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Muconic 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.

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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. Synthetically, trans,trans-muconic acid can be prepared from adipic acid.

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.

Notes

References

  1. ''Merck Index'', 11th Edition, '''6210'''
  2. [https://www.sigmaaldrich.com/US/en/product/aldrich/m90003 Muconic acid] at [[Sigma-Aldrich]]
  3. ''[[Merck Index]]'', 12th Edition (1996), 6381, p.1079
  4. (2007). "A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure". Toxicologic Pathology.
  5. (1996). "Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels". Brogan &#38.
  6. P. C. Guha. (1946). "Muconic Acid". Organic Syntheses.
  7. (2013). "Metabolic engineering of muconic acid production in Saccharomyces cerevisiae.". Metab. Eng..
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