Succinic acid
97039
224372229
2008-07-08T15:49:06Z
131.227.175.169
{{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
| SMILES = OC(CCC(O)=O)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>4</sub>
| 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 [[ester]]s of succinic acid are called ''alkyl succinates''.
==Biochemical role==
Succinate is a component of the [[citric acid cycle]] and is capable of donating [[electron]]s to the [[electron transfer chain]] via the following reaction:
:succinate + [[FAD]] → [[fumarate]] + [[FADH2|FADH<sub>2</sub>]]
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 Fe<sub>2</sub>S<sub>2</sub> 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 [[gleet]]s.
==Safety==
The acid is [[combustion|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.<ref>Peynaud, Emile (1984) Knowing and Making Wine.</ref>
==References==
<references/>
*{{1728}}
==See 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]
{{citric acid cycle}}
[[Category:Citric acid cycle compounds]]
[[Category:Dicarboxylic acids]]
[[bg:Янтарна киселина]]
[[da:Ravsyre]]
[[de:Bernsteinsäure]]
[[el:Ηλεκτρικό οξύ]]
[[es:Ácido succínico]]
[[fr:Acide succinique]]
[[it:Acido succinico]]
[[lv:Dzintarskābe]]
[[hu:Szukcinilsav]]
[[nl:Barnsteenzuur]]
[[ja:コハク酸]]
[[pl:Kwas bursztynowy]]
[[pt:Ácido succínico]]
[[ru:Янтарная кислота]]
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