FComEx: Succinic acid (PC000110)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:30 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000110

FoodDB Record

FDB001931

Chemical Information

Name

Succinic acid

Description

Succinic 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 Number

110-15-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,2-Ethanedicarboxylate	biospider
1,2-Ethanedicarboxylic acid	biospider
1,4-Butanedioate	biospider
1,4-Butanedioic acid	biospider
1,4-BUTANEDIOIC ACID (SUCCINIC ACID)	biospider
1cze	biospider
Acid of amber	biospider
Acide butanedioique	ChEBI
Acide succinique	ChEBI
Acidum succinicum	biospider
Amber acid	db_source
Amber acid, butanedioic acid, ethylenesuccinic acid	biospider
Ammonium succinate	biospider
Asuccin	biospider
Bernsteinsaeure	ChEBI
Butandisaeure	ChEBI
Butanedioic acid	biospider
Butanedioic acid (9CI)	biospider
Butanedioic acid diammonium salt	biospider
Butanedioic acid, 9CI	db_source
Butanedionate	Generator
Butanedionic acid	biospider
Dihydrofumarate	biospider
Dihydrofumaric acid	biospider
E363	db_source
Ethane-1,2-dicarboxylic acid	db_source
Ethanedicarboxylic acid	biospider
Ethylene dicarboxylic acid	biospider
Ethylene succinic acid	biospider
Ethylenesuccinate	Generator
Ethylenesuccinic acid	biospider
FMR	biospider
HOOC-CH2-CH2-COOH	biospider
Katasuccin	biospider
MAE	biospider
Potassium succinate	biospider
Sal succini	biospider
Salt of amber	biospider
SIN	biospider
Spirit of amber	biospider
SUC	biospider
SUCC	biospider
Succinate	biospider
succinate, 9	biospider
Succinellite	biospider
Succinic acid (8CI)	biospider
Succinic acid, acs	biospider
Succinicum acidum	biospider
Succinicun acidum	biospider
Wormwood	biospider
Wormwood acid	db_source

Chemical Formula

C4H6O4

IUPAC name

butanedioic acid

InChI Identifier

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI Key

KDYFGRWQOYBRFD-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCC(O)=O

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents