Maleylacetic acid

Maleylacetic acid

Chemical structure of maleylacetic acid
Names
IUPAC name 4-Oxohex-2-enedioic acid
Other names 2-Maleylacetic acid Maleoylacetic acid
Identifiers
CAS Number	24740-88-3 (2Z)
3D model (JSmol)	Interactive image
Beilstein Reference	8404489
ChEBI	CHEBI:19672
ChemSpider	4575314 (2E) 4444140 (2Z) 406 ()
KEGG	C02222
MeSH	Maleoylacetic+acid
PubChem CID	5462172  (2E) 5280500  (2Z) 419  ()
CompTox Dashboard (EPA)	DTXSID001029401
InChI InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11) Key: SOXXPQLIZIPMIZ-UHFFFAOYSA-N
SMILES OC(=O)CC(=O)C=CC(O)=O
Properties
Chemical formula	C6H6O5
Molar mass	158.10 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Maleylacetic acid is a chemical compound produced in the biodegradation of catechin by Bradyrhizobium japonicum . ^[1]

In Moraxella species, the compound is a product of the metabolism of hydroquinone, with the final step being from oxidation of 4-hydroxymuconic semialdehyde: ^[2]

4-hydroxymuconic semialdehyde

+ NAD⁺

 

 

H₂O

H⁺

H₂O

H⁺

 

maleylacetic acid

+ NADH

 

The compound is reduced to 3-oxoadipic acid by the enzyme maleylacetate reductase in Trichosporon cutaneum : ^{[3] [4]}

maleylacetic acid

+ NADH

 

 

H⁺

 

H⁺

 

 

3-oxoadipic acid

+ NAD⁺

 

References

1. Hopper, Waheeta; Mahadevan, A. (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074.
2. Spain, Jim C.; Gibson, David T. (1991). "Pathway for Biodegradation of p -Nitrophenol in a Moraxella sp". Applied and Environmental Microbiology. 57 (3): 812–819. doi:10.1128/aem.57.3.812-819.1991. PMC   182799 . PMID   16348446.
3. Gaal, A. B.; Neujahr, H. Y. (1980). "Maleylacetate reductase from Trichosporon cutaneum". Biochemical Journal. 185 (3): 783–786. doi:10.1042/bj1850783. PMC   1161460 . PMID   7387635.
4. Gaal, Andras; Neujahr, Halina Y. (1981). "Induction of phenol-metabolizing enzymes in Trichosporon cutaneum". Archives of Microbiology. 130: 54–58. doi:10.1007/BF00527072. PMID   7305599.