Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110036
Identification
Name: cis,cis-muconate
Description:A muconate that is the conjugate base of (2Z,4Z)-5-carboxypenta-2,4-dienoate.
Structure
Thumb
Synonyms:
  • cis,cis-hexadienedioate
  • (2Z,4Z)-hexa-2,4-dienedioate
Chemical Formula: C6H4O4
Average Molecular Weight: 140.1
Monoisotopic Molecular Weight: 142.026608681
InChI Key: TXXHDPDFNKHHGW-CCAGOZQPSA-L
InChI: InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/p-2/b3-1-,4-2-
CAS number: 1119-72-8
IUPAC Name:(2Z,4Z)-hexa-2,4-dienedioate
Traditional IUPAC Name: muconic acid
SMILES:[CH]([CH]=CC([O-])=O)=[CH]C([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Medium-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.48 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.93 m3·mol-1ChemAxon
Polarizability12.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-9bfca1b46934aca91417View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9100000000-f73acaf474e29ae6ad02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-9100000000-f2b4bdcda5ec550eb792View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-2900000000-1ba3b45cf195a5a99f0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-dfbcd30eacb1562a4b6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-55d282ca59f262ec6571View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-6d6fa71ac1d98156ceb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-b0b000b29f1354ee4c06View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Jaff? 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)
  • 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).
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS1119-72-8
ChEBI32379
ChemSpider5641039
HMDBHMDB06331
KEGGC02480
PubChem7310978