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Record Information
Version1.0
Created at2007-05-23 00:53:22 UTC
Updated at2021-06-30 02:06:15 UTC
NP-MRD IDNP0001219
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis,cis-Muconic acid
DescriptionCis-cis-Muconic acid is a presumptive metabolite of benzene. Muconic acid was first isolated from the urine of rabbits and dogs in 1909 (M. Jaffe, Z Physiol Chem 62:58-67). It was originally thought that if muconic acid was formed by the opening of the benzene ring in vivo then the cis-cis isomer should be the initial (and primary) product. However subsequent studies conducted in the 1950s proved that trans-trans-muconic acid is a true metabolite of benzene in mammals (Parke DV, Williams RT. Biochem J 51:339-348 (1952)). Furthermore, dosing rabbits with phenol or catechol also resulted in the urinary excretion of trans-trans-muconic acid. The oxidative ring opening of benzene first gives rise to cis-cis-muconaldehyde, which then isomerizes to cis-trans- and trans-trans-muconaldehyde; the latter is oxidized in vivo to trans-trans-muconic acid. Isomerization of the trans-trans form may take place in vivo to yield small amounts if the cis-cis and cis-trans form of muconic acid. Cis-cis-Muconic acid may also be generated from microbial fermentation of benzoic acid. Certain strains of arthobacter are particularly efficient at this process. Cis-cis-Muconic acid can also be found in Pseudomonas and Escherichia coli (https://Link.Springer.Com/article/10.1007/BF00250491) (PMID:26360870 ).
Structure
Thumb
Synonyms
ValueSource
(2Z,4Z)-HEXA-2,4-dienedioIC ACIDChEBI
(Z,Z)-2,4-Hexadienedioic acidChEBI
cis,cis-2,4-Hexadienedioic acidChEBI
cis,cis-HexadienedioateKegg
(2Z,4Z)-HEXA-2,4-dienedioateGenerator
(Z,Z)-2,4-HexadienedioateGenerator
cis,cis-2,4-HexadienedioateGenerator
cis,cis-Hexadienedioic acidGenerator
cis,cis-MuconateGenerator
trans-trans-MuconateHMDB
2,4-HexadienedioateHMDB
2,4-Hexadienedioic acidHMDB
Muconic acidHMDB
Muconic acid, (e,e)-isomerHMDB
trans-beta-Hydromuconic acidHMDB
trans,trans-Muconic acidHMDB
Chemical FormulaC6H6O4
Average Mass142.1094 Da
Monoisotopic Mass142.02661 Da
IUPAC Name(2Z,4Z)-hexa-2,4-dienedioic acid
Traditional Namemuconic acid
CAS Registry Number1119-72-8
SMILES
OC(=O)\C=C/C=C\C(O)=O
InChI Identifier
InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
InChI KeyTXXHDPDFNKHHGW-CCAGOZQPSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Plakortis simplexLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Pseudomonas putidaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.48 g/LALOGPS
logP0.67ALOGPS
logP0.49ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.93 m³·mol⁻¹ChemAxon
Polarizability12.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006331
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023893
KNApSAcK IDC00007490
Chemspider ID4444151
KEGG Compound IDC02480
BioCyc IDNot Available
BiGG ID36677
Wikipedia LinkMuconic acid
METLIN IDNot Available
PubChem Compound5280518
PDB IDNot Available
ChEBI ID16508
Good Scents IDNot Available
References
General References
  1. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]
  2. Vyas TK, Murthy SR: Chlorobenzene degradation by Bacillus sp. TAS6CB: a potential candidate to remediate chlorinated hydrocarbon contaminated sites. J Basic Microbiol. 2015 Mar;55(3):382-8. doi: 10.1002/jobm.201200758. Epub 2013 May 29. [PubMed:23720149 ]
  3. Xie NZ, Wang QY, Zhu QX, Qin Y, Tao F, Huang RB, Xu P: Optimization of medium composition for cis,cis-muconic acid production by a Pseudomonas sp. mutant using statistical methods. Prep Biochem Biotechnol. 2014;44(4):342-54. doi: 10.1080/10826068.2013.829497. [PubMed:24320235 ]
  4. Mori Y, Noda S, Shirai T, Kondo A: Direct 1,3-butadiene biosynthesis in Escherichia coli via a tailored ferulic acid decarboxylase mutant. Nat Commun. 2021 Apr 13;12(1):2195. doi: 10.1038/s41467-021-22504-6. [PubMed:33850144 ]
  5. Jensen ED, Ambri F, Bendtsen MB, Javanpour AA, Liu CC, Jensen MK, Keasling JD: Integrating continuous hypermutation with high-throughput screening for optimization of cis,cis-muconic acid production in yeast. Microb Biotechnol. 2021 Mar 1. doi: 10.1111/1751-7915.13774. [PubMed:33645919 ]
  6. Presley GN, Werner AZ, Katahira R, Garcia DC, Haugen SJ, Ramirez KJ, Giannone RJ, Beckham GT, Michener JK: Pathway discovery and engineering for cleavage of a beta-1 lignin-derived biaryl compound. Metab Eng. 2021 May;65:1-10. doi: 10.1016/j.ymben.2021.02.003. Epub 2021 Feb 23. [PubMed:33636323 ]
  7. Wang G, Moller-Hansen I, Babaei M, D'Ambrosio V, Christensen HB, Darbani B, Jensen MK, Borodina I: Transportome-wide engineering of Saccharomyces cerevisiae. Metab Eng. 2021 Mar;64:52-63. doi: 10.1016/j.ymben.2021.01.007. Epub 2021 Jan 16. [PubMed:33465478 ]
  8. Lubbers RJM, Dilokpimol A, Visser J, Hilden KS, Makela MR, de Vries RP: Discovery and Functional Analysis of a Salicylic Acid Hydroxylase from Aspergillus niger. Appl Environ Microbiol. 2021 Feb 26;87(6). pii: AEM.02701-20. doi: 10.1128/AEM.02701-20. Print 2021 Feb 26. [PubMed:33397706 ]
  9. Reifenrath M, Oreb M, Boles E, Tripp J: Artificial ER-Derived Vesicles as Synthetic Organelles for in Vivo Compartmentalization of Biochemical Pathways. ACS Synth Biol. 2020 Nov 20;9(11):2909-2916. doi: 10.1021/acssynbio.0c00241. Epub 2020 Oct 19. [PubMed:33074655 ]
  10. (). Jaffé M. Cleavage of the benzene ring in the organism. 1. The excretion of muconic acid in the urine after ingestion of benzene. Z Physiol Chem 62:58-67 (1909). .
  11. (). Parke DV, Williams RT. Studies in detoxication 44. The metabolism of benzene. The muconic acid excreted by rabbits receiving benzene. Determination of the isomeric muconic acids. Biochem J 51:339-348 (1952).. .