Livestock Metabolome Database: Showing metabocard for Pyrocatechol (LMDB00289)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:33 UTC

Update Date

2018-04-30 21:14:42 UTC

Lmdb

LMDB00289

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyrocatechol

Description

Pyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 oC and boils at 250 oC. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application.

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

[H]OC1=C([H])C([H])=C([H])C([H])=C1O[H]

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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udr-1950000000-16187bb35dcb40c26e78	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-8900000000-4e15f35dca47661de590	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9600000000-032a40483dec93738075	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-7900000000-83f892852c355a3863e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9400000000-90885264baa17f65d954	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udr-1950000000-16187bb35dcb40c26e78	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udr-1930000000-24d2e0a8e36245d9e187	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-7900000000-8b112b8af75eb2d08676	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fl9-9730000000-a35befff1c602124f29e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ox-9400000000-d59dce8c5e56b026f8b2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-632cabc9b371835019c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02t9-9200000000-ac902cb99981017de3b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-03di-8900000000-95af3d2738de98d27f26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-03di-9600000000-032a40483dec93738075	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-03di-7900000000-f5cb1c53768e05ca1530	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-c94dab4d218dbb3bb108	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0a4i-1900000000-edd8ba1e77bbb2f76304	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-c94dab4d218dbb3bb108	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1900000000-edd8ba1e77bbb2f76304	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-12053747e62e910151ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-72e952ea8e487994be54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-19b1bae28f3dfde3323a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-33b2a7e7a951547dfafa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-6e731d4eaba18fcad18f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1900000000-a7c1a830ea96e82252bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3772b2cca96bf4a1b05f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-9531f3e0c85e67d6c6ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-5886b926a1814092c4b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-66523f3122b954e6400f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-5fd776e479836f7464af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-2c46a1375dbb634ef735	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-986c93875cb12d90fa90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-a301685abb4194689ca3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-2017b42835ace86f16ee	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9600000000-b8e03f4f3ea89044828e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum