Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:44 UTC |
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Update date | 2019-11-26 02:58:50 UTC |
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Primary ID | FDB003291 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Fumaric acid |
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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. |
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CAS Number | 110-17-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(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 |
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Predicted Properties | |
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Chemical Formula | C4H4O4 |
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IUPAC name | (2E)-but-2-enedioic acid |
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InChI Identifier | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- |
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InChI Key | VZCYOOQTPOCHFL-UPHRSURJSA-N |
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Isomeric SMILES | OC(=O)\C=C/C(O)=O |
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Average Molecular Weight | 116.0722 |
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Monoisotopic Molecular Weight | 116.010958616 |
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Classification |
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Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Environmental role: Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 41.39%; H 3.47%; O 55.14% | DFC |
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Melting Point | Mp 300-302° (sealed tube) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 7 mg/mL at 25 oC | US EPA (1981) |
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Experimental logP | 0.46 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 4.54 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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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 |
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MS/MS | Type | Description | Splash Key | View |
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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 |
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NMR | Type | Description | | View |
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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 |
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External Links |
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ChemSpider ID | 10197150 |
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ChEMBL ID | CHEMBL503160 |
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KEGG Compound ID | C00122 |
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Pubchem Compound ID | 444972 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18012 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01677 |
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HMDB ID | HMDB00134 |
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CRC / DFC (Dictionary of Food Compounds) ID | CVQ85-P:CVQ85-P |
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EAFUS ID | 1403 |
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Dr. Duke ID | FUMARIC-ACID |
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BIGG ID | 33938 |
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KNApSAcK ID | C00001183 |
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HET ID | FUM |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1024321 |
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SuperScent ID | 444972 |
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Wikipedia ID | Fumaric acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Acidulant | 64047 | A substance that increases acidity, commonly used as a food additive. Biologically, it helps maintain pH balance. Therapeutically, acidulants have applications in managing digestive issues and nutrient absorption. Key medical uses include treating conditions like gastroesophageal reflux disease (GERD) and enhancing mineral absorption, particularly in patients with malabsorption disorders. | DUKE | Anti dermatitic | 50177 | An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling. | DUKE | Anti hepatocarcinogenic | 35610 | An agent that prevents or inhibits the development of liver cancer, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to reduce the risk of hepatocellular carcinoma, commonly used in managing liver disease and cancer. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-psoriac | 52217 | An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Name | 48318 | flavor | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Fumarate hydratase, mitochondrial | FH | P07954 | Argininosuccinate lyase | ASL | P04424 | Adenylosuccinate lyase | ADSL | P30566 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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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.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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