2-Hydroxymuconate semialdehyde

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+ Y
    Key: KGLCZTRXNNGESL-REDYYMJGSA-N Y
  • O=C/C=C\C=C(\O)C(=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).
Infobox references

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

 
O2
 
O2
 
 
2-hydroxymuconate semialdehyde

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

2-hydroxymuconate semialdehyde
+ NAD+
 
 
H2O
H+
H2O
H+
 
(2E,4Z)-2-hydroxymuconic acid
 

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

2-hydroxymuconate semialdehyde
 
H2O
HCO2H
H2O
HCO2H
 

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. ^ Kasai D, Fujinami T, Abe T, Mase K, Katayama Y, Fukuda M, Masai E (November 2009). "Uncovering the protocatechuate 2,3-cleavage pathway genes". Journal of Bacteriology. 191 (21): 6758–68. doi:10.1128/JB.00840-09. PMC 2795304. PMID 19717587.
  4. ^ Sala-Trepat JM, Evans WC (1971). "The meta cleavage of catechol by Azotobacter species 4-Oxalocrotonate pathway". European Journal of Biochemistry. 20 (3): 400–13. doi:10.1111/j.1432-1033.1971.tb01406.x. PMID 4325686.