Muconic acid explained

Muconic acid should not be confused with meconic acid.

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-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.

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.^[4]

See also

• Dicarboxylic acid
• 2-Aminomuconic acid

Notes

1. Wiwanitkit V, Soogarun S, Suwansaksri J . 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 . 2007 . 17366320 . 10.1080/01926230601156278. 6392962 .
2. Weaver VM, Davoli CT, Heller PJ, etal . Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels . Environ. Health Perspect. . 104 . 3 . 318–23 . 1996 . 8919771 . 10.2307/3432891 . 1469300 . 3432891 . Brogan &#38.
3. Organic Syntheses. 26. 1946. P. C. Guha . D. K. Sankaran . Muconic Acid. 57–60 . 10.15227/orgsyn.026.0057. 20280761 .
4. Curran KA, Leavitt JM, Karim AS, Alper HS. Metabolic engineering of muconic acid production in Saccharomyces cerevisiae.. Metab. Eng.. 23164574. 10.1016/j.ymben.2012.10.003. 15. 2013. 55–66.