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)
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 [77 °F], 100 kPa).
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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.
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.[7]
^Merck Index, 11th Edition, 6210
^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. S2CID 6392962.
^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 &: 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC 1469300. PMID 8919771.
^P. C. Guha; D. K. Sankaran (1946). "Muconic Acid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761.
^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.
Muconicacid is a dicarboxylic acid. There are three isomeric forms designated trans,trans-muconicacid, cis,trans-muconicacid, and cis,cis-muconic acid...
derives from 18:2 or 18:3 fatty acid hydroperoxides after conversion into oxo- fatty acids. trans,trans-Muconicacid is a metabolite of benzene in humans...
enzymatically converted to a series of oxidation products including muconicacid, phenylmercapturic acid, phenol, catechol, hydroquinone and 1,2,4-trihydroxybenzene...
nylon 6,6. Adipamide Adiponitrile P. C. Guha; D. K. Sankaran (1946). "MuconicAcid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761...
blood, and urine, and metabolites such as phenol, t,t-muconicacid (t,tMA) and S-phenylmercapturic acid (sPMA) can be measured in urine. In addition to monitoring...
4-dioxygenase and hydroxyquinol 1,2-dioxygenase to form β-carboxy-cis,cis-muconicacid and maleyl acetate. Among fungi, degradation of catechin can be achieved...
186.01643790 u) may refer to: 3-Carboxy-cis,cis-muconicacid 3-Fumarylpyruvic acid 3-Maleylpyruvic acid This set index page lists chemical structure articles...
carried out by catechol 1,2-dioxygenase is the formation of cis,cis-muconicacid from catechol, shown below. Bioinorganic chemistry Oxygenase Stephen...
the veratryl group was then ring-opened with ozone in aqueous acetic acid to muconic ester 11 (made possible by the two electron-donating methoxide groups)...