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| | MolarMass = 142.11 g/mol | | MolarMass = 142.11 g/mol | ||
| | Appearance = Crystalline prisms | | Appearance = Crystalline prisms | ||
| | Density = | | Density = 1.366 g/mL | ||
| | MeltingPt = 194–195 °C (cis,cis form, prisms from ethanol), 301 °C (trans,trans-form, prisms from water), 190–191 °C (cis,trans-form, needles from hot water)<ref>Merck Index 12th Edition (1996), 6381, p.1079.</ref> | | MeltingPt = 194–195 °C (cis,cis form, prisms from ethanol), 301 °C (trans,trans-form, prisms from water), 190–191 °C (cis,trans-form, needles from hot water)<ref>Merck Index 12th Edition (1996), 6381, p.1079.</ref> | ||
| | BoilingPt = |
| BoilingPt = 345 °C | ||
| | Solubility = 1 g/5 L at 15 °C | | Solubility = 1 g/5 L at 15 °C | ||
| }} | }} | ||
| | Section3 = {{Chembox Hazards | | Section3 = {{Chembox Hazards | ||
| | MainHazards = | | MainHazards = Irritant | ||
| | FlashPt = | | FlashPt = | ||
| | Autoignition = | | Autoignition = | ||
Revision as of 02:19, 26 December 2012
 | |
| Names | |
|---|---|
| IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid | |
| Other names (E,E)-Muconic acid | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ECHA InfoCard | 100.020.659 
|
| PubChem CID | |
| CompTox Dashboard (EPA) | |
SMILES
| |
| Properties | |
| Chemical formula | C6H6O4 |
| Molar mass | 142.11 g/mol |
| Appearance | Crystalline prisms |
| Density | 1.366 g/mL |
| Melting point | 194–195 °C (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 |
| Solubility in water | 1 g/5 L at 15 °C |
| 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).
 Y verify (what is ?)
Infobox references
| |
- Not to be confused with meconic acid, an unrelated dicarboxylic acid
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 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.
See also
Notes
- 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - 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.
{{cite journal}}: Explicit use of et al. in:|author=(help)CS1 maint: multiple names: authors list (link) - Organic Syntheses, Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). Online copy