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 &nbsp;°C and a [[boiling point]] of 235 &nbsp;°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]] [[fi:Meripihkahappo]] [[sv:Bärnstenssyra]] [[zh:琥珀酸]]