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.

catechol
 
O2
 
O2
 
 
2-hydroxymuconate semialdehyde

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

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

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

2-hydroxymuconate semialdehyde
 
H2O
HCO2H
H2O
HCO2H
 
2-oxopent-4-enoic acid
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