Pyrocatechol

Jump to: navigation, search
Template:Chembox E numberTemplate:Chembox SolubilityInWater
Pyrocatechol
IUPAC name Pyrocatechol
Other names catechol
benzene-1,2-diol
2-hydroxyphenol
α-hydroxyphenol
o-benzenediol
o-hydroxyphenol
1,2-dihydroxybenzene
pyrocatechin
Identifiers
3D model (JSmol)
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
RTECS number UX1050000
Properties
C6H6O2
Molar mass 110.1 g/mol
Appearance white solid
Density 1.344 g/cm³, solid
Melting point
Boiling point
Hazards
EU classification {{{value}}}
R-phrases R21/22, R36/38
S-phrases (S2), S22, S26, S37
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

WikiDoc Resources for Pyrocatechol

Articles

Most recent articles on Pyrocatechol

Most cited articles on Pyrocatechol

Review articles on Pyrocatechol

Articles on Pyrocatechol in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Pyrocatechol

Images of Pyrocatechol

Photos of Pyrocatechol

Podcasts & MP3s on Pyrocatechol

Videos on Pyrocatechol

Evidence Based Medicine

Cochrane Collaboration on Pyrocatechol

Bandolier on Pyrocatechol

TRIP on Pyrocatechol

Clinical Trials

Ongoing Trials on Pyrocatechol at Clinical Trials.gov

Trial results on Pyrocatechol

Clinical Trials on Pyrocatechol at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Pyrocatechol

NICE Guidance on Pyrocatechol

NHS PRODIGY Guidance

FDA on Pyrocatechol

CDC on Pyrocatechol

Books

Books on Pyrocatechol

News

Pyrocatechol in the news

Be alerted to news on Pyrocatechol

News trends on Pyrocatechol

Commentary

Blogs on Pyrocatechol

Definitions

Definitions of Pyrocatechol

Patient Resources / Community

Patient resources on Pyrocatechol

Discussion groups on Pyrocatechol

Patient Handouts on Pyrocatechol

Directions to Hospitals Treating Pyrocatechol

Risk calculators and risk factors for Pyrocatechol

Healthcare Provider Resources

Symptoms of Pyrocatechol

Causes & Risk Factors for Pyrocatechol

Diagnostic studies for Pyrocatechol

Treatment of Pyrocatechol

Continuing Medical Education (CME)

CME Programs on Pyrocatechol

International

Pyrocatechol en Espanol

Pyrocatechol en Francais

Business

Pyrocatechol in the Marketplace

Patents on Pyrocatechol

Experimental / Informatics

List of terms related to Pyrocatechol

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [2] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.


Pyrocatechol, more commonly known as catechol, is a benzenediol, with the formula C6H4(OH)2.

Isolation, synthesis

Catechol was first isolated in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu (Acacia catechu L.f)); it occurs free in kino and in beechwood tar; its sulfonic acid is present in the urine of horse and man.

It results in the alkaline fusion of many resins and may be prepared by fusing ortho-phenolsulphonic acid, o-chlorphenol, o-bromophenol, and o-phenoldisulphonic acid with potash, or, better, by heating its methyl ether, guaiacol, C6H4(OH)(OCH3), a constituent of beechwood tar, with hydriodic acid.

Guaiacol may be obtained directly from beechwood tar, from pyrocatechin by methylation with potash and potassium methyl sulphate at 180, or from anisole by nitration, reduction of the ortho-nitroanisol to amino-anisol, which is then diazotized and boiled with water. It melts at 28 and boils at 250. 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. Guaiacol carbonate is known as duotal, the phosphate as phosphatol, the phosphite as guaiaco-phosphal; phosphotal is a mixture of the phosphites of creosote phenols. The valerianic ester of guaiacol is known as geosote, the henzoic as benzosol, the salicylic as guaiacolsalol, while the glycerin ether appears as guaiamar.

Ferric chloride gives a green coloration with the aqueous solution, whilst the alkaline solution rapidly changes to a green and finally to a black color on exposure to the air. It reduces silver solutions in the cold and alkaline copper on heating.

Catechol readily condenses to form heterocyclic compounds; cyclic esters are formed by phosphorus trichloride and oxychloride, carbonyl chloride, sulphuryl chloride, &c.; whilst ortho-phenylenediamine, o-aminophenol, and o-aminothiophenol give phenazine, phenoxazine and thiodiphenylamine, respectively.

Nomenclature

Pyrocatechol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.[3]

Occurrences

Urushiols are naturally existing organic compounds which have the catechol skeleton structure and diphenol functionality but with alkyl groups substituted onto the aromatic ring. Urushiols are the skin-irritating poisons found in plants like poison ivy, etc. Catecholamines are biochemically significant hormones/neurotransmitters which are phenethylamines where the phenyl group has a catechol skeleton structure. Two parts of a molecule of catechin, another natural compound which is found in tea, have the catechol skeleton structure in them.

Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon exposure to air (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone. This accounts for the browning of cut fruit and vegetables. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Benzoquinone is said to be antimicrobial. which slows the spoilage of wounded fruits and other plant parts. The oxidation of catechol forms quinones and superoxide, which killed 50% of human glioblastoma cells treated with 0.23 mM of this compound in vitro (Pereira et al., 2004).

Uses

Pyrocatechol has been used as a film developing chemical.

Reference

  1. ^ Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2.
  • Barner, B. A. "Catechol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.

Pereira, M.R.G.; de Oliveira, E. S.; de Villar, F. A. G. A.; Grangeiro, M. S.; Fonseca, J.; Silva, A. R.; Costa, M. F. D.; Costa, S. L.; El-Bachá, R. S., Cytotoxicity of catechol towards human glioblastoma cells via superoxide and reactive quinones generation. 2004, J. Bras. Patol. Med. Lab., v. 40, p. 280-285.

See also

References


External links

Cost Effectiveness of Pyrocatechol

| group5 = Clinical Trials Involving Pyrocatechol | list5 = Ongoing Trials on Pyrocatechol at Clinical Trials.govTrial results on PyrocatecholClinical Trials on Pyrocatechol at Google


| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Pyrocatechol | list6 = US National Guidelines Clearinghouse on PyrocatecholNICE Guidance on PyrocatecholNHS PRODIGY GuidanceFDA on PyrocatecholCDC on Pyrocatechol


| group7 = Textbook Information on Pyrocatechol | list7 = Books and Textbook Information on Pyrocatechol


| group8 = Pharmacology Resources on Pyrocatechol | list8 = AND (Dose)}} Dosing of PyrocatecholAND (drug interactions)}} Drug interactions with PyrocatecholAND (side effects)}} Side effects of PyrocatecholAND (Allergy)}} Allergic reactions to PyrocatecholAND (overdose)}} Overdose information on PyrocatecholAND (carcinogenicity)}} Carcinogenicity information on PyrocatecholAND (pregnancy)}} Pyrocatechol in pregnancyAND (pharmacokinetics)}} Pharmacokinetics of Pyrocatechol


| group9 = Genetics, Pharmacogenomics, and Proteinomics of Pyrocatechol | list9 = AND (pharmacogenomics)}} Genetics of PyrocatecholAND (pharmacogenomics)}} Pharmacogenomics of PyrocatecholAND (proteomics)}} Proteomics of Pyrocatechol


| group10 = Newstories on Pyrocatechol | list10 = Pyrocatechol in the newsBe alerted to news on PyrocatecholNews trends on Pyrocatechol


| group11 = Commentary on Pyrocatechol | list11 = Blogs on Pyrocatechol

| group12 = Patient Resources on Pyrocatechol | list12 = Patient resources on PyrocatecholDiscussion groups on PyrocatecholPatient Handouts on PyrocatecholDirections to Hospitals Treating PyrocatecholRisk calculators and risk factors for Pyrocatechol


| group13 = Healthcare Provider Resources on Pyrocatechol | list13 = Symptoms of PyrocatecholCauses & Risk Factors for PyrocatecholDiagnostic studies for PyrocatecholTreatment of Pyrocatechol

| group14 = Continuing Medical Education (CME) Programs on Pyrocatechol | list14 = CME Programs on Pyrocatechol

| group15 = International Resources on Pyrocatechol | list15 = Pyrocatechol en EspanolPyrocatechol en Francais

| group16 = Business Resources on Pyrocatechol | list16 = Pyrocatechol in the MarketplacePatents on Pyrocatechol

| group17 = Informatics Resources on Pyrocatechol | list17 = List of terms related to Pyrocatechol


}}
de:Brenzcatechin lv:Pirokatehīns fi:Katekoli



Linked-in.jpg