Muconic acid
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Overview
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 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.[1][2] Synthetically, trans,trans-muconic acid can be prepared from adipic acid.[3]
cis,cis-Muconic acid is produced by some bacteria by the enzymatic degradation of various aromatic chemical compounds.
See also
- Dicarboxylic acid
- Meconic acid, an unrelated dicarboxylic acid
- 2-Aminomuconic acid
References
- ↑ 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:10.1080/01926230601156278. 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