Muconic acid

Muconic acid^[1]^[2]
Names
	IUPAC name (2E,4E)-Hexa-2,4-dienedioic acid
	Other names (E,E)-Muconic acid
Identifiers
CAS Number	3588-17-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27036 ;
ChemSpider	4512358 ;
ECHA InfoCard	100.020.659
EC Number	222-724-8;
PubChem CID	5356793;
UNII	3KD92ZL2KH ;
CompTox Dashboard (EPA)	DTXSID9052848 ;
	InChI InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ Key: TXXHDPDFNKHHGW-ZPUQHVIOSA-N ; 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+ Key: TXXHDPDFNKHHGW-ZPUQHVIOBF;
	SMILES OC(\C=C/C=C\C(O)=O)=O;
Properties
Chemical formula	C6H6O4
Molar mass	142.110 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)
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). 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. 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]

Notes

^ 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 &#38: 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.

[1] Merck Index, 11th Edition, 6210

[2] Muconic acid at Sigma-Aldrich

[3] Merck Index, 12th Edition (1996), 6381, p.1079

[4] 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.

[5] 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 &#38: 318–23. doi:10.2307/3432891. JSTOR 3432891. PMC 1469300. PMID 8919771.

[6] P. C. Guha; D. K. Sankaran (1946). "Muconic Acid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761.

[7] 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.

Muconic acid

See also

Notes