Muconic acid
From Wikipedia, the free encyclopedia
| trans,trans-Muconic acid[1][2] | |
|---|---|
 |
|
| IUPAC name | (2E,4E)-Hexa-2,4-dienedioic acid |
| Other names | (E,E)-Muconic acid |
| Identifiers | |
| CAS number | [3588-17-8] |
| PubChem | |
| SMILES | OC(\C=C/C=C\C(O)=O)=O |
| Properties | |
| Molecular formula | C6H6O4 |
| Molar mass | 142.11 g/mol |
| Appearance | Crystalline prisms |
| Melting point |
290 °C |
| Boiling point |
320 °C |
| Solubility in water | 1 g/5 L at 15 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Muconic acid is a dicarboxylic acid. There are three isomeric forms designated trans,trans-muconic acid, cis,trans-muconic acid, and cis,cis-muconic acid which differ by the geometry around the double bonds.
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trans,trans cis,trans cis,cis
trans,trans-Muconic acid is a metabolite of benzene in humans. The determination of its concentration in urine is therefore used as a biomarker of occupational or environmental exposure to benzene.[3][4] Synthetically, trans,trans-muconic acid can be prepared from adipic acid.[5]
cis,cis-Muconic acid is produced by some bacteria by the enzymatic degradation of various aromatic chemical compounds.
[edit] See also
- Dicarboxylic acid
- Meconic acid, an unrelated dicarboxylic acid
- 2-Aminomuconic acid
[edit] References
- ^ Merck Index, 11th Edition, 6210.
- ^ trans,trans-Muconic acid at Sigma-Aldrich
- ^ Wiwanitkit V, Soogarun S, Suwansaksri J (2007). "A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure". Toxicologic pathology 35 (2): 268–9. doi:. PMID 17366320.
- ^ Weaver VM, Davoli CT, Heller PJ, et al (1996). "Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels". Environ. Health Perspect. 104 (3): 318–23. PMID 8919771.
- ^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
