used primarily as an acidity regulator in the food and beverage industry. it is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. as an excipient in pharmaceutical products, it is also used to control acidity or as a counter ion. drugs involving succinate include metoprolol succinate, sumatriptan succinate, doxylamine succinate or solifenacin succinate. biosynthesis tricarboxylic acid (tca) cycle