Record Information
Version1.0
Creation date2011-09-21 00:36:30 UTC
Update date2015-10-09 22:32:57 UTC
Primary IDFDB023893
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 were formed by 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 1950's 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. [HMDB]
CAS Number1119-72-8
Structure
Thumb
Synonyms
SynonymSource
(2Z,4Z)-HEXA-2,4-dienedioateGenerator
(2Z,4Z)-HEXA-2,4-dienedioIC ACIDChEBI
(Z,Z)-2,4-hexadienedioatehmdb
(Z,Z)-2,4-hexadienedioic acidhmdb
2,4-Hexadienedioatehmdb
2,4-Hexadienedioic acidhmdb
cis,cis-2,4-Hexadienedioatehmdb
cis,cis-2,4-Hexadienedioic acidhmdb
Cis,cis-hexadienedioatehmdb
Cis,cis-hexadienedioic acidhmdb
Cis,cis-muconatehmdb
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
Polarizability12.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O4
IUPAC name(2E,4E)-hexa-2,4-dienedioic acid
InChI IdentifierInChI=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-ZPUQHVIOSA-N
Isomeric SMILESOC(=O)\C=C\C=C\C(O)=O
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
Classification
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MStrans-trans-Muconic acid, 2 TMS, GC-MS Spectrumsplash10-00di-3950000000-4833ed03fecc5d107087Spectrum
GC-MStrans-trans-Muconic acid, non-derivatized, GC-MS Spectrumsplash10-00di-3950000000-4833ed03fecc5d107087Spectrum
GC-MStrans-trans-Muconic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-25984cbefee561769fe3Spectrum
Predicted GC-MStrans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9400000000-1d771b996d6b60d97202Spectrum
Predicted GC-MStrans-trans-Muconic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-8930000000-43cca1649a383c178957Spectrum
Predicted GC-MStrans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-1900000000-ba0597e9fe553580b7762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-9700000000-bb11fdbd4cb83319bdcf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-60049330475bcfa51fdd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-d089e6c88da6929f4c622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5900000000-d4f0aa2255b01aabc0bf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdp-9300000000-bc5a2d5e39f202b87d9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-9600000000-3e5c79b293ac84a6a8312021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-b7fce2b042b06e3cb2762021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9000000000-5b8045afa89b9f96b99d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-5b62b2b14bc9b75cd8482021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9000000000-20df0bac53b1a654f39b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9000000000-e2a3f3d1e8945188e0222021-09-24View Spectrum
NMRNot Available
ChemSpider ID4444151
ChEMBL IDNot Available
KEGG Compound IDC02480
Pubchem Compound ID5280518
Pubchem Substance IDNot Available
ChEBI ID16508
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06331
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36677
KNApSAcK IDNot Available
HET IDCCU
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference