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Muconic acid

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Revision as of 19:36, 25 September 2023 by Trappist the monk (talk | contribs) (→top: cite repair;)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Not to be confused with meconic acid.
Muconic acid
Names
IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid
Other names (E,E)-Muconic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.659 Edit this at Wikidata
EC Number
  • 222-724-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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+Key: TXXHDPDFNKHHGW-ZPUQHVIOSA-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
SMILES
  • OC(\C=C/C=C\C(O)=O)=O
Properties
Chemical formula C6H6O4
Molar mass 142.110 g·mol
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)
Boiling point 345 °C (653 °F; 618 K)
Solubility in water 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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.

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.

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. 104 (3). Brogan &#38: 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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