Muconic 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. Its name is derived from mucic acid.

Skeletal formula of trans,trans-muconic acid Skeletal formula of cis,trans-muconic acid Skeletal formula of cis,cis-muconic acid
Ball-and-stick model of the trans,trans-muconic acid molecule Ball-and-stick model of the cis,trans-muconic acid molecule Ball-and-stick model of the cis,cis-muconic acid molecule
trans,trans cis,trans cis,cis
Not to be confused with meconic acid.
Muconic acid[1][2]
Names
IUPAC name
(2E,4E)-Hexa-2,4-dienedioic acid
Other names
(E,E)-Muconic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.659
EC Number
  • 222-724-8
UNII
  • InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ ☒N
    Key: TXXHDPDFNKHHGW-ZPUQHVIOSA-N ☒N
  • InChI=1/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+
    Key: TXXHDPDFNKHHGW-ZPUQHVIOBF
  • OC(\C=C/C=C\C(O)=O)=O
Properties
C6H6O4
Molar mass 142.110 g·mol−1
Appearance Crystalline prisms
Density 1.366 g/mL
Melting point 194 to 195 °C (381 to 383 °F; 467 to 468 K) (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 (653 °F; 618 K)
1 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

The bioproduction of muconic acid is of interest because of its potential use as a platform chemical for the production of several valuable consumer bioplastics including nylon-6,6, polyurethane, and polyethylene terephthalate.[7]

See also

Notes
  1. Merck Index, 11th Edition, 6210
  2. 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. S2CID 6392962.
  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. P. C. Guha; D. K. Sankaran (1946). "Muconic Acid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761.
  7. Curran KA, Leavitt JM, Karim AS, Alper HS (2013). "Metabolic engineering of muconic acid production in Saccharomyces cerevisiae". Metab. Eng. 15: 55–66. doi:10.1016/j.ymben.2012.10.003. PMID 23164574.
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