Showing Compound cis,cis-Muconic acid (FDB023893)

Record Information

Version

1.0

Creation date

2011-09-21 00:36:30 UTC

Update date

2015-10-09 22:32:57 UTC

Primary ID

FDB023893

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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

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Synonym	Source
(2E,4E)-2,4-Hexadienedioate	Generator
(2E,4E)-2,4-Hexadienedioic acid	ChEBI
(2Z,4Z)-HEXA-2,4-dienedioate	Generator
(2Z,4Z)-HEXA-2,4-dienedioIC ACID	ChEBI
(e,e)-2,4-Hexadienedioate	Generator
(e,e)-2,4-Hexadienedioic acid	ChEBI
(e,e)-Muconate	Generator
(e,e)-Muconic acid	ChEBI
(Z,Z)-2,4-hexadienedioate	hmdb
(Z,Z)-2,4-hexadienedioic acid	hmdb

Showing 1 to 10 of 33 entries

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

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

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	trans-trans-Muconic acid, 2 TMS, GC-MS Spectrum	splash10-00di-3950000000-4833ed03fecc5d107087	Spectrum
GC-MS	trans-trans-Muconic acid, non-derivatized, GC-MS Spectrum	splash10-00di-3950000000-4833ed03fecc5d107087	Spectrum
GC-MS	trans-trans-Muconic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0920000000-25984cbefee561769fe3	Spectrum
Predicted GC-MS	trans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0005-9400000000-1d771b996d6b60d97202	Spectrum
Predicted GC-MS	trans-trans-Muconic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dj-8930000000-43cca1649a383c178957	Spectrum
Predicted GC-MS	trans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	trans-trans-Muconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-1900000000-ba0597e9fe553580b776	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004m-9700000000-bb11fdbd4cb83319bdcf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-60049330475bcfa51fdd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-d089e6c88da6929f4c62	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-5900000000-d4f0aa2255b01aabc0bf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fdp-9300000000-bc5a2d5e39f202b87d9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-9600000000-3e5c79b293ac84a6a831	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-b7fce2b042b06e3cb276	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-9000000000-5b8045afa89b9f96b99d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-5b62b2b14bc9b75cd848	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-9000000000-20df0bac53b1a654f39b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-9000000000-e2a3f3d1e8945188e022	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4444151

ChEMBL ID

Not Available

KEGG Compound ID

C02480

Pubchem Compound ID

5280518

Pubchem Substance ID

Not Available

ChEBI ID

16508

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06331

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36677

KNApSAcK ID

Not Available

HET ID

CCU

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound cis,cis-Muconic acid (FDB023893)

Structure for FDB023893 (cis,cis-Muconic acid)