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 ();
UNII	JAD9FA3JG6 ;
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⁺

Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left

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⁺

Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left

H⁺

3-oxoadipic acid

+ NAD⁺

References

↑ Hopper, Waheeta; Mahadevan, A. (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074.
↑ 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.
↑ 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.
↑ 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.

[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.

[1]

[2]

[3]

[4]

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References