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 | |
---|
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 | (e)-2-Butenedioate | Generator | trans-1,2-Ethylenedicarboxylate | Generator | trans-But-2-enedioate | Generator | trans-Butenedioate | Generator | Fumarate | 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 | HMDB | Mafusol | HMDB | Fumaric acid | HMDB | (2e)-2-Butenedioate | Generator | (E)-2-Butenedioate | biospider | (E)-2-Butenedioic acid, 9CI | db_source | 2-(E)-Butenedioate | biospider | 2-(E)-Butenedioic acid | biospider | 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 | |
---|
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 | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: Environmental role: Industrial application: |
---|
Physico-Chemical Properties - Experimental |
---|
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 |
---|
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 | 10197150 |
---|
ChEMBL ID | CHEMBL503160 |
---|
KEGG Compound ID | C00122 |
---|
Pubchem Compound ID | 444972 |
---|
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 | CVQ85-P:CVQ85-P |
---|
EAFUS ID | 1403 |
---|
Dr. Duke ID | FUMARIC-ACID |
---|
BIGG ID | 33938 |
---|
KNApSAcK ID | C00001183 |
---|
HET ID | FUM |
---|
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 | |
---|
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.
|
---|