Succinic acid

Succinic acid
Names
Preferred IUPAC name
Butanedioic acid[1]
Other names
Succinic acid[1]
1,4-Butanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.402 Edit this at Wikidata
E number E363 (antioxidants, ...)
UNII
  • InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) checkY
    Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
    Key: KDYFGRWQOYBRFD-UHFFFAOYAC
  • C(CC(=O)O)C(=O)O
Properties
C4H6O4
Molar mass 118.088 g·mol−1
Density 1.56 g/cm3[2]
Melting point 184–190 °C (363–374 °F; 457–463 K)[2][4]
Boiling point 235 °C (455 °F; 508 K)[2]
58 g/L (20 °C)[2] or 100 mg/mL[3]
Solubility in Methanol 158 mg/mL[3]
Solubility in Ethanol 54 mg/mL[3]
Solubility in Acetone 27 mg/mL[3]
Solubility in Glycerol 50 mg/mL[3]
Solubility in Ether 8.8 mg/mL[3]
Acidity (pKa) pKa1 = 4.2
pKa2 = 5.6
-57.9·10−6 cm3/mol
Hazards
Flash point 206 °C (403 °F; 479 K)[2]
Related compounds
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).
checkY verify (what is checkY☒N ?)

Succinic acid (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2.[5] In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.[6]

Succinate is generated in mitochondria via the tricarboxylic acid (TCA) cycle. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling.[6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function.

Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury.[6][7][8]

Succinic acid is marketed as food additive E363. The name derives from Latin succinum, meaning amber.

  1. ^ a b "CHAPTER P-6. Applications to Specific Classes of Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 747. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ a b c d e f "Product Information Sheet: Succinic Acid" (PDF). Sigma Aldrich. Archived from the original (PDF) on 7 November 2017. Retrieved 7 November 2015.
  4. ^ Chikhalia, V.; Forbes, R.T.; Storey, R.A.; Ticehurst, M. (January 2006). "The effect of crystal morphology and mill type on milling induced crystal disorder". European Journal of Pharmaceutical Sciences. 27 (1): 19–26. doi:10.1016/j.ejps.2005.08.013. ISSN 0928-0987. PMID 16246535.
  5. ^ Cite error: The named reference Toxnet was invoked but never defined (see the help page).
  6. ^ a b c Cite error: The named reference Tretter2016rev was invoked but never defined (see the help page).
  7. ^ Mills, Evanna; O'Neill, Luke A.J. (May 2014). "Succinate: a metabolic signal in inflammation". Trends in Cell Biology. 24 (5): 313–320. doi:10.1016/j.tcb.2013.11.008. hdl:2262/67833. PMID 24361092.
  8. ^ Cite error: The named reference Chouchani was invoked but never defined (see the help page).