Record Information
Version1.0
Creation date2015-10-09 22:28:30 UTC
Update date2017-01-19 02:36:13 UTC
FoodComEx IDPC000110
FoodDB RecordFDB001931
Chemical Information
NameSuccinic acid
DescriptionSuccinic acid is a four-carbon acyclic dicarboxylic acid. It is a white, odorless solid with a highly acidic taste. It is used as a flavoring agent, contributing a sour and astringent component characteristic of the umami taste (PMID:21932253). The anion, succinate, is a key component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in mitochondrial function, being both part of the respiratory chain and the Krebs cycle. SDH, with a covalently attached FAD prosthetic group, is able to bind several different enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the entire Krebs cycle. Succinic acid has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid is also a microbial metabolite. Indeed, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter sp., Acinetobacter sp., Proteus mirabilis, Citrobactes frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid, or its anion succinate, is used as an excipient in pharmaceutical products to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. In 2004, succinic acid was identified by the Department of Energy of the United States of America as one of twelve molecules that can be produced from plant sugars through biological or chemical processes and that have a potential to subsequently be converted to a number of high-value bio-based chemicals or materials.
CAS Number110-15-6
Structure
Thumb
Synonyms
SynonymSource
1,2-Ethanedicarboxylatebiospider
1,2-Ethanedicarboxylic acidbiospider
1,4-Butanedioatebiospider
1,4-Butanedioic acidbiospider
1,4-BUTANEDIOIC ACID (SUCCINIC ACID)biospider
1czebiospider
Acid of amberbiospider
Acide butanedioiqueChEBI
Acide succiniqueChEBI
Acidum succinicumbiospider
Amber aciddb_source
Amber acid, butanedioic acid, ethylenesuccinic acidbiospider
Ammonium succinatebiospider
Asuccinbiospider
BernsteinsaeureChEBI
ButandisaeureChEBI
Butanedioic acidbiospider
Butanedioic acid (9CI)biospider
Butanedioic acid diammonium saltbiospider
Butanedioic acid, 9CIdb_source
ButanedionateGenerator
Butanedionic acidbiospider
Dihydrofumaratebiospider
Dihydrofumaric acidbiospider
E363db_source
Ethane-1,2-dicarboxylic aciddb_source
Ethanedicarboxylic acidbiospider
Ethylene dicarboxylic acidbiospider
Ethylene succinic acidbiospider
EthylenesuccinateGenerator
Ethylenesuccinic acidbiospider
FMRbiospider
HOOC-CH2-CH2-COOHbiospider
Katasuccinbiospider
MAEbiospider
Potassium succinatebiospider
Sal succinibiospider
Salt of amberbiospider
SINbiospider
Spirit of amberbiospider
SUCbiospider
SUCCbiospider
Succinatebiospider
succinate, 9biospider
Succinellitebiospider
Succinic acid (8CI)biospider
Succinic acid, acsbiospider
Succinicum acidumbiospider
Succinicun acidumbiospider
Wormwoodbiospider
Wormwood aciddb_source
Chemical FormulaNot Available
IUPAC nameNot Available
InChI IdentifierInChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI KeyKDYFGRWQOYBRFD-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC(O)=O
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.59HANSCH,C ET AL. (1995)
Experimental Water Solubility83.2 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Melting PointMp 184-185°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci I847
Glentham GK9938
MetaSci HMDB0000254
Sigma-Aldrich HMDB0000254
Toronto Research Chemicals S688765