Succinic acid

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Succinic acid
Bernsteinsäure2.svg
Succinic-acid-3D-balls.png
Sample of succinic acid.jpg
Identifiers
CAS number110-15-6 YesY
PubChem1110
ChemSpider1078 YesY
UNIIAB6MNQ6J6L YesY
DrugBankDB00139
ChEBICHEBI:15741 YesY
ChEMBLCHEMBL576 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H6O4
Molar mass118.09 g mol−1
Density1.56 g/cm3[1]
Melting point184 °C (363 °F; 457 K)[1]
Boiling point235 °C (455 °F; 508 K)[1]
Solubility in water58 g/L (20 °C)[1]
Acidity (pKa)pKa1 = 4.2
pKa2 = 5.6
Hazards
Flash point206 °C (403 °F; 479 K)[1]
Related compounds
Other anionssodium succinate
Related carboxylic acidspropionic acid
malonic acid
butyric acid
malic acid
tartaric acid
fumaric acid
valeric acid
glutaric acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
 
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Succinic acid
Bernsteinsäure2.svg
Succinic-acid-3D-balls.png
Sample of succinic acid.jpg
Identifiers
CAS number110-15-6 YesY
PubChem1110
ChemSpider1078 YesY
UNIIAB6MNQ6J6L YesY
DrugBankDB00139
ChEBICHEBI:15741 YesY
ChEMBLCHEMBL576 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H6O4
Molar mass118.09 g mol−1
Density1.56 g/cm3[1]
Melting point184 °C (363 °F; 457 K)[1]
Boiling point235 °C (455 °F; 508 K)[1]
Solubility in water58 g/L (20 °C)[1]
Acidity (pKa)pKa1 = 4.2
pKa2 = 5.6
Hazards
Flash point206 °C (403 °F; 479 K)[1]
Related compounds
Other anionssodium succinate
Related carboxylic acidspropionic acid
malonic acid
butyric acid
malic acid
tartaric acid
fumaric acid
valeric acid
glutaric acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Succinic acid (/səkˈsɪnɨk/; IUPAC systematic name: butanedioic acid; historically known as spirit of amber) 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[edit]

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

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.[2] More recently, succinic acid is being produced through the fermentation of glucose from renewable feedstock and purification of raw bio-based succinic acid.[3]

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.[4]

Applications[edit]

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.[5] Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[6] 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.[7] As an excipient in pharmaceutical products it is used to control acidity[8] and, more rarely, in effervescent tablets.[9]

Biochemistry[edit]

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]

[[File:
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TCACycle_WP78go to articlego to articlego to articlego to articlego to HMDBgo to articlego to articlego to articleGo to articlego to articlego to articlego to articlego to articlego to articleGo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to HMDBgo to articlego to articlego to HMDBgo to articlego to articlego to HMDBgo to articlego to articlego to HMDBgo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to WikiPathwaysgo to articlego to articlego to articlego to article
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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[edit]

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.[10]

Succinates[edit]

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[edit]

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.[11]

See also[edit]

References[edit]

  1. ^ a b c d e Record in the GESTIS Substance Database from the IFA
  2. ^ Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523
  3. ^ "Life Cycle Analysis (LCA)". BioAmber Inc. 
  4. ^ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932), "Succinic Anhydride", Org. Synth. 12: 66 ; Coll. Vol. 2: 560 .
  5. ^ 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. 
  6. ^ NNFCC Renewable Chemicals Factsheet: Succinic Acid
  7. ^ FDA GRAS Database. Succinic acid in the FDA SCOGS Database
  8. ^ http://drugtopics.modernmedicine.com/drugtopics/Drugtopics.com+Exclusives/Overview-of-pharmaceutical-excipients-used-in-tabl/ArticleStandard/Article/detail/561047
  9. ^ Lachman, Leon; Joseph B. Schwartz (1990). Pharmaceutical Dosage Forms--tablets. p. 288. ISBN 9780824780449. 
  10. ^ Peynaud, Emile (1984) Knowing and Making Wine.
  11. ^ "Succinic Acid MSDS". BioAmber Inc. 


External links[edit]