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Muconic acid

Muconic acid[1][2]
Names
IUPAC name

(2E,4E)-Hexa-2,4-dienedioic acid

Other names

(E,E)-Muconic acid

Identifiers

3D model (JSmol)

ChEBI
ChemSpider
ECHA InfoCard 100.020.659 Edit this at Wikidata
EC Number
  • 222-724-8

PubChem CID

UNII

  • InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ ☒N

    Key: TXXHDPDFNKHHGW-ZPUQHVIOSA-N ☒N

  • InChI=1/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+

    Key: TXXHDPDFNKHHGW-ZPUQHVIOBF

  • OC(\C=C/C=C\C(O)=O)=O

Properties
C6H6O4
Molar mass 142.110 g·mol−1
Appearance Crystalline prisms
Density 1.366 g/mL
Melting point 194 to 195 °C (381 to 383 °F; 467 to 468 K) (cis,cis-form, prisms from ethanol), 301 °C (trans,trans-form, prisms from water), 190–191 °C (cis,trans-form, needles from hot water)[3]
Boiling point 345 °C (653 °F; 618 K)
1 g/L
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

Irritant

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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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.

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]