FComEx: cis,cis-Muconic acid (PC000828)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:57 UTC

Update date

2017-01-19 02:36:37 UTC

FoodComEx ID

PC000828

FoodDB Record

FDB023893

Chemical Information

Name

cis,cis-Muconic acid

Description

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 were formed by 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 1950's 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. [HMDB]

CAS Number

1119-72-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(2Z,4Z)-HEXA-2,4-dienedioate	Generator
(2Z,4Z)-HEXA-2,4-dienedioIC ACID	ChEBI
(Z,Z)-2,4-hexadienedioate	hmdb
(Z,Z)-2,4-hexadienedioic acid	hmdb
2,4-Hexadienedioate	hmdb
2,4-Hexadienedioic acid	hmdb
cis,cis-2,4-Hexadienedioate	hmdb
cis,cis-2,4-Hexadienedioic acid	hmdb
Cis,cis-hexadienedioate	hmdb
Cis,cis-hexadienedioic acid	hmdb
Cis,cis-muconate	hmdb

Chemical Formula

C6H6O4

IUPAC name

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

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

Isomeric SMILES

OC(=O)\C=C\C=C\C(O)=O

Average Molecular Weight

142.1094

Monoisotopic Molecular Weight

142.02660868

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