Showing Compound Card for Pyrocatechol (CDB004873)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (9)transporters (1) Show 14 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:45:37 UTC
Updated at2021-01-04 18:59:17 UTC
CannabisDB IDCDB004873
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePyrocatechol
DescriptionPyrocatechol, or o-Benzenediol, often known as catechol or benzene-1,2-diol, is a benzenediol. It belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol is one of three known isomers of benzenediol including o-Benzenediol (Catechol), m-benzenediol (Resorcinol) and p-benzenediol (Hydroquinone). Pyrocatechol exists as white crystals and is very soluble in water. It is also soluble in pyridine and other organic solvents such as chloroform, benzene, CCl4, ether, and ethyl acetate. Pyrocatechol 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. 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 is produced industrially by the hydroxylation of phenol using hydrogen peroxide ( Ref:DOI ). Catechol is used 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. Its sulfonic acid is often present in the urine of many mammals (PMID: 18499097 ). Pyrocatechol has also been found to be a microbial metabolite in Escherichia, Mycobacterium and Pseudomonas (PMID: 19300498 ; PMID: 25281236 ). Catechol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-BenzenediolChEBI
1,2-DihydroxybenzeneChEBI
2-HydroxyphenolChEBI
alpha-HydroxyphenolChEBI
BrenzcatechinChEBI
O-BenzenediolChEBI
O-HydroxyphenolChEBI
PyrocatechinChEBI
a-HydroxyphenolGenerator
Α-hydroxyphenolGenerator
CatecholHMDB
Durafur developer CHMDB
Fouramine PCHHMDB
Fourrine 68HMDB
O-DihydroxybenzeneHMDB
O-DioxybenzeneHMDB
O-HydroquinoneHMDB
O-PhenylenediolHMDB
OxyphenateHMDB
Oxyphenic acidHMDB
Pelagol grey CHMDB
PhthalhydroquinoneHMDB
Phthalic alcoholHMDB
PyrocatechineHMDB
1,3-DihydroxybenzeneHMDB
Catechol dipotassium saltHMDB
Catechol, 14C-labeled CPDHMDB
Catechol sodium saltHMDB
Benzene-1,2-diolPhytoBank
PyrocatecholPhytoBank
1,2-HydroxybenzenePhytoBank
Chemical FormulaC6H6O2
Average Molecular Weight110.11
Monoisotopic Molecular Weight110.0368
IUPAC Namebenzene-1,2-diol
Traditional Namecatechol
CAS Registry Number120-80-9
SMILES
OC1=CC=CC=C1O
InChI Identifier
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChI KeyYCIMNLLNPGFGHC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point105 °CNot Available
Boiling Point245.5 °CWikipedia
Water Solubility461 mg/mLNot Available
logP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.74ALOGPS
logP1.37ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability10.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-b8e03f4f3ea89044828e2014-09-20View Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-0udr-1950000000-16187bb35dcb40c26e78Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-4e15f35dca47661de590Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-03di-9600000000-032a40483dec93738075Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-83f892852c355a3863e9Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-03di-9400000000-90885264baa17f65d954Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-0udr-1950000000-16187bb35dcb40c26e78Spectrum
GC-MSPyrocatechol, non-derivatized, GC-MS Spectrumsplash10-0udr-1930000000-24d2e0a8e36245d9e187Spectrum
Predicted GC-MSPyrocatechol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-7900000000-8b112b8af75eb2d08676Spectrum
Predicted GC-MSPyrocatechol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl9-9730000000-a35befff1c602124f29eSpectrum
Predicted GC-MSPyrocatechol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrocatechol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrocatechol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrocatechol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrocatechol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9400000000-d59dce8c5e56b026f8b22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-632cabc9b371835019c12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9200000000-ac902cb99981017de3b52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-8900000000-95af3d2738de98d27f262012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-03di-9600000000-032a40483dec937380752012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-7900000000-f5cb1c53768e05ca15302012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb1082012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f763042012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb1082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f763042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-12053747e62e910151ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-72e952ea8e487994be542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-19b1bae28f3dfde3323a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-33b2a7e7a951547dfafa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-6e731d4eaba18fcad18f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-a7c1a830ea96e82252bf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3772b2cca96bf4a1b05f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9531f3e0c85e67d6c6ed2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-5886b926a1814092c4b12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-66523f3122b954e6400f2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-5fd776e479836f7464af2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-2c46a1375dbb634ef7352015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-986c93875cb12d90fa902015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-a301685abb4194689ca32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-2017b42835ace86f16ee2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldo-keto reductase family 1 member C4AKR1C410p15.1P17516 details
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Sulfotransferase 1A3/1A4SULT1A316p11.2P50224 details
Aldo-keto reductase family 1 member C3AKR1C310p15-p14P42330 details
Aldo-keto reductase family 1 member C1AKR1C110p15-p14Q04828 details
Aldo-keto reductase family 1 member C2AKR1C210p15-p14P52895 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseDHDH19q13.3Q9UQ10 details
Transmembrane O-methyltransferaseLRTOMT11q13.4Q8WZ04 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Aldo-keto reductase family 1 member C4AKR1C410p15.1P17516 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Aldo-keto reductase family 1 member C3AKR1C310p15-p14P42330 details
Aldo-keto reductase family 1 member C2AKR1C210p15-p14P52895 details
Transmembrane O-methyltransferaseLRTOMT11q13.4Q8WZ04 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000957
DrugBank IDDB02232
Phenol Explorer Compound ID654
FoodDB IDFDB001512
KNApSAcK IDC00002644
Chemspider ID13837760
KEGG Compound IDC15571
BioCyc IDCATECHOL
BiGG IDNot Available
Wikipedia LinkCatechol
METLIN ID282
PubChem Compound289
PDB IDNot Available
ChEBI ID18135
References
General References
  1. Zheng LT, Ryu GM, Kwon BM, Lee WH, Suk K: Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: inhibition of microglial neurotoxicity. Eur J Pharmacol. 2008 Jun 24;588(1):106-13. doi: 10.1016/j.ejphar.2008.04.035. Epub 2008 Apr 18. [PubMed:18499097 ]
  2. Yam KC, D'Angelo I, Kalscheuer R, Zhu H, Wang JX, Snieckus V, Ly LH, Converse PJ, Jacobs WR Jr, Strynadka N, Eltis LD: Studies of a ring-cleaving dioxygenase illuminate the role of cholesterol metabolism in the pathogenesis of Mycobacterium tuberculosis. PLoS Pathog. 2009 Mar;5(3):e1000344. doi: 10.1371/journal.ppat.1000344. Epub 2009 Mar 20. [PubMed:19300498 ]
  3. Balderas-Hernandez VE, Trevino-Quintanilla LG, Hernandez-Chavez G, Martinez A, Bolivar F, Gosset G: Catechol biosynthesis from glucose in Escherichia coli anthranilate-overproducer strains by heterologous expression of anthranilate 1,2-dioxygenase from Pseudomonas aeruginosa PAO1. Microb Cell Fact. 2014 Oct 4;13:136. doi: 10.1186/s12934-014-0136-x. [PubMed:25281236 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show All

Enzymes

Enzyme Details
1. Aldo-keto reductase family 1 member C4
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Enzyme Details
2. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
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.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Enzyme Details
3. Sulfotransferase 1A3/1A4
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P50224
Molecular weight:
34195.96
Enzyme Details
4. Aldo-keto reductase family 1 member C3
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Enzyme Details
5. Aldo-keto reductase family 1 member C1
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Enzyme Details
6. Aldo-keto reductase family 1 member C2
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Enzyme Details
7. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Enzyme Details
8. Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Enzyme Details
9. Transmembrane O-methyltransferase
General function:
Involved in O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones (By similarity). Required for auditory function.
Gene Name:
LRTOMT
Uniprot ID:
Q8WZ04
Molecular weight:
32154.43

Transporters

Enzyme Details
1. Aldo-keto reductase family 1 member C4
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57

Only showing the first 10 proteins. There are 14 proteins in total.

Show All