Katehol

Katehol
Pyrocatechol	Ball-and-stick model
	Benzene-1,2-diol
Drugi nazivi	pirokatehol; 1,2-benzenediol; 2-hidroksifenol; 1,2-dihidroksibenzen
Identifikacija
CAS registarski broj	120-80-9
PubChem	289
ChemSpider	283
KEGG	C00090
ChEMBL	CHEMBL280998
Jmol-3D slike	Slika 1
SMILES
	Oc1c(O)cccc1
InChI
	InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H ; Kod: YCIMNLLNPGFGHC-UHFFFAOYSA-N
Svojstva
Molekulska formula	C6H6O2
Molarna masa	110.1 g/mol
Agregatno stanje	beli prah
Gustina	1.344 g/cm³, čvrst
Tačka topljenja	105 °C, 378 K, 221 °F
Tačka ključanja	245.5 °C, 519 K, 474 °F
Rastvorljivost u vodi	43 g/100 mL
pKa	9.5
Opasnost
EU-klasifikacija	štetna materija (Xn)
NFPA 704	1 2 0
R-oznake	R21/22, R36/38
S-oznake	S2, S22, S26, S37
Tačka paljenja	127 °C
Srodna jedinjenja
Srodna benzendiolna jedinjenja	Rezorcinol; Hidrohinon
Srodna jedinjenja	1,2-benzohinon
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Katehol (pirokatehol, 1,2-dihidroksibenzen) je organsko jedinjenje sa molekulskom formulom C₆H₄(OH)₂.^[6] On je orto izomer benzendiola. Ovo bezbojno jedinjenje se prirodno javlja u veoma malim količinama. Oko 20 miliona kg se proizvodi godišnje, uglavnom kao prekurzor za pesticide, ukuse i mirise

Katehol se javlja u obliku pahuljastih belih kristala koji se veoma brzo rastvaraju u vidi.

Ime „katehol“ se takođe koristi za klasu hemijskih jedinjenja, koja su još poznata kao katehini.

Izolacija i sinteza

Katehol je prvi put izolovao 1839. H. Reinsch putem distilacije katehina iz katišua, ekstrakta biljke Mimosa catechu. Nakon zagrejavanja katehina iznad tačke razlaganja, supstanca prvo poznata kao "pirokatehol" (kasnije jednostavno katehol) je formirana. Katehol se prirodno javlja u tri oblika u biljci Pterocarpus marsupium, u katranu bukvinog drveta, i njegova sulfonska kiselina je detektovana u urinu konja i ljudi.^[7]

Katehol se industrijski proizvodi hidroksilacijom fenola upotrebom vodonik-peroksida:^[8]

C₆H₅OH + H₂O₂ → C₆H₄(OH)₂ + H₂O

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
↑ Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: Inhibition of microglial neurotoxicity. European Journal of Pharmacology, Volume 588, Issue 1, 24 June 2008, Pages 106-113
↑ Helmut Fiegel, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002: Weinheim. DOI: 10.1002/14356007.a19_313. Article Online Posting Date: June 15, 2000

Vanjske veze

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[Clayden1st-6] Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.

[7] Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: Inhibition of microglial neurotoxicity. European Journal of Pharmacology, Volume 588, Issue 1, 24 June 2008, Pages 106-113

[Ullmann-8] Helmut Fiegel, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002: Weinheim. DOI: 10.1002/14356007.a19_313. Article Online Posting Date: June 15, 2000

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