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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
PubChem	5356793
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	290 °C
Boiling point	320 °C
Solubility in water	1 g/5 L at 15 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.

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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.^[3]^[4] Synthetically, trans,trans-muconic acid can be prepared from adipic acid.^[5]

cis,cis-Muconic acid is produced by some bacteria by the enzymatic degradation of various aromatic chemical compounds.

References

^ Merck Index, 11th Edition, 6210.
^ trans,trans-Muconic acid at Sigma-Aldrich
^ 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.
^ 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. 104 (3): 318–23. PMID 8919771.
^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy