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{{distinguish|meconic acid}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 398801716
| Watchedfields = changed
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| Reference=<ref>''Merck Index'', 11th Edition, '''6210'''.</ref><ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/M90003 ''trans,trans''-Muconic acid] at [[Sigma-Aldrich]]</ref>
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| verifiedrevid =
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| Name=''trans,trans''-Muconic acid
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| Reference=<ref>''Merck Index'', 11th Edition, '''6210'''</ref><ref>[://www.sigmaaldrich.com///// Muconic acid] at [[Sigma-Aldrich]]</ref>
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| 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 = (,)-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
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| PubChem = 5356793
| UNII_Ref = {{fdacite|correct|FDA}}
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| SMILES = OC(\C=C/C=C\C(O)=O)=O
| UNII = 3KD92ZL2KH
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| PubChem = 5356793
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| 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>
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| Appearance = Crystalline prisms
| MolarMass = 142.11 g/mol
| Density = 1.366 g/mL
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| Appearance = Crystalline prisms
| Density =
|
| 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>
| = (cis,cisform, prisms from ethanol), 301°C (trans,trans-form, prisms from water), °C (cis,trans-form, needles from hot water)<ref>Merck Index 12th Edition (1996), 6381, p.1079</ref>
| BoilingPt = 320 °C
| =
| Solubility = 1 g/5 L at 15 °C
| Solubility = 1 g/L
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}}
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| Section3 = {{Chembox Hazards
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| MainHazards =
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| FlashPt =
| Autoignition =
}}
}}
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|Section3={{Chembox Hazards
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| MainHazards =
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| FlashPt =
| AutoignitionPt =
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}}
}}
}}

:''Not to be confused with [[meconic acid]], an unrelated dicarboxylic acid''
'''Muconic acid''' is a dicarboxylic acid. There are three [[isomer]]ic forms designated ''trans,trans''-muconic acid, ''cis,trans''-muconic acid, and ''cis,cis''-muconic acid which differ by the geometry around the [[double bond]]s.
'''Muconic acid''' is a dicarboxylic acid. There are three [[isomer]]ic forms designated ''trans,trans''-muconic acid, ''cis,trans''-muconic acid, and ''cis,cis''-muconic acid which differ by the geometry around the [[double bond]]s.


:{| class="toccolours" border="0" style="left"
:{| class="toccolours" border="0" style="left"
| align="center" | [[Image:muconic acid EE.png|150px]]
| align="center" | [[Image:muconic acid EE.png|150px]]
| align="center"| [[Image:muconic acid EZ.png|130px]]
| align="center"| [[Image:muconic acid EZ.png|130px]]
| align="center"|[[Image:muconic acid ZZ.png|130px]]
| align="center"|[[Image:muconic acid ZZ.png|130px]]
|-
|-
| align="center"|''trans,trans''
| align="center"|trans,trans
| align ="center"| [[Image:(Z,E)-Muconic-acid-3D-balls.png|130px|alt= Ball-and-stick model of the cis,trans-muconic acid molecule]]
⚫
| align="center"|''cis,trans''
| align ="center"|[[Image:(Z,Z)-Muconic-acid-3D-balls.png|130px|alt= Ball-and-stick model of the cis,cis-muconic acid molecule]]
⚫
| align="center"|''cis,cis''
|-
| align ="center"|''trans,trans''
⚫
| align="center"|''cis,trans''
⚫
| align="center"|''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.<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 [[adipic acid]].<ref>''Organic Syntheses'', Coll. Vol. 3, p.623 (1955); Vol. 26, p.57 (1946). [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0623 Online copy]</ref>
''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.<ref>{{cite journal |=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 |volume=35 |issue=2 |pages=268–9 |year=2007 |pmid=17366320 |doi=10.1080/01926230601156278}}</ref><ref>{{cite journal |=Weaver VM, Davoli CT, Heller PJ, |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 [[adipic acid]].<ref>Organic Syntheses. . . . ./orgsyn.= </ref>


''cis,cis''-Muconic acid is produced by some bacteria by the enzymatic degradation of various [[aromatic]] chemical compounds.
''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 66|nylon-6,6]], [[polyurethane]], and [[polyethylene terephthalate]].<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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[[Category:Dicarboxylic acids]]
[[Category:Dicarboxylic acids]]

[[fr:Acide muconique]]
[[it:Acido muconico]]
[[nl:Muconzuur]]
[[pt:Ácido mucônico]]
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