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2-Hydroxymuconate semialdehyde

From Wikipedia, the free encyclopedia
2-Hydroxymuconate semialdehyde
Names
Preferred IUPAC name
(2Z,4E)-2-Hydroxy-6-oxohexa-2,4-dienoic acid
Other names
hydroxymuconic semialdehyde; 2-hydroxymuconate semialdehyde; 2-hydroxymuconate-6-semialdehyde
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H6O4/c7-4-2-1-3-5(8)6(9)10/h1-4,8H,(H,9,10)/b2-1+,5-3-
    Key: KGLCZTRXNNGESL-WFTYEQLWSA-N
  • C(=C/C=O)\C=C(\C(=O)O)/O
Properties
C6H6O4
Molar mass 142.110 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Hydroxymuconate semialdehyde is formed from catechol by the enzyme catechol 2,3-dioxygenase during the degradation of benzoates.[1] It is hydrolysed into formate and 2-oxopent-4-enoate by 2-hydroxymuconate-semialdehyde hydrolase.

References

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  1. ^ Sala-Trepat JM, Evans WC (1971). "The meta cleavage of catechol by Azotobacter species 4-Oxalocrotonate pathway". Eur. J. Biochem. 20 (3): 400–13. doi:10.1111/j.1432-1033.1971.tb01406.x. PMID 4325686.