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.
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