Showing Metabocard for cis,cis-muconate (BASm0001835)
| Common Name | Cis,cis-muconate |
|---|---|
| Description | cis-cis-Muconic acid is a presumptive metabolite of benzene. Muconic acid was first isolated from the urine of rabbits and dogs in 1909 (M. Jaffe, Z Physiol Chem 62:58-67). It was originally thought that if muconic acid was formed by the opening of the benzene ring in vivo then the cis-cis isomer should be the initial (and primary) product. However subsequent studies conducted in the 1950s proved that trans-trans-muconic acid is a true metabolite of benzene in mammals (Parke DV, Williams RT. Biochem J 51:339-348 (1952)). Furthermore, dosing rabbits with phenol or catechol also resulted in the urinary excretion of trans-trans-muconic acid. The oxidative ring opening of benzene first gives rise to cis-cis-muconaldehyde, which then isomerizes to cis-trans- and trans-trans-muconaldehyde; the latter is oxidized in vivo to trans-trans-muconic acid. Isomerization of the trans-trans form may take place in vivo to yield small amounts if the cis-cis and cis-trans form of muconic acid. cis-cis-Muconic acid may also be generated from microbial fermentation of benzoic acid. Certain strains of arthobacter are particularly efficient at this process. cis-cis-Muconic acid can also be found in Pseudomonas and Escherichia coli (https://link.springer.com/article/10.1007/BF00250491) (PMID:26360870 ). |
| Structure | |
| Molecular Formula | C6H6O4 |
| Average Mass | 142.10940 |
| Monoisotopic Mass | 142.02661 |
| IUPAC Name | (2Z,4Z)-hexa-2,4-dienedioic acid |
| Traditional Name | Muconic acid |
| CAS Registry Number | 1119-72-8 |
| SMILES | O=C([O-])/C=C\C=C/C(=O)[O-] |
| InChI Identifier | InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2- |
| InChI Key | TXXHDPDFNKHHGW-CCAGOZQPSA-N |
| CHEBI ID | CHEBI:32379 |
| HMDB ID | HMDB0006331 |
| State | Solid |
| Water Solubility | 3.48e+00 g/l |
| logP | 0.67 |
| logS | -1.61 |
| pKa (Strongest Acidic) | 3.87 |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 74.6 Ų |
| Rotatable Bond Count | 3 |
| Physiological Charge | -2 |
| Formal Charge | 0 |
| Refractivity | 34.93 m³·mol⁻¹ |
| Polarizability | 12.58 |