Record Information
Version1.0
Creation date2011-09-21 00:22:38 UTC
Update date2015-07-21 06:57:27 UTC
Primary IDFDB022974
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-trans-Muconic acid
Descriptiontrans,trans-Muconic acid is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in humans exposed to levels as low as 1 ppm. However, muconic acid is known that may also be derived from sorbic acid and its salts. Dietary supplementation with 500 mg sorbic acid significantly increases the urinary trans,trans-Muconic acid excretion. Under study conditions 0.12% of the sorbic acid dose is excreted in urine as trans, trans muconic acid thereby indicating that a typical dietary intake of 6 - 30 mg/day of sorbic acid accounts for 10 -50% of the background of trans, trans muconic acid excretion in nonsmokers, and for 5 - 25% in smokers. (PMID 8021961, 1487326, 9137998, Int Arch Occup Environ Health. 1997;69(4):247-51.) [HMDB]
CAS Number3588-17-8
Structure
Thumb
Synonyms
SynonymSource
(2E,4E)-2,4-Hexadienedioic acidChEBI
(e,e)-2,4-Hexadienedioic acidChEBI
(e,e)-Muconic acidChEBI
trans,trans-1,3-Butadiene-1,4-dicarboxylic acidChEBI
trans,trans-2,4-Hexadienedioic acidChEBI
trans,trans-Buta-1,3-diene-1,4-dicarboxylic acidChEBI
(2E,4E)-2,4-HexadienedioateGenerator
(e,e)-2,4-HexadienedioateGenerator
(e,e)-MuconateGenerator
trans,trans-1,3-Butadiene-1,4-dicarboxylateGenerator
trans,trans-2,4-HexadienedioateGenerator
trans,trans-Buta-1,3-diene-1,4-dicarboxylateGenerator
trans-trans-MuconateGenerator
cis,cis-MuconateMeSH
Muconic acidMeSH
Muconic acid, (e,e)-isomerMeSH
trans-beta-Hydromuconic acidMeSH
1,3-Butadiene-1,4-dicarboxylateHMDB
1,3-Butadiene-1,4-dicarboxylic acidHMDB
Hexa-2,4-dienedioateHMDB
Hexa-2,4-dienedioic acidHMDB
trans,trans-Muconic acidHMDB
(E,E)-2,4-Hexadienedioatehmdb
(E,E)-2,4-Hexadienedioic acidhmdb
(E,E)-Muconatehmdb
(E,E)-Muconic acidhmdb
trans,trans-MuconateGenerator
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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-ba0597e9fe553580b776Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-9700000000-bb11fdbd4cb83319bdcfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-60049330475bcfa51fddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-d089e6c88da6929f4c62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5900000000-d4f0aa2255b01aabc0bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdp-9300000000-bc5a2d5e39f202b87d9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-9600000000-3e5c79b293ac84a6a831Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-b7fce2b042b06e3cb276Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9000000000-5b8045afa89b9f96b99dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-5b62b2b14bc9b75cd848Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9000000000-20df0bac53b1a654f39bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9000000000-e2a3f3d1e8945188e022Spectrum
NMRNot Available
ChemSpider ID4512358
ChEMBL IDCHEMBL1922185
KEGG Compound IDNot Available
Pubchem Compound ID5356793
Pubchem Substance IDNot Available
ChEBI ID27036
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02349
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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