Showing Compound Fumaric acid (FDB003291)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2019-11-26 02:58:50 UTC

Primary ID

FDB003291

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Fumaric acid

Description

Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit.

CAS Number

110-17-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-2-Butenedioic acid	ChEBI
(E)-2-Butenedioic acid	ChEBI
e297	ChEBI
Fumarsaeure	ChEBI
trans-1,2-Ethylenedicarboxylic acid	ChEBI
trans-But-2-enedioic acid	ChEBI
trans-Butenedioic acid	ChEBI
(2E)-2-Butenedioate	Generator
Fumarate	Generator
(E)-2-Butenedioate	Generator
trans-1,2-Ethylenedicarboxylate	Generator
trans-But-2-enedioate	Generator
trans-Butenedioate	Generator
(2E)-But-2-enedioate	HMDB
(2E)-But-2-enedioic acid	HMDB
2-(E)-Butenedioate	HMDB
2-(E)-Butenedioic acid	HMDB
Allomaleate	HMDB
Allomaleic acid	HMDB
Boletate	HMDB
Boletic acid	HMDB
FC 33	HMDB
Lichenate	HMDB
Lichenic acid	HMDB
trans-2-Butenedioate	HMDB
trans-2-Butenedioic acid	HMDB
Furamag	MeSH, HMDB
Mafusol	MeSH, HMDB
Fumaric acid	HMDB
(2e)-2-Butenedioate	Generator
(e)-2-Butenedioic acid	ChEBI
(E)-2-Butenedioic acid, 9CI	db_source
E297	db_source
FEMA 2488	db_source
Glaucic acid	db_source
Paramaleic acid	db_source
Toxilic acid	biospider
trans-Ethylene-1,2-dicarboxylic acid	db_source
Tumaric acid	biospider

Predicted Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	0.21	ALOGPS
logP	-0.041	ChemAxon
logS	-0.68	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	2	ChemAxon
Refractivity	24.61 m³·mol⁻¹	ChemAxon
Polarizability	9.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C4H4O4

IUPAC name

(2E)-but-2-enedioic acid

InChI Identifier

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

InChI Key

VZCYOOQTPOCHFL-UPHRSURJSA-N

Isomeric SMILES

OC(=O)\C=C/C(O)=O

Average Molecular Weight

116.0722

Monoisotopic Molecular Weight

116.010958616

Classification

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 acyl
Fatty acid
Unsaturated 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

butenedioic acid (CHEBI:18012 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Biological role:

Environmental role:

Air pollutant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.39%; H 3.47%; O 55.14%	DFC
Melting Point	Mp 300-302° (sealed tube)	DFC
Boiling Point	Not Available
Experimental Water Solubility	7 mg/mL at 25 oC	US EPA (1981)
Experimental logP	0.46	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 4.54 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

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)	splash10-0002-2940000000-e988056514d4ce4acc27	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2960000000-a5ebaf2bbade922838ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2950000000-32afa4d45e0e72b174b4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-3690000000-75089756992cdbe841e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9100000000-2cf649749b42cc0c610c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-0890000000-b1c35cd55deb81254f66	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2940000000-e988056514d4ce4acc27	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2960000000-a5ebaf2bbade922838ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2950000000-32afa4d45e0e72b174b4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-3690000000-75089756992cdbe841e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0940000000-177fdb9168659029ffaa	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18012

Phenol-Explorer ID

Not Available

DrugBank ID

DB01677

HMDB ID

HMDB00134

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1024321

SuperScent ID

444972

Wikipedia ID

Fumaric acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acidulant	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti hepatocarcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Fumarate hydratase, mitochondrial	FH	P07954
Argininosuccinate lyase	ASL	P04424
Adenylosuccinate lyase	ADSL	P30566

Pathways

Name	SMPDB Link	KEGG Link
Arginine and Proline Metabolism	SMP00020	map00330
Aspartate Metabolism	SMP00067	map00250
Citric Acid Cycle	SMP00057	map00020
Mitochondrial Electron Transport Chain	SMP00355	map00190
Phenylalanine and Tyrosine Metabolism	SMP00008	map00360
Tyrosine Metabolism	SMP00006	map00350
Urea Cycle	SMP00059	map00330

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sour	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Fumaric acid (FDB003291)

Structure for FDB003291 (Fumaric acid)