ChemFOnt: Showing chemical card for trans-trans-Muconic acid (CFc000001581)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:14 UTC

Chemfont ID

CFc000001581

Molecule Identification

Common Name

trans-trans-Muconic acid

Definition

trans,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

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

3588-17-8

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 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

Blood (HMDB: HMDB0002349)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0002349)

Cell

Hematocyte

Platelet (HMDB: HMDB0002349)

Excreta

Biofluid or Excreta

Urine (PMID: 17095285)
Feces (PMID: 24029555)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002349)

Source

Endogenous

Endogenous (HMDB: HMDB0002349)

Animal

Animal (HMDB: HMDB0002349)

Microbe

Exogenous

Food

Food (HMDB: HMDB0002349)

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)

Exogenous (HMDB: HMDB0002349)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002349)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002349)

Lipid metabolism pathway (HMDB: HMDB0002349)

Cellular process

Cell signaling (HMDB: HMDB0002349)

Biochemical process

Lipid transport (HMDB: HMDB0002349)

Role

Biological role

Energy source (HMDB: HMDB0002349)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002349)

Pharmaceutical industry

Biomarker

Benzene Exposure (MarkerDB: MDB00000390)

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