Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002349
Secondary Accession Numbers
  • HMDB02349
Metabolite Identification
Common 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 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.). trans,trans-Muconic acid has been found to be a metabolite in Escherichia coli and Pseudomonas putida (PMID: 26360870 ).
Structure
Data?1582752244
Synonyms
ValueSource
(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
Chemical FormulaC6H6O4
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
IUPAC Name(2E,4E)-hexa-2,4-dienedioic acid
Traditional Nametrans, trans-muconic acid
CAS Registry Number3588-17-8
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-ZPUQHVIOSA-N
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point301 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.17131661259
DarkChem[M-H]-129.32431661259
DeepCCS[M+H]+125.89430932474
DeepCCS[M-H]-122.06530932474
DeepCCS[M-2H]-159.1430932474
DeepCCS[M+Na]+134.52430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O2776.0Standard polar33892256
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O1320.6Standard non polar33892256
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O1539.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-trans-Muconic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O1583.1Semi standard non polar33892256
trans-trans-Muconic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O[Si](C)(C)C1642.4Semi standard non polar33892256
trans-trans-Muconic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O1841.7Semi standard non polar33892256
trans-trans-Muconic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O[Si](C)(C)C(C)(C)C2116.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-MS (2 TMS)splash10-00di-3950000000-4833ed03fecc5d1070872014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized)splash10-00di-3950000000-4833ed03fecc5d1070872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-25984cbefee561769fe32017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9400000000-1d771b996d6b60d972022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-8930000000-43cca1649a383c1789572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Positive-QTOFsplash10-002f-1900000000-ba0597e9fe553580b7762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Positive-QTOFsplash10-004m-9700000000-bb11fdbd4cb83319bdcf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Positive-QTOFsplash10-0udi-9000000000-60049330475bcfa51fdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Negative-QTOFsplash10-0006-1900000000-d089e6c88da6929f4c622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Negative-QTOFsplash10-0006-5900000000-d4f0aa2255b01aabc0bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Negative-QTOFsplash10-0fdp-9300000000-bc5a2d5e39f202b87d9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Positive-QTOFsplash10-004j-9600000000-3e5c79b293ac84a6a8312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Positive-QTOFsplash10-004i-9200000000-b7fce2b042b06e3cb2762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Positive-QTOFsplash10-0udr-9000000000-5b8045afa89b9f96b99d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Negative-QTOFsplash10-0002-9200000000-5b62b2b14bc9b75cd8482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Negative-QTOFsplash10-0fb9-9000000000-20df0bac53b1a654f39b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Negative-QTOFsplash10-0fb9-9000000000-e2a3f3d1e8945188e0222021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.03 +/- 0.016 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.1 (0.05 - 0.3) umol/mmol creatinineAdult (>18 years old)BothSmoking details
UrineDetected and Quantified0.16 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Male
Benzene exposure
details
Associated Disorders and Diseases
Disease References
Benzene exposure
  1. Chanvaivit S, Navasumrit P, Hunsonti P, Autrup H, Ruchirawat M: Exposure assessment of benzene in Thai workers, DNA-repair capacity and influence of genetic polymorphisms. Mutat Res. 2007 Jan 10;626(1-2):79-87. Epub 2006 Nov 13. [PubMed:17095285 ]
Smoking
  1. Ruppert T, Scherer G, Tricker AR, Adlkofer F: trans,trans-muconic acid as a biomarker of non-occupational environmental exposure to benzene. Int Arch Occup Environ Health. 1997;69(4):247-51. [PubMed:9137998 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023893
KNApSAcK IDNot Available
Chemspider ID4512358
KEGG Compound IDNot Available
BioCyc ID25-DICHLORO-CISCIS-MUCONATE
BiGG IDNot Available
Wikipedia LinkMuconic_acid
METLIN ID6639
PubChem Compound5356793
PDB IDNot Available
ChEBI ID27036
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000390
Good Scents IDNot Available
References
Synthesis ReferenceErlenmeyer, H.; Schoenauer, W. A synthesis of trans-trans-muconic acid from fumaric acid. Helvetica Chimica Acta (1937), 20 1008-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Renner T, Baer-Koetzle M, Scherer G: Determination of sorbic acid in urine by gas chromatography-mass spectrometry. J Chromatogr A. 1999 Jun 25;847(1-2):127-33. [PubMed:10431356 ]
  2. Kim S, Vermeulen R, Waidyanatha S, Johnson BA, Lan Q, Rothman N, Smith MT, Zhang L, Li G, Shen M, Yin S, Rappaport SM: Using urinary biomarkers to elucidate dose-related patterns of human benzene metabolism. Carcinogenesis. 2006 Apr;27(4):772-81. Epub 2005 Dec 8. [PubMed:16339183 ]
  3. Wiwanitkit V, Suwansaksri J, Soogarun S: The urine trans, trans muconic acid biomarker and platelet count in a sample of subjects with benzene exposure. Clin Appl Thromb Hemost. 2004 Jan;10(1):73-6. [PubMed:14979410 ]
  4. Hecht SS: Human urinary carcinogen metabolites: biomarkers for investigating tobacco and cancer. Carcinogenesis. 2002 Jun;23(6):907-22. [PubMed:12082012 ]
  5. Ruppert T, Scherer G, Tricker AR, Adlkofer F: trans,trans-muconic acid as a biomarker of non-occupational environmental exposure to benzene. Int Arch Occup Environ Health. 1997;69(4):247-51. [PubMed:9137998 ]
  6. Bartczak A, Kline SA, Yu R, Weisel CP, Goldstein BD, Witz G, Bechtold WE: Evaluation of assays for the identification and quantitation of muconic acid, a benzene metabolite in human urine. J Toxicol Environ Health. 1994 Jul;42(3):245-58. [PubMed:8021961 ]
  7. Ducos P, Gaudin R, Bel J, Maire C, Francin JM, Robert A, Wild P: trans,trans-Muconic acid, a reliable biological indicator for the detection of individual benzene exposure down to the ppm level. Int Arch Occup Environ Health. 1992;64(5):309-13. [PubMed:1487326 ]
  8. 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 ]