Record Information |
---|
Version | 1.0 |
---|
Creation date | 2015-05-07 20:19:52 UTC |
---|
Update date | 2020-09-17 15:38:22 UTC |
---|
Primary ID | FDB030865 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | fumarate |
---|
Description | Fumaric acid, also known as E297 or fumarsaeure, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans. Within humans, fumaric acid participates in a number of enzymatic reactions. In particular, fumaric acid can be biosynthesized from L-malic acid; which is catalyzed by the enzyme fumarate hydratase, mitochondrial. In addition, fumaric acid can be biosynthesized from succinic acid through the action of the enzyme mutant succinate dehydrogenase. A butenedioic acid in which the C=C double bond has E geometry. In humans, fumaric acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Fumaric acid is an odorless and sour tasting compound. Outside of the human body, Fumaric acid is found, on average, in the highest concentration within a few different foods, such as sweet cherries, star fruits, and milk (cow) and in a lower concentration in grape wines. Fumaric acid has also been detected, but not quantified in, several different foods, such as cow milks, apples, fishes, garden rhubarbs, and common sages. This could make fumaric acid a potential biomarker for the consumption of these foods. Fumaric acid is a potentially toxic compound. Fumaric acid, with regard to humans, has been found to be associated with several diseases such as rheumatoid arthritis, eosinophilic esophagitis, and lung cancer; fumaric acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and fumarase deficiency. |
---|
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 |
|
---|
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-OWOJBTEDSA-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 |
---|
|
Physiological effect | Health effect: |
---|
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 | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | Not Available | |
---|
Melting Point | Not Available | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
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 | 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 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0229-9600000000-cd9e2979d0bb1e2a62f2 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-03k9-8900000000-dc50dbf8a50872383d54 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0002-9100000000-b47e534bc82a6ed36e7c | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-04b277f233e1bd56c9af | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03di-4900000000-99764eff7d7cb7bfaee3 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00di-9000000000-453b921a0aaf64cfd558 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9000000000-cd7e7026d13bb5fe844b | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00dj-9000000000-383c22a29e2769626c47 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0ir3-9000000000-3013847e2e0f9bf18d29 | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-00di-9000000000-9cc4f29b523ed34dc0b6 | Spectrum | MS/MS | LC-MS/MS Spectrum - 15V, Negative | splash10-00di-9000000000-d9885a6093f38dd8b9fa | Spectrum | MS/MS | LC-MS/MS Spectrum - 45V, Negative | splash10-00di-9000000000-46fdee94b5a787f1b81f | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-03k9-8900000000-3ff0fb725ec9dffc3688 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014m-9000000000-394fd8f1b59c7befec9d | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-9800000000-dbf34563376daeb2901f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00xs-9200000000-113bf08cdc77707ed3ad | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00fr-9000000000-f32d7ec65e8649bc2b0a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-408d53a9fff7acc8ca23 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-6900000000-f149e9e5a34e27dd4d4e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fxt-9000000000-cae5f71dc27daaf17d9e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-3d34cd791255c022876a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-55a5c43ec34fdd2cb0a4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uk9-9000000000-7c9639a65d534cd8ff97 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-9000000000-c5eb63dc643f72e91ede | Spectrum |
|
---|
NMR | |
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | Not Available |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
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 | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|