Succinic acid

Succinic acid

Chembox new
Name = Succinic acid
ImageFile = Kwas_bursztynowy007.svg
ImageFile1 = Succinic-acid-3D-balls.png IUPACName = Butanedioic acid
OtherNames = ethane-1,2-dicarboxylic acid
Section1 = Chembox Identifiers
CASNo = 110-15-6
ChemSpiderID = 1078
SMILES = OC(CCC(O)=O)=O
Section2 = Chembox Properties
Formula = C4H6O4
MolarMass = 118.09 g/mol
Density = 1.56 g/cm³
MeltingPt = 185–187 °C
BoilingPtC = 235

Succinic acid (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.

Physical properties

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. The carboxylate anion is called "succinate" and esters of succinic acid are called "alkyl succinates".

Biochemical role

Succinate is a component of the citric acid cycle and is capable of donating electrons to the electron transfer chain via the following reaction:

:succinate + FAD → fumarate + FADH2

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.

History

Spirit of amber was 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.

afety

The acid is combustible and corrosive, capable of causing burns. "Harmful by inhalation, ingestion and through skin absorption. Wash after handling. Eye contact may cause serious damage."

In nutraceutical form as a food additive and dietary supplement, is safe and approved by the FDA.

Reactions

Succinic acid can be converted to fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation.

Fermentation

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. [Peynaud, Emile (1984) Knowing and Making Wine.]

References

*1728

ee also

*Oil of amber, procured by heating succinic acid

External links

* [http://physchem.ox.ac.uk/MSDS/SU/succinic_acid.html MSDS Data]
* [http://www.cfsan.fda.gov/~dms/eafus.html FDA]
* [http://chemicalland21.com/industrialchem/organic/SUCCINIC%20ACID.htm Succinic Acid]


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Look at other dictionaries:

  • succinic acid — [sək sin′ik] n. [Fr succinique < L succinum, amber] a colorless, crystalline dibasic acid, HOOC(CH2) 2COOH, found in amber, lignite, and many plants, and produced synthetically or during alcoholic fermentation: it is used in medicine and… …   English World dictionary

  • succinic acid — Chem. a colorless, crystalline, water soluble solid, C4H6O4, used chiefly in the manufacture of lacquers, dyes, and perfume. [1780 90] * * * ▪ chemical compound also called  Butanedioic Acid,         a dicarboxylic acid of molecular formula… …   Universalium

  • succinic acid — gintaro rūgštis statusas T sritis chemija formulė (HOOCCH₂)₂ atitikmenys: angl. amber acid; succinic acid rus. янтарная кислота ryšiai: sinonimas – butano dirūgštis …   Chemijos terminų aiškinamasis žodynas

  • succinic acid — An intermediate in the tricarboxylic acid cycle; several of its salts have been variously used in medicine. * * * suc·cin·ic acid (.)sək .sin ik n a crystalline dicarboxylic acid C4H6O4 that is found widely in nature, that is formed in the Krebs… …   Medical dictionary

  • succinic acid — /sʌkˌsɪnɪk ˈæsəd/ (say suk.sinik asuhd) noun a white crystalline soluble acid, (CH2)2(COOH)2, which is found in nearly all cells as an intermediate in the citric acid cycle. It occurs naturally in amber and is manufactured synthetically and used… …  

  • succinic acid — noun Etymology: French succinique, from Latin succinum amber Date: 1790 a crystalline dicarboxylic acid C4H6O4 found widely in nature and active in energy yielding metabolic reactions …   New Collegiate Dictionary

  • succinic acid — noun A colourless crystalline dicarboxylic acid, (CHCOOH), that occurs naturally in amber and is important in the metabolic Krebs cycle. Syn: E363 …   Wiktionary

  • succinic acid — [sʌk sɪnɪk] noun Biochemistry a crystalline organic acid which occurs in living tissue as an intermediate in glucose metabolism. Origin C18: from Fr. succinique, from L. succinum amber (from which it was first derived) …   English new terms dictionary

  • succinic acid — n. Chem. a crystalline dibasic acid derived from amber etc. Derivatives: succinate n. Etymology: F succinique f. L succinum amber …   Useful english dictionary

  • succinic acid — suc•cin′ic ac′id [[t]səkˈsɪn ɪk[/t]] n. chem. a colorless, crystalline, water soluble solid, C4H6O4, used esp. in the manufacture of lacquers, dyes, and perfume • Etymology: 1780–90; < F succinique < L succinum amber …   From formal English to slang

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