Muconic acid

From Wikipedia, the free encyclopedia
  (Redirected from (E,E)-muconic acid)
Jump to: navigation, search
trans,trans-Muconic acid[1][2]
Muconic acid EE.png
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
Properties
C6H6O4
Molar mass 142.11 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
Main hazards Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox 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.

 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.[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 (PET).[7]

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. PMID 17366320. doi:10.1080/01926230601156278. 
  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. JSTOR 3432891. PMC 1469300Freely accessible. PMID 8919771. doi:10.2307/3432891. 
  6. ^ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
  7. ^ Curran KA, Leavitt JM, Karim AS, Alper HS (2013). "Metabolic engineering of muconic acid production in Saccharomyces cerevisiae.". Metab. Eng. 15: 55–66. PMID 23164574. doi:10.1016/j.ymben.2012.10.003.