Katehol

Katehol
Pyrocatechol
Pyrocatechol
Ball-and-stick model
Ball-and-stick model
Nazivi
IUPAC naziv
Benzene-1,2-diol
Drugi nazivi
pirokatehol
1,2-benzenediol
2-hidroksifenol
1,2-dihidroksibenzen
Identifikacija
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.004.025
KEGG[1]
  • Oc1c(O)cccc1
Svojstva
C6H6O2
Molarna masa 110,1 g/mol
Agregatno stanje beli prah
Gustina 1,344 g/cm³, čvrst
Tačka topljenja 105 °C (221 °F; 378 K)
Tačka ključanja 2.455 °C (4.451 °F; 2.728 K)
43 g/100 mL
Kiselost (pKa) 9.5
Opasnosti
štetna materija (Xn)
R-oznake R21/22, R36/38
S-oznake (S2), S22, S26, S37
NFPA 704
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity (yellow): no hazard code
1
2
Tačka paljenja 127 °C
Srodna jedinjenja
Srodne benzendiolna jedinjenja
 Rezorcinol
Hidrohinon
Srodna jedinjenja
 1,2-benzohinon
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
Зелена квачицаДа verifikuj (šta je Зелена квачицаДаRed КрстићНе ?)
Reference infokutije

Katehol (pirokatehol, 1,2-dihidroksibenzen) je organsko jedinjenje sa molekulskom formulom C6H4(OH)2.[4] 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.[5]

Katehol se industrijski proizvodi hidroksilacijom fenola upotrebom vodonik-peroksida:[6]

C6H5OH + H2O2 → C6H4(OH)2 + H2O

Reference

  1. ^ 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. 
  2. ^ 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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  уреди
  3. ^ 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. 
  4. ^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0. 
  5. ^ Zheng, L. T.; Ryu, G. M.; Kwon, B. M.; Lee, W. H.; Suk, K. (24. 6. 2008). „Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: Inhibition of microglial neurotoxicity”. European Journal of Pharmacology. 588 (1): 106—113. PMID 18499097. doi:10.1016/j.ejphar.2008.04.035. ,,}-
  6. ^ 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. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). „Phenol Derivatives”. Ullmann's Encyclopedia of Industrial Chemistry. ISBN 978-3-527-30385-4. doi:10.1002/14356007.a19_313. . Article Online Posting Date: June 15, 2000

Literatura

Spoljašnje veze

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