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3-Carboxy-cis,cis-muconic acid

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3-Carboxy-cis,cis-muconic acid
Skeletal formula of 3-carboxy-cis,cis-muconic acid
Skeletal formula of 3-carboxy-cis,cis-muconic acid
Names
Preferred IUPAC name (1E,3Z)-Buta-1,3-diene-1,2,4-tricarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h1-3H,(H,8,9)(H,10,11)(H,12,13)/b2-1-,4-3+Key: KJOVGYUGXHIVAY-BXTBVDPRSA-N
  • InChI=1/C7H6O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h1-3H,(H,8,9)(H,10,11)(H,12,13)/b2-1-,4-3+Key: KJOVGYUGXHIVAY-BXTBVDPRBN
SMILES
  • OC(=O)\C=C/C(=C\C(O)=O)/C(O)=O
Properties
Chemical formula C7H6O6
Molar mass 186.119 g·mol
Density 1.25 g cm
Dipole moment 0.40 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

3-Carboxy-cis,cis-muconic acid is a metabolite of the catechin degradation by Bradyrhizobium japonicum.

The enzyme 3-carboxy-cis,cis-muconate cycloisomerase uses 2-carboxy-2,5-dihydro-5-oxofuran-2-acetate to produce 3-carboxy-cis,cis-muconate.

The enzyme carboxy-cis,cis-muconate cyclase uses 3-carboxy-2,5-dihydro-5-oxofuran-2-acetate to produce 3-carboxy-cis,cis-muconate.

The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate.

References

  1. "(1E,3Z)-buta-1,3-diene-1,2,4-tricarboxylic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 13 October 2011.
  2. Waheeta Hopper and A. Mahadevan (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074. S2CID 41221044.


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