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
CAS Number	3270-98-2
3D model (JSmol)	Interactive image
ChemSpider	28533124
PubChem CID	5280366
InChI 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
SMILES O=C/C=C\C=C(\O)C(=O)O
Properties
Chemical formula	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]}

catechol

 

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

+ NADH

 

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

 

2-oxopent-4-enoic acid

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.