Muconic acid

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Muconic acid[1][2]
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Template:Longitem Template:Chembox Elements/molecular formula
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Appearance Crystalline prisms
Density 1.366 g/mL
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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.

Skeletal formula of trans,trans-muconic acid Skeletal formula of cis,trans-muconic acid Skeletal formula of cis,cis-muconic acid
Ball-and-stick model of the trans,trans-muconic acid molecule Ball-and-stick model of the cis,trans-muconic acid molecule Ball-and-stick model of the cis,cis-muconic acid molecule
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

  1. Merck Index, 11th Edition, 6210
  2. Muconic acid at Sigma-Aldrich
  3. Merck Index, 12th Edition (1996), 6381, p.1079
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