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.


 * {| class="toccolours" border="0" style="left"


 * align ="center" | [[Image:muconic acid EE.png|150px|alt= Skeletal formula of trans,trans-muconic acid]]
 * align ="center"| [[Image:muconic acid EZ.png|130px|alt= Skeletal formula of cis,trans-muconic acid]]
 * align ="center"|[[Image:muconic acid ZZ.png|130px|alt= Skeletal formula of cis,cis-muconic acid]]
 * align ="center" | [[Image:(E,E)-Muconic-acid-3D-balls.png|150px|alt= Ball-and-stick model of the trans,trans-muconic acid molecule]]
 * align ="center"| [[Image:(Z,E)-Muconic-acid-3D-balls.png|130px|alt= Ball-and-stick model of the cis,trans-muconic acid molecule]]
 * align ="center"|[[Image:(Z,Z)-Muconic-acid-3D-balls.png|130px|alt= Ball-and-stick model of the cis,cis-muconic acid molecule]]
 * align ="center"|trans,trans
 * align ="center"|cis,trans
 * align ="center"|cis,cis
 * }
 * align ="center"|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. 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.