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Muconic acid

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trans,trans-Muconic acid
Names
IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid
Other names (E,E)-Muconic acid
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.020.659 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • OC(\C=C/C=C\C(O)=O)=O
Properties
Chemical 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)
Boiling point 320 °C
Solubility in water 1 g/5 L at 15 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
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. Synthetically, trans,trans-muconic acid can be prepared from adipic acid.

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

See also

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. 104 (3). Brogan &#38: 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC 1469300. PMID 8919771. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  6. Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
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