3-Carboxy-cis,cis-muconic acid

3-Carboxy-*cis*,*cis*-muconic acid
Names
	Preferred IUPAC name (1E,3Z)-Buta-1,3-diene-1,2,4-tricarboxylic acid
Identifiers
CAS Number	1116-26-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15749 ;
ChemSpider	4444085 ;
KEGG	C01163 ;
PubChem CID	5280404;
CompTox Dashboard (EPA)	DTXSID60415055 ;
	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−1
Density	1.25 g cm−3
Dipole moment	0.40 D
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Carboxy-cis,cis-muconic acid is a metabolite of the catechin degradation by Bradyrhizobium japonicum.^[2]

Biosynthesis

The enzyme protocatechuate 3,4-dioxygenase found in Pseudomonas aeruginosa uses protocatechuic acid and oxygen to produce 3-carboxy-cis,cis-muconate.^[3]

O₂

3-carboxy-cis,cis-muconic acid

The enzyme 3-carboxy-cis,cis-muconate cycloisomerase found in Pseudomonas putida converts 3-carboxy-cis,cis-muconate to 2-(carboxymethyl)-5-oxo-2,5-dihydro-2-furoic acid as part of a sequence which eventually gives β-ketoadipic acid.^[4]^[5]

2-(carboxymethyl)-5-oxo-2,5-dihydro-2-furoic acid

The enzyme carboxy-cis,cis-muconate cyclase gives the isomeric 2-(carboxymethyl)-5-oxo-2,5-dihydro-3-furoic acid as its product.^[6]

2-(carboxymethyl)-5-oxo-2,5-dihydro-3-furoic acid

^ "(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.
^ Waheeta Hopper and A. Mahadevan (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074. S2CID 41221044.
^ Fujisawa, H.; Hayaishi, O. (1968). "Protocatechuate 3,4-Dioxygenase". Journal of Biological Chemistry. 243 (10): 2673–2681. doi:10.1016/S0021-9258(18)93425-3.
^ Ornston LN (August 1966). "The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. II. Enzymes of the protocatechuate pathway". The Journal of Biological Chemistry. 241 (16): 3787–94. doi:10.1016/S0021-9258(18)99840-6. PMID 5916392.
^ Ornston LN (1970). "Conversion of catechol and protocatechuate to β-ketoadipate (Pseudomonas putida)". Conversion of catechol and protocatechuate to beta-ketoadipate (Pseudomonas putida). Methods Enzymol. Vol. 17A. pp. 529–549. doi:10.1016/0076-6879(71)17237-0. ISBN 978-0-12-181874-6.
^ Gross SR, Gafford RD, Tatum EL (1956). "The metabolism of protocatechuic acid by Neurospora". J. Biol. Chem. 219 (2): 781–96. doi:10.1016/S0021-9258(18)65737-0. PMID 13319299.