Muconic acid
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Names | |
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IUPAC name
(2E,4E)-Hexa-2,4-dienedioic acid
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Other names
(E,E)-Muconic acid
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Identifiers | |
3588-17-8 | |
ChEBI | CHEBI:27036 |
ChemSpider | 4512358 |
EC Number | 222-724-8 |
Jmol 3D model | Interactive image |
PubChem | 5356793 |
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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 | |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
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.
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
Notes
- ↑ Merck Index, 11th Edition, 6210
- ↑ trans,trans-Muconic acid at Sigma-Aldrich
- ↑ Merck Index, 12th Edition (1996), 6381, p.1079
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- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy
- ↑ Lua error in package.lua at line 80: module 'strict' not found.