Bovine Metabolome Database: Showing metabocard for Pyrocatechol (BMDB0000957)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:39:07 UTC

Update Date

2020-05-19 22:01:22 UTC

BMDB ID

BMDB0000957

Secondary Accession Numbers

BMDB00957

Metabolite Identification

Common Name

Pyrocatechol

Description

Pyrocatechol, also known as 1,2-benzenediol or 2-hydroxyphenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Pyrocatechol exists in all living organisms, ranging from bacteria to humans. Pyrocatechol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Benzenediol	ChEBI
1,2-Dihydroxybenzene	ChEBI
2-Hydroxyphenol	ChEBI
alpha-Hydroxyphenol	ChEBI
Brenzcatechin	ChEBI
O-Benzenediol	ChEBI
O-Hydroxyphenol	ChEBI
Pyrocatechin	ChEBI
a-Hydroxyphenol	Generator
Α-hydroxyphenol	Generator
Catechol	HMDB
Durafur developer C	HMDB
Fouramine PCH	HMDB
Fourrine 68	HMDB
O-Dihydroxybenzene	HMDB
O-Dioxybenzene	HMDB
O-Hydroquinone	HMDB
O-Phenylenediol	HMDB
Oxyphenate	HMDB
Oxyphenic acid	HMDB
Pelagol grey C	HMDB
Phthalhydroquinone	HMDB
Phthalic alcohol	HMDB
Pyrocatechine	HMDB
1,3-Dihydroxybenzene	HMDB
Catechol dipotassium salt	HMDB
Catechol, 14C-labeled CPD	HMDB
Catechol sodium salt	HMDB
Benzene-1,2-diol	PhytoBank
Pyrocatechol	PhytoBank
1,2-Hydroxybenzene	PhytoBank

Chemical Formula

C₆H₆O₂

Average Molecular Weight

110.1106

Monoisotopic Molecular Weight

110.036779436

IUPAC Name

benzene-1,2-diol

Traditional Name

catechol

CAS Registry Number

120-80-9

SMILES

OC1=CC=CC=C1O

InChI Identifier

InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H

InChI Key

YCIMNLLNPGFGHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:18135 )
a catechol (CATECHOL )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	105 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	461.0 mg/mL	Not Available
LogP	0.88	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.74	ALOGPS
logP	1.37	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.02 m³·mol⁻¹	ChemAxon
Polarizability	10.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Adipose Tissue
Adrenal Gland
Bone Marrow
Brain
Intestine
Liver
Milk
Neuron
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Bone Marrow	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28306241	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000957

DrugBank ID

DB02232

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Catechol

METLIN ID

282

PubChem Compound

289

PDB ID

Not Available

ChEBI ID

18135

References

Synthesis Reference

Lauterbach, Manfred; Zimmermann, Volker; Jaeger, Guenter; Radig, Wolfram; Adam, Johannes; Blady, Regina. Extraction and purification of pyrocatechol. Ger. (East) (1986), 4 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

General function:: Involved in binding
Specific function:: Not Available
Gene Name:: DHDH
Uniprot ID:: Q148L6
Molecular weight:: 36583.0

Enzyme Details

2. Catechol O-methyltransferase

General function:: Involved in catechol O-methyltransferase activity
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:: COMT
Uniprot ID:: A7MBI7
Molecular weight:: 30485.0

Reactions

Norepinephrine + Guaiacol → Normetanephrine + Pyrocatechol	details
Epinephrine + Guaiacol → Metanephrine + Pyrocatechol	details
3,4-Dihydroxyphenylglycol + Guaiacol → Vanylglycol + Pyrocatechol	details
3,4-Dihydroxymandelic acid + Guaiacol → Vanillylmandelic acid + Pyrocatechol	details
Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatechol	details
3,4-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatechol	details

Showing metabocard for Pyrocatechol (BMDB0000957)

Structure for BMDB0000957 (Pyrocatechol)

Enzymes

Reactions