Muconic acid

Not to 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	cis,trans	cis,cis

Muconic acid^[1][2]

Names
IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid
Other names (E,E)-Muconic acid
Identifiers
CAS Number	3588-17-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27036 N
ChemSpider	4512358 N
ECHA InfoCard	100.020.659
EC Number	222-724-8
PubChem CID	5356793
UNII	3KD92ZL2KH Y
CompTox Dashboard (EPA)	DTXSID9052848
InChI 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
SMILES OC(\C=C/C=C\C(O)=O)=O
Properties
Chemical formula	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)
Solubility in water	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). N verify (what is YN ?) Infobox references

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

• Dicarboxylic acid
• 2-Aminomuconic acid