Muconic acid

trans,trans-Muconic acid[1][2]
IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid
Other names (E,E)-Muconic acid
Identifiers
CAS number	3588-17-8 Y
PubChem	5356793
Jmol-3D images	Image 1
SMILES OC(\C=C/C=C\C(O)=O)=O
Properties
Molecular formula	C6H6O4
Molar mass	142.11 g/mol
Appearance	Crystalline prisms
Melting point	194–195 °C (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	320 °C
Solubility in water	1 g/5 L at 15 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Not to be confused with meconic acid, an unrelated dicarboxylic 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.

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.

See also

• Dicarboxylic acid
• 2-Aminomuconic acid

Notes

1. ^ Merck Index, 11th Edition, 6210.
2. ^ trans,trans-Muconic acid at Sigma-Aldrich
3. ^ Merck Index 12th Edition (1996), 6381, p.1079.
4. ^ Wiwanitkit V, Soogarun S, Suwansaksri J (2007). "A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure". Toxicologic pathology 35 (2): 268–9. doi:10.1080/01926230601156278. PMID 17366320. 
5. ^ Weaver VM, Davoli CT, Heller PJ, et al. (1996). "Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels". Environ. Health Perspect. (Brogan &#38) 104 (3): 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC 1469300. PMID 8919771. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1469300. 
6. ^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy