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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-10-17 22:47:59 UTC
HMDB IDHMDB00957
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyrocatechol
DescriptionPyrocatechol, 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
Thumb
Synonyms
ValueSource
1,2-DihydroxybenzeneHMDB
2-HydroxyphenolHMDB
CatecholHMDB
Durafur developer CHMDB
Fouramine PCHHMDB
Fourrine 68HMDB
O-BenzenediolHMDB
O-DihydroxybenzeneHMDB
O-DioxybenzeneHMDB
O-HydroquinoneHMDB
O-HydroxyphenolHMDB
O-PhenylenediolHMDB
OxyphenateHMDB
Oxyphenic acidHMDB
Pelagol grey CHMDB
PhthalhydroquinoneHMDB
Phthalic alcoholHMDB
PyrocatechinHMDB
PyrocatechineHMDB
Chemical FormulaC6H6O2
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
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 KeyInChIKey=YCIMNLLNPGFGHC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatechols
Alternative Parents
Substituents
  • 1,2-diphenol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Prostaglandin and leukotriene metabolism
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point105 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility461.0 mg/mLNot Available
LogP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility75.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m3·mol-1ChemAxon
Polarizability10.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udr-1950000000-16187bb35dcb40c26e78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9400000000-d59dce8c5e56b026f8b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-632cabc9b371835019c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9200000000-ac902cb99981017de3b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-8900000000-95af3d2738de98d27f26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-03di-9600000000-032a40483dec93738075View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-7900000000-f5cb1c53768e05ca1530View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb108View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f76304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-66523f3122b954e6400fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-5fd776e479836f7464afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-2c46a1375dbb634ef735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-986c93875cb12d90fa90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-a301685abb4194689ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-2017b42835ace86f16eeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-b8e03f4f3ea89044828eView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Bone Marrow
  • Brain
  • Intestine
  • Liver
  • Neuron
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.665 +/- 0.093 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.027 +/- 2.529 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.269 +/- 2.507 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.673 +/- 1.103 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.677 +/- 0.177 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.666 +/- 0.17 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.612 +/- 0.101 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.714 +/- 0.201 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified8.900 +/- 2.270 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10.353 +/- 4.995 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified20.434 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
FecesDetected and Quantified8.900 +/- 2.270 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10.353 +/- 4.995 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified20.434 nmol/g of fecesAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified4.06 +/- 1.80 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified6.0 +/- 4.3 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.7 (2.0-8.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 654
  • Not Applicable
details
UrineDetected and Quantified13.9 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.585 +/- 0.224 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [22024767 ]
Associated OMIM IDs
DrugBank IDDB02232
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID654
Phenol Explorer Metabolite ID654
FoodDB IDFDB001512
KNApSAcK IDC00002644
Chemspider ID13837760
KEGG Compound IDC00090
BioCyc IDCATECHOL
BiGG IDNot Available
Wikipedia LinkPyrocatechol
NuGOwiki LinkHMDB00957
Metagene LinkHMDB00957
METLIN ID282
PubChem Compound289
PDB IDCAQ
ChEBI ID18135
References
Synthesis ReferenceLauterbach, 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)Download (PDF)
General References
  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. [16573647 ]
  2. Nguyen SD, Sok DE: Effect of 3,4-dihydroxyphenylalanine on Cu(2+)-induced inactivation of HDL-associated paraoxonasel and oxidation of HDL; inactivation of paraoxonasel activity independent of HDL lipid oxidation. Free Radic Res. 2004 Sep;38(9):969-76. [15621715 ]
  3. Kiso Y: Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study. Biofactors. 2004;21(1-4):191-6. [15630196 ]
  4. Rivest J, Barclay CL, Suchowersky O: COMT inhibitors in Parkinson's disease. Can J Neurol Sci. 1999 Aug;26 Suppl 2:S34-8. [10451758 ]
  5. Goodall M, Diddle AW: Epinephrine and norepinephrine in pregnancy. A comparative study of the adrenal gland and catechol output in different species of animals and man. Am J Obstet Gynecol. 1971 Dec 1;111(7):896-904. [5118028 ]
  6. Olanow CW, Obeso JA: Pulsatile stimulation of dopamine receptors and levodopa-induced motor complications in Parkinson's disease: implications for the early use of COMT inhibitors. Neurology. 2000;55(11 Suppl 4):S72-7; discussion S78-81. [11147513 ]
  7. Zand R, Nelson SD, Slattery JT, Thummel KE, Kalhorn TF, Adams SP, Wright JM: Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther. 1993 Aug;54(2):142-9. [8354023 ]
  8. Swaminath G, Deupi X, Lee TW, Zhu W, Thian FS, Kobilka TS, Kobilka B: Probing the beta2 adrenoceptor binding site with catechol reveals differences in binding and activation by agonists and partial agonists. J Biol Chem. 2005 Jun 10;280(23):22165-71. Epub 2005 Apr 7. [15817484 ]
  9. Goldstein DS, Holmes C, Kaufmann H, Freeman R: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure. Clin Auton Res. 2004 Dec;14(6):363-8. [15666063 ]
  10. Schapira AH, Obeso JA, Olanow CW: The place of COMT inhibitors in the armamentarium of drugs for the treatment of Parkinson's disease. Neurology. 2000;55(11 Suppl 4):S65-8; discussion S69-71. [11147512 ]
  11. Purba HS, Maggs JL, Orme ML, Back DJ, Park BK: The metabolism of 17 alpha-ethinyloestradiol by human liver microsomes: formation of catechol and chemically reactive metabolites. Br J Clin Pharmacol. 1987 Apr;23(4):447-53. [3555579 ]
  12. Moretti M, Villarini M, Simonucci S, Fatigoni C, Scassellati-Sforzolini G, Monarca S, Pasquini R, Angelucci M, Strappini M: Effects of co-exposure to extremely low frequency (ELF) magnetic fields and benzene or benzene metabolites determined in vitro by the alkaline comet assay. Toxicol Lett. 2005 Jun 17;157(2):119-28. [15836999 ]
  13. Poupaert J, Carato P, Colacino E, Yous S: 2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes. Curr Med Chem. 2005;12(7):877-85. [15853716 ]
  14. Mosca L, Lendaro E, d'Erme M, Marcellini S, Moretti S, Rosei MA: 5-S-Cysteinyl-dopamine effect on the human dopaminergic neuroblastoma cell line SH-SY5Y. Neurochem Int. 2006 Aug;49(3):262-9. Epub 2006 Mar 20. [16549224 ]
  15. Santens P: Sleep attacks in Parkinson's disease induced by Entacapone, a COMT-inhibitor. Fundam Clin Pharmacol. 2003 Feb;17(1):121-3. [12588639 ]
  16. Cavalieri EL, Rogan EG, Chakravarti D: Initiation of cancer and other diseases by catechol ortho-quinones: a unifying mechanism. Cell Mol Life Sci. 2002 Apr;59(4):665-81. [12022473 ]
  17. Relling MV, Nemec J, Schuetz EG, Schuetz JD, Gonzalez FJ, Korzekwa KR: O-demethylation of epipodophyllotoxins is catalyzed by human cytochrome P450 3A4. Mol Pharmacol. 1994 Feb;45(2):352-8. [8114683 ]
  18. Irons RD: Quinones as toxic metabolites of benzene. J Toxicol Environ Health. 1985;16(5):673-8. [4093989 ]
  19. Luffer-Atlas D, Vincent SH, Painter SK, Arison BH, Stearns RA, Chiu SH: Orally active inhibitors of human leukocyte elastase. III. Identification and characterization of metabolites of L-694,458 by liquid chromatography-tandem mass spectrometry. Drug Metab Dispos. 1997 Aug;25(8):940-52. [9280402 ]
  20. Munns AJ, De Voss JJ, Hooper WD, Dickinson RG, Gillam EM: Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem Res Toxicol. 1997 Sep;10(9):1049-58. [9305589 ]

Enzymes

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
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
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
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
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
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
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
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
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
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