Showing Metabocard for mesaconate (BASm0002023)
| Common Name | Mesaconate |
|---|---|
| Description | Mesaconic acid, also known as 2-methylfumarate or citronic 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. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate. |
| Structure | |
| Molecular Formula | C5H6O4 |
| Average Mass | 130.09870 |
| Monoisotopic Mass | 130.02661 |
| IUPAC Name | (2E)-2-methylbut-2-enedioic acid |
| Traditional Name | Mesaconic acid |
| CAS Registry Number | 498-24-8 |
| SMILES | C/C(=C\C(=O)[O-])C(=O)[O-] |
| InChI Identifier | InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ |
| InChI Key | HNEGQIOMVPPMNR-NSCUHMNNSA-N |
| CHEBI ID | CHEBI:36986 |
| HMDB ID | HMDB0000749 |
| State | Solid |
| Water Solubility | 1.59e+01 g/l |
| logP | 0.21 |
| logS | -0.91 |
| pKa (Strongest Acidic) | 3.72 |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 74.6 Ų |
| Rotatable Bond Count | 2 |
| Physiological Charge | -2 |
| Formal Charge | 0 |
| Refractivity | 28.96 m³·mol⁻¹ |
| Polarizability | 11.24 |