| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:35:58 UTC |
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| Update Date | 2020-05-05 18:37:19 UTC |
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| BMDB ID | BMDB0000749 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Mesaconic acid |
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| Description | Citraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Citraconic acid exists in all living organisms, ranging from bacteria to humans. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (e)-2-Methyl-2-butenedioic acid | ChEBI | | (e)-Citraconic acid | ChEBI | | 2-Methylfumaric acid | ChEBI | | Citronic acid | ChEBI | | Methylfumaric acid | ChEBI | | trans-1-Propene-1,2-dicarboxylic acid | ChEBI | | trans-2-Methyl-2-butenedioic acid | ChEBI | | 2-Methylfumarate | Kegg | | (e)-2-Methyl-2-butenedioate | Generator | | (e)-Citraconate | Generator | | Citronate | Generator | | Methylfumarate | Generator | | trans-1-Propene-1,2-dicarboxylate | Generator | | trans-2-Methyl-2-butenedioate | Generator | | Mesaconate | Generator | | (Z)-2-Methyl-2-butenedioic acid | HMDB | | Citraconic acid | HMDB | | Citraconic acid, (e)-isomer | HMDB | | Citraconic acid, ammonium salt | HMDB | | Citraconic acid, calcium salt | HMDB | | Citraconic acid, sodium salt | HMDB | | Methylmaleic acid | HMDB | | Monomethylfumarate | HMDB | | (2E)-2-Methyl-2-butenedioate | HMDB | | (2E)-2-Methyl-2-butenedioic acid | HMDB |
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| Chemical Formula | C5H6O4 |
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| Average Molecular Weight | 130.0987 |
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| Monoisotopic Molecular Weight | 130.02660868 |
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| IUPAC Name | (2E)-2-methylbut-2-enedioic acid |
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| Traditional Name | mesaconic acid |
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| CAS Registry Number | 498-24-8 |
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| SMILES | C\C(=C/C(O)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ |
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| InChI Key | HNEGQIOMVPPMNR-NSCUHMNNSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Methyl-branched fatty acids |
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| Alternative Parents | |
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| Substituents | - Methyl-branched fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- 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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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 200 - 202 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 26.3 mg/mL at 18 °C | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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