Chemistry:2-Hydroxymuconate semialdehyde

From HandWiki
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
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).
Infobox references

2-Hydroxymuconate semialdehyde is formed from catechol by the enzyme catechol 2,3-dioxygenase during the degradation of benzoates.[1][2]

  1. REDIRECT Template:Chemical reaction

It is oxidised to (2E,4Z)-2-hydroxymuconic acid] by the enzyme 2-hydroxymuconate-6-semialdehyde dehydrogenase.[3]

  1. REDIRECT Template:Chemical reaction

It is also degraded into formate and 2-oxopent-4-enoic acid by 2-hydroxymuconate-semialdehyde hydrolase.[4]

  1. REDIRECT Template:Chemical reaction

References

  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. 
  2. Enzyme 1.13.11.2 at KEGG Pathway Database.
  3. "Uncovering the protocatechuate 2,3-cleavage pathway genes". Journal of Bacteriology 191 (21): 6758–68. November 2009. doi:10.1128/JB.00840-09. PMID 19717587. 
  4. "The meta cleavage of catechol by Azotobacter species 4-Oxalocrotonate pathway". European Journal of Biochemistry 20 (3): 400–13. 1971. doi:10.1111/j.1432-1033.1971.tb01406.x. PMID 4325686.