AFCDB: 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

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Physico-Chemical Properties - Experimental

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

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	2014-09-20	View Spectrum
GC-MS	fumarate, 2 TMS, GC-MS Spectrum	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	fumarate, 2 TMS, GC-MS Spectrum	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	fumarate, 2 TMS, GC-MS Spectrum	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	fumarate, 2 TMS, GC-MS Spectrum	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	fumarate, 2 TMS, GC-MS Spectrum	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-9100000000-2cf649749b42cc0c610c	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0007-0890000000-b1c35cd55deb81254f66	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	fumarate, non-derivatized, GC-MS Spectrum	splash10-0002-0940000000-177fdb9168659029ffaa	Spectrum
Predicted GC-MS	fumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	Spectrum
Predicted GC-MS	fumarate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	Spectrum
Predicted GC-MS	fumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	fumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	fumarate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	fumarate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	fumarate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-04b277f233e1bd56c9af	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4900000000-99764eff7d7cb7bfaee3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-453b921a0aaf64cfd558	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9000000000-cd7e7026d13bb5fe844b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-9000000000-383c22a29e2769626c47	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ir3-9000000000-3013847e2e0f9bf18d29	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-9cc4f29b523ed34dc0b6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00di-9000000000-d9885a6093f38dd8b9fa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-9000000000-46fdee94b5a787f1b81f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03k9-8900000000-3ff0fb725ec9dffc3688	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014m-9000000000-394fd8f1b59c7befec9d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-3d34cd791255c022876a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-55a5c43ec34fdd2cb0a4	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9000000000-7c9639a65d534cd8ff97	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-9000000000-c5eb63dc643f72e91ede	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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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
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	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
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

Showing 1 to 7 of 7 entries

Enzymes

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Showing 1 to 3 of 3 entries

Pathways

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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

Showing 1 to 7 of 7 entries

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Showing 1 to 2 of 2 entries

Files

MSDS

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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.

Fumaric acid (FDB003291)

Structure for FDB003291 (Fumaric acid)