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Succinic acid

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Succinic acid
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IUPAC name
Butanedioic acid
Other names
ethane-1,2-dicarboxylic acid
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110-15-6 7pxY
ChEBI CHEBI:15741 7pxY
ChEMBL ChEMBL576 7pxY
ChemSpider 1078 7pxY
DrugBank DB00139 7pxY
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C4H6O4
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Density 1.56 g/cm3[1]
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58 g/L (20 °C)[1]
Acidity (pKa) pKa1 = 4.2
pKa2 = 5.6
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Other anions
sodium succinate
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).
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Infobox references

Succinic acid (/səkˈsɪnɨk/; IUPAC systematic name: butanedioic acid; historically known as spirit of amber[2]) is a diprotic, dicarboxylic acid with chemical formula C4H6O4 and structural formula HOOC-(CH2)2-COOH. It is a white, odorless solid. Succinate plays a role in the citric acid cycle, an energy-yielding process. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

Production and reactions

Spirit of amber was originally obtained from amber by pulverising and distilling it using a sand bath.[2]

Succinic acid is produced by several methods. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol.[3] More recently, succinic acid has been produced through the fermentation of glucose from renewable feedstock and purification of raw bio-based succinic acid.[4]

Succinic acid can be converted into fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation. Dehydration of succinic acid gives succinic anhydride.[5]

Applications

Succinic acid is a precursor to some specialized polyesters. It is also a component of some alkyd resins.

Succinic acid is used in the food and beverage industry, primarily as an acidity regulator.[6] Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[7] The growth can be attributed to advances in industrial biotechnology that seek to displace petroleum-based chemicals in industrial applications. Companies such as BioAmber, Reverdia, Myriant, BASF and Purac are progressing from demonstration scale production of bio-based succinic acid to viable commercialization.

It is also sold as a food additive and dietary supplement, and is generally recognized as safe for those uses by the U.S. Food and Drug Administration.[8] As an excipient in pharmaceutical products it is used to control acidity[9] and, more rarely, in effervescent tablets.[10]

Biochemistry

Succinate is an intermediate in the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:

succinate + FADfumarate + FADH2.

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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|{{{bSize}}}px|alt=TCA Cycle edit||]]
  1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78". 

This conversion 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 2Fe-2S clusters part of subunit B.

Fermentation

See also: Acids in wine

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.[11]

Succinates

Salts formed by neutralizing succinic acid are called succinates. One example is sodium succinate, a white, water-soluble salt. Esters of succinic acid are also called succinates, one example being dimethylsuccinate with the formula (CH2CO2CH3)2.

Safety

Succinic acid is an important biochemical intermediate that occurs in all living creatures. Like other simple mono- and dicarboxylic acids, it is not considered dangerous, although it is a skin irritant.[12]

See also

References

  1. ^ a b c d e Record in the GESTIS Substance Database of the IFA
  2. ^ a b Chambers, E., ed. (1728). "Spirit of Amber". Cyclopaedia. p. 75. 
  3. ^ Boy Cornils, Peter Lappe (2005), "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523 
  4. ^ "Life Cycle Analysis (LCA)". BioAmber Inc. 
  5. ^ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Org. Synth. 12: 66. ; Coll. Vol. 2, p. 560 .
  6. ^ Zeikus, J. G.; Jain, M. K.; Elankovan, P. (1999). "Biotechnology of succinic acid production and markets for derived industrial products". Applied Microbiology and Biotechnology 51 (5): 545. doi:10.1007/s002530051431. 
  7. ^ NNFCC Renewable Chemicals Factsheet: Succinic Acid
  8. ^ FDA GRAS Database. Succinic acid in the FDA SCOGS Database
  9. ^ http://drugtopics.modernmedicine.com/drugtopics/Drugtopics.com+Exclusives/Overview-of-pharmaceutical-excipients-used-in-tabl/ArticleStandard/Article/detail/561047
  10. ^ Lachman, Leon; Joseph B. Schwartz (1990). Pharmaceutical Dosage Forms--tablets. p. 288. ISBN 9780824780449. 
  11. ^ Peynaud, Emile (1984) Knowing and Making Wine.
  12. ^ "Succinic Acid MSDS" (PDF). BioAmber Inc. 


External links

Template:Citric acid cycle

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