Muconic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
trans,trans-Muconic acid[1][2]
Muconic acid EE.png
Identifiers
CAS number 3588-17-8 YesY
PubChem 5356793
ChemSpider 4512358
EC number 222-724-8
ChEBI CHEBI:27036
Jmol-3D images Image 1
Properties
Molecular formula C6H6O4
Molar mass 142.11 g/mol
Appearance Crystalline prisms
Density 1.366 g/mL
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 345 °C
Solubility in water 1 g/5 L at 15 °C
Hazards
Main hazards Irritant
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

Muconic acid EE.png Muconic acid EZ.png Muconic acid ZZ.png
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[edit]

Notes[edit]

  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. 
  6. ^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy