ChemFOnt: Showing chemical card for cis,cis-Muconic acid (CFc000002721)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:40 UTC

Chemfont ID

CFc000002721

Molecule Identification

Common Name

cis,cis-Muconic acid

Definition

cis-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E,4E)-2,4-Hexadienedioic acid	ChEBI
(e,e)-2,4-Hexadienedioic acid	ChEBI
(e,e)-Muconic acid	ChEBI
trans,trans-1,3-Butadiene-1,4-dicarboxylic acid	ChEBI
trans,trans-2,4-Hexadienedioic acid	ChEBI
trans,trans-Buta-1,3-diene-1,4-dicarboxylic acid	ChEBI
(2E,4E)-2,4-Hexadienedioate	Generator
(e,e)-2,4-Hexadienedioate	Generator
(e,e)-Muconate	Generator
trans,trans-1,3-Butadiene-1,4-dicarboxylate	Generator
trans,trans-2,4-Hexadienedioate	Generator
trans,trans-Buta-1,3-diene-1,4-dicarboxylate	Generator
trans-trans-Muconate	Generator
cis,cis-Muconate	MeSH
Muconic acid	MeSH
Muconic acid, (e,e)-isomer	MeSH
trans-beta-Hydromuconic acid	MeSH
1,3-Butadiene-1,4-dicarboxylate	HMDB
1,3-Butadiene-1,4-dicarboxylic acid	HMDB
Hexa-2,4-dienedioate	HMDB
Hexa-2,4-dienedioic acid	HMDB
trans,trans-Muconic acid	HMDB

Chemical Formula

C₆H₆O₄

Average Molecular Weight

142.1094

Monoisotopic Molecular Weight

142.02660868

IUPAC Name

(2E,4E)-hexa-2,4-dienedioic acid

Traditional Name

trans, trans-muconic acid

CAS Registry Number

1119-72-8

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 Key

TXXHDPDFNKHHGW-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

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

muconic acid (CHEBI:27036 )
Dicarboxylic acids (LMFA01170124 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 31026179)

Cellular substructure

Extracellular (HMDB: HMDB0006331)
Membrane (HMDB: HMDB0006331)

Source

Exogenous

Exogenous (HMDB: HMDB0006331)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006331)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.48 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.49	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.93 m³·mol⁻¹	ChemAxon
Polarizability	12.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon