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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 00:53:22 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006331
Secondary Accession Numbers
  • HMDB06331
Metabolite 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 Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
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
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDCCMUAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. (). 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). .
  3. (). 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).. .