ContaminantDB: Succinic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (41)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:23 UTC

Update Date

2026-04-16 21:17:42 UTC

Accession Number

CHEM003413

Identification

Common Name

Succinic acid

Class

Small Molecule

Description

Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. 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. Succinate is commonly used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Succinate plays a role in the citric acid cycle, an energy-yielding process and is metabolized by succinate dehydrogenase to fumarate. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds 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 whole Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e.g. malate. (1) Mutations in the four genes encoding the subunits of succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (2). Succinate also acts as an oncometabolite. Succinate inhibits 2-oxoglutarate-dependent histone and DNA demethylase enzymes, resulting in epigenetic silencing that affects neuroendocrine differentiation.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Dietary Supplement
Drug
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

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

Synonyms

Value	Source
1,2-Ethanedicarboxylic acid	ChEBI
Acide butanedioique	ChEBI
Acide succinique	ChEBI
Acidum succinicum	ChEBI
Amber acid	ChEBI
Asuccin	ChEBI
Bernsteinsaeure	ChEBI
Butandisaeure	ChEBI
Butanedionic acid	ChEBI
Dihydrofumaric acid	ChEBI
e363	ChEBI
Ethylenesuccinic acid	ChEBI
HOOC-CH2-CH2-COOH	ChEBI
Spirit OF amber	ChEBI
1,2-Ethanedicarboxylate	Generator
Butanedionate	Generator
Dihydrofumarate	Generator
Ethylenesuccinate	Generator
Succinate	Generator
1,2 Ethanedicarboxylic acid	MeSH
1,4 Butanedioic acid	MeSH
1,4-Butanedioic acid	MeSH
Ammonium succinate	MeSH
Butanedioic acid	MeSH
Potassium succinate	MeSH
Succinate, ammonium	MeSH
Succinate, potassium	MeSH
1,4-Butanedioate	HMDB
Katasuccin	HMDB
Wormwood acid	HMDB
2-Acetamido-2-deoxy-D-glucose	ChEBI, HMDB
D-GlcNAc	ChEBI, HMDB
N-Acetyl-D-glucosamine	ChEBI, HMDB
N-Acetylchitosamine	ChEBI, HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB

Chemical Formula

C₄H₆O₄

Average Molecular Mass

118.088 g/mol

Monoisotopic Mass

118.027 g/mol

CAS Registry Number

110-15-6

IUPAC Name

butanedioic acid

Traditional Name

succinic acid

SMILES

OC(=O)CCC(O)=O

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

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

Fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:15741 )
alpha,omega-dicarboxylic acid (CHEBI:15741 )
Dicarboxylic acids (LMFA01170043 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

All Tissues

Pathways

Name	SMPDB Link	KEGG Link
Carnitine Synthesis	SMP00465	Not Available
Citric Acid Cycle	SMP00057	map00020
Glutamate Metabolism	SMP00072	map00250
Mitochondrial Electron Transport Chain	SMP00355	map00190
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Pyruvate Carboxylase Deficiency	SMP00350	Not Available
Apoptosis	Not Available	map04210
Oxidative phosphorylation	Not Available	map00190
Insulin secretion	Not Available	map04911
Renin-angiotensin system	Not Available	map04614
Metabolic Pathways	Not Available	Not Available
Histidine Metabolism	SMP00044	map00340
Benzoate Degradation	Not Available	Not Available
Cell cycle	Not Available	map04110
Pentose Phosphate Pathway	SMP00031	map00030
Vitamin B6 Metabolism	SMP00017	map00750
Aminoglycosides	Not Available	Not Available
Tyrosine Metabolism	SMP00006	map00350
Butanoate metabolism	Not Available	map00650
Bile secretion	Not Available	map04976

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystalline powder

Experimental Properties

Property	Value
Melting Point	184°C
Boiling Point	235°C
Solubility	58 g/L

Predicted Properties

Property	Value	Source
Water Solubility	211 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-0.4	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	23.54 m³·mol⁻¹	ChemAxon
Polarizability	10.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-0920000000-f286e6204a4163b823ba	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00c1-3930000000-3cc18e719822b5af661a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-93b4807ae6275a3e59d7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kos-9100000000-f1df0903a24c305e68ec	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0910000000-300c33b39fb991b5a73e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-f286e6204a4163b823ba	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-bf336910bb37d7f78140	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9800000000-df5ff4e8457d2d4ef919	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00c1-3930000000-3cc18e719822b5af661a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-f838d863ee7c2b111f02	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-9300000000-f0644daf4fbb11fcc2dc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-9710000000-ff8325384b9eefd19106	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9300000000-f9dc864d93a09d3074f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9300000000-76c151de384928b2256f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-01b9-7900000000-51d2341c097f04827944	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-004i-9000000000-93b4807ae6275a3e59d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dj-0971010000-37d214dc7a8fdc26116b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-249222ac742c1634cec9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-9000000000-6897d49472dba6a34a27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0490000000-d138f8023125921b4b82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-1900000000-4ffdabe5bde527b66982	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9100000000-c20baa818f5ff5f678c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-7a49a18aa6fcb2540a12	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00di-9000000000-7e1f195f111b4eafb4fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9400000000-e50afc90e20cd420ba9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00xr-9600000000-43167f2549cbb5d5f7e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-4ffdabe5bde527b66982	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9100000000-7a8bfa543dc087bea06d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-fdec6c7458176f3cbeb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9955aeb0e5a9f88ae70e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-2900000000-9d959a53833b07094158	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l6r-9600000000-c367e11e737714d41418	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-e65aa602a8293debec36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e1f840494c9003279869	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7900000000-1089efd4a3469bcf14f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0604-9000000000-0e0e60bb202ffb004894	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05di-9100000000-c629bea41d0d3d896425	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Eye contact, Inhalation, Ingestion.

Mechanism of Toxicity

Succinate can inhibit the activities of α-KG–dependent oxygenases (KDMs) and the TET family of 5-methlycytosine (5mC) hydroxylases. Succinate also mediates allosteric inhibition of hypoxia inducible factor (HIF) prolyl hydroxylases (PHDs). Inhibition of HIF PHDs leads to activation of HIF-mediated pseudohypoxic response, whereas inhibition of KDMs and TET family of 5mC hydroxylases causes epigenetic alterations that ultimately cause cancer. Succination of KEAP1 in FH deficiency results in the constitutive activation of the antioxidant defense pathway mediated by NRF2, conferring a reductive milieu that promotes cell proliferation. Succination of the Krebs cycle enzyme Aco2 impairs aconitase activity in Fh1-deficient MEFs. Succination also causes irreversible inactivation of glyceraldehyde-3-phosphate dehydrogenase (GAPDH).

Metabolism

Succinic acid can be converted into fumaric acid by oxidation via succinate dehydrogenase.

Toxicity Values

Acute oral toxicity (LD50): 2260 mg/kg [Rat].

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. Has been implicated in oncogenesis (17).

Uses/Sources

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. It is also sold as a food additive and dietary supplement, and is generally recognized as safe by the US FDA.

Minimum Risk Level

Not Available

Health Effects

At acute doses or exposures succinic acid is a skin irritant. Chronically high doses of succinate can lead to succinylation or succination of a variety of enzymes. Partial succinate dehydrogenase deficiency (15% to 50% of normal reference enzyme activity) in skeletal muscle leads to elevated succinate levels and causes mitochondrial myopathy with various symptoms, for example, brain involvement, cardiomyopathy, and/or exercise intolerance.

Symptoms

Acute Exposure: the clinical signs of acute toxicity are weakness and diarrhea.

Treatment

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Concentrations

Not Available

External Links

DrugBank ID

DB00139

HMDB ID

HMDB0000254

FooDB ID

FDB001931

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001205

BiGG ID

Not Available

BioCyc ID

SUC

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Michael Diamantoglou, Gerhard Meyer, “Process for the production of water-insoluble fibers of cellulose monoesters of maleic acid, succinic acid and phthalic acid, having an extremely high absorbability for water and physiological liquids.” U.S. Patent US4734239, issued April, 1941.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666

2. Berglund, Kris Arvid; Andersson, Christian; Rova, Ulrika. Process for the production of succinic acid. PCT Int. Appl. (2007), 30pp.

3. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.

4. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.

5. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.

6. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.

7. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386

8. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

9. Berglund, Kris Arvid; Andersson, Christian; Rova, Ulrika. Process for the production of succinic acid. PCT Int. Appl. (2007), 30pp.