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. Its name is derived from mucic acid.
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.[4][5] Synthetically, trans,trans-muconic acid can be prepared from adipic acid.[6]
cis,cis-Muconic acid is produced by some bacteria by the enzymatic degradation of various aromatic chemical compounds.
The bioproduction of muconic acid is of interest because of its potential use as a platform chemical for the production of several valuable consumer bioplastics including nylon-6,6, polyurethane, and polyethylene terephthalate.[7]
See also
Notes
- ^ Merck Index, 11th Edition, 6210
- ^ Muconic acid at Sigma-Aldrich
- ^ Merck Index, 12th Edition (1996), 6381, p.1079
- ^ 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. S2CID 6392962.
- ^ 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). Brogan &: 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC 1469300. PMID 8919771.
- ^ P. C. Guha; D. K. Sankaran (1946). "Muconic Acid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761.
- ^ Curran KA, Leavitt JM, Karim AS, Alper HS (2013). "Metabolic engineering of muconic acid production in Saccharomyces cerevisiae". Metab. Eng. 15: 55–66. doi:10.1016/j.ymben.2012.10.003. PMID 23164574.