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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.

Additional recommended knowledge


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

  1. ^ Merck Index, 11th Edition, 6210.
  2. ^ trans,trans-Muconic acid at Sigma-Aldrich
  3. ^ 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.
  4. ^ 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.
  5. ^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Muconic_acid". A list of authors is available in Wikipedia.
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