3D model (Jmol)
|Molar mass||142.11 g·mol−1|
|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)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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-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 (PET).
- Merck Index, 11th Edition, 6210
- trans,trans-Muconic acid at Sigma-Aldrich
- Merck Index, 12th Edition (1996), 6381, p.1079
- 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.
- 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 &. 104 (3): 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC . PMID 8919771.
- Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
- 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.