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Revision as of 21:01, 30 June 2011 editLuckas-bot (talk | contribs)929,662 editsm r2.7.1) (robot Adding: fr:Acide muconique← Previous edit Latest revision as of 19:36, 25 September 2023 edit undoTrappist the monk (talk | contribs)Administrators479,773 editsm →top: cite repair;Tag: AWB 
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{{distinguish|meconic acid}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 398801716
| Watchedfields = changed
⚫ | Reference=<ref>''Merck Index'', 11th Edition, '''6210'''.</ref><ref> at ]</ref>
⚫ | verifiedrevid = 437115148
⚫ | Name=''trans,trans''-Muconic acid
⚫ | Reference =<ref>''Merck Index'', 11th Edition, '''6210'''</ref><ref> at ]</ref>
⚫ | Name =Muconic acid
| ImageFile1 = muconic acid EE.png | ImageFile1 = muconic acid EE.png
| ImageSize1 = 200px | ImageSize1 =
| IUPACName = (2E,4E)-Hexa-2,4-dienedioic acid | IUPACName = (2''E'',4''E'')-Hexa-2,4-dienedioic acid
| OtherNames = (E,E)-Muconic acid | OtherNames = (''E'',''E'')-Muconic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 3588-17-8 | CASNo = 3588-17-8
⚫ | PubChem = 5356793
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = OC(\C=C/C=C\C(O)=O)=O
| UNII = 3KD92ZL2KH
⚫ | PubChem = 5356793
⚫ | SMILES = OC(\C=C/C=C\C(O)=O)=O
| EINECS = 222-724-8
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4512358
| InChI = 1/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+
| InChIKey = TXXHDPDFNKHHGW-ZPUQHVIOBF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = TXXHDPDFNKHHGW-ZPUQHVIOSA-N
| RTECS =
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 27036
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=6 | O=4
| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>4</sub>
⚫ | Appearance = Crystalline prisms
| MolarMass = 142.11 g/mol
| Density = 1.366 g/mL
⚫ | Appearance = Crystalline prisms
| Density = | MeltingPtC = 194 to 195
| 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_notes = (''cis'',''cis''-form, prisms from ethanol), 301&nbsp;°C (''trans'',''trans''-form, prisms from water), 190–191&nbsp;°C (''cis'',''trans''-form, needles from hot water)<ref>'']'', 12th Edition (1996), 6381, p.1079</ref>
| BoilingPt = 320 °C | BoilingPtC = 345
| Solubility = 1 g/5 L at 15 °C | Solubility = 1 g/L
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards = Irritant
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}

:''Not to be confused with ], an unrelated dicarboxylic acid''
'''Muconic acid''' is a dicarboxylic acid. There are three ]ic forms designated ''trans,trans''-muconic acid, ''cis,trans''-muconic acid, and ''cis,cis''-muconic acid which differ by the geometry around the ]s. '''Muconic acid''' is a dicarboxylic acid. There are three ]ic forms designated ''trans,trans''-muconic acid, ''cis,trans''-muconic acid, and ''cis,cis''-muconic acid which differ by the geometry around the ]s. Its name is derived from ].


:{| class="toccolours" border="0" style="left" :{| class="toccolours" border="0" style="left"
| align="center" | ] | align ="center" | ]
| align="center"| ] | align ="center"| ]
| align="center"|] | align ="center"|]
|- |-
| align="center"|''trans,trans'' | align ="center" | ]
| align ="center"| ]
⚫ | align="center"|''cis,trans''
| align ="center"|]
⚫ | align="center"|''cis,cis''
|-
| align ="center"|''trans,trans''
⚫ | align ="center"|''cis,trans''
⚫ | align ="center"|''cis,cis''
|- |-
|} |}


''trans,trans''-Muconic acid is a ] of benzene in humans. The determination of its concentration in urine is therefore used as a ] of occupational or environmental exposure to benzene.<ref>{{cite journal |author=Wiwanitkit V, Soogarun S, Suwansaksri J |title=A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure |journal=Toxicologic pathology |volume=35 |issue=2 |pages=268–9 |year=2007 |pmid=17366320 |doi=10.1080/01926230601156278}}</ref><ref>{{cite journal |author=Weaver VM, Davoli CT, Heller PJ, ''et al.'' |title=Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels |journal=Environ. Health Perspect. |volume=104 |issue=3 |pages=318–23 |year=1996 |pmid=8919771 |doi=10.2307/3432891 |pmc=1469300 |jstor=3432891 |publisher=Brogan &#38}}</ref> Synthetically, ''trans,trans''-muconic acid can be prepared from ].<ref>''Organic Syntheses'', Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). </ref> ''trans,trans''-Muconic acid is a ] of benzene in humans. The determination of its concentration in urine is therefore used as a ] of occupational or environmental exposure to benzene.<ref>{{cite journal |vauthors=Wiwanitkit V, Soogarun S, Suwansaksri J |title=A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure |journal=Toxicologic Pathology |volume=35 |issue=2 |pages=268–9 |year=2007 |pmid=17366320 |doi=10.1080/01926230601156278|s2cid=6392962 }}</ref><ref>{{cite journal |vauthors=Weaver VM, Davoli CT, Heller PJ, etal |title=Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels |journal=Environ. Health Perspect. |volume=104 |issue=3 |pages=318–23 |year=1996 |pmid=8919771 |doi=10.2307/3432891 |pmc=1469300 |jstor=3432891 |publisher=Brogan &#38}}</ref> Synthetically, ''trans,trans''-muconic acid can be prepared from ].<ref>{{cite journal|journal=Organic Syntheses|volume=26|year=1946|author=P. C. Guha |author2=D. K. Sankaran |title=Muconic Acid|pages=57–60 |doi=10.15227/orgsyn.026.0057|pmid=20280761 }}</ref>


''cis,cis''-Muconic acid is produced by some bacteria by the enzymatic degradation of various ] chemical compounds. ''cis,cis''-Muconic acid is produced by some bacteria by the enzymatic degradation of various ] 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 ] including ], ], and ].<ref>{{cite journal|vauthors=Curran KA, Leavitt JM, Karim AS, Alper HS|title=Metabolic engineering of muconic acid production in Saccharomyces cerevisiae.|journal=Metab. Eng.|pmid=23164574|doi=10.1016/j.ymben.2012.10.003|volume=15|year=2013|pages=55–66}}</ref>


==See also== ==See also==
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