Catechol, use

Y Tsuji, T. Ohta, T. Ido, H. Minbu, and Y. Watanabe, Ruthenium-catalyzed oxidation of alcohols and catechols using t-butyl hydroperoxide, J. Organometallic Chem. 270(3), 333-341 (1984). 

Figure 15.7 Production of 3-substituted catechols using a designer biocatalyst.

Mechanistic aspects of the intermolecular cyclization reaction in the anodic oxidation of catechol in the presence of 4-hydroxycoumarin were discussed in Sect. 2.2. This reaction is a synthetically simple and versatile method for the preparation of formally [3 + 2] cycloadducts between a -diketo compound and catechol [44,45]. Anodic oxidation of catechol using controlled potential electrolysis (E = 0.9-1.1 V vs SCE) or constant current electrolysis (i = 5 mA/cm ) was performed in water solution containing sodium acetate (0.15 mol/1) in the presence of various nucleophiles such as 4-hydroxycoumarin,... 

Muranaka A, Okuda M, Kobayashi N, Somers K, Ceulemans A (2004) Recognition of chiral catechols using oxo-titanium phthalocyanine. J Am Chem Soc 126(14) 4596-4604... 

Aromatic species which are activated for electrophilic substitution may be hydroxylated in the presence of strong acids. The largest single application of this technology is for the hydroxylation of phenol to hydroquinone and catechol using a mixture of perchloric and phosphoric acids as catalysts.468 As the products are more readily oxidized compared with the substrate, it is important to limit the conversion of the phenol to prevent over-oxidation to tars. 

Increase of pH in the range 0-4 decreases the rate. The pH dependence can be accounted for quantitatively by assuming different reactivities for HsIOg and a periodate monoanion. Kaiser and Weidman later studied the oxidation of catechol using a stopped-flow apparatus, and showed that the reaction proceeded via an intermediate. The formation of the latter was second order, and at pH 1.0 the second-order rate coefficient is expressed by (from measurements at 15° and 25 °C)... 

Holmes C, Eisenhofer G, Goldstein DS. Improved assay for plasma dihydroxyphenylacetic acid and other catechols using high-performance liquid chromatography with electrochemical detection. J Chromatogr B Biomed Appl 1994 653 131-8. 

Kakuchi and Yokota have reported the enantioselective cyclopolymerization of divinyl acetal and divinyl catechol using a chiral cationic initiator 31/ZnCl2 (Scheme 15) [104,105]. The resultant polymer contains only cyclic units, however the relative ratio of cis and trans rings is not reported. By comparing the CD spectra of the polymer and a model compound, it was suggested that the trans rings of the polymer were predominantly of one absolute configuration. 

Table 16.3-6. Preparative-scale production of 3-substituted catechols using E. coli )M101 containing 2-hydroxybiphenyl-3-monooxygenase1141.

S-naphthoyl-toluidine blue O, and 4-[2-(2-naphthoyl)vinyl]catechol) used to modify carbon surfaces for the mediation of NADH oxidation. Each dye molecule has an aromatic substituent attached in order to promote adsorption onto the basal plane regions of graphite through tt-tt interaction. The examples are taken from [30, 31, 33, 34]. 

Write et al. explored direct detection of various phenohc compoimds (phenol, hydroquinone, resorcinol, phloroglucinol, and catechol) using an SPR sensor with intensity modulation and synthetic receptors loaded in a polymer or sol-gel layer [39]. Their preUminary experiments, consisting of the detection of phenols in buffer, suggested that detection of phenols at mUlimolar concentration levels ( 100 iJigmL ) is feasible using this approach. 

Alessio, P., Pavinatto, F.J., Oliveira Junior, O.N., Saez, J.A.S., Constantino, C.J.L., Rodr(guez-M6ndez, M.L. Detection of catechol using mixed Langmuir-Blodgett films of a phospholipid and phthalocyanines as voltammetric sensors. Analyst 135, 2591-1599 (2010). doi 10.1039/c0an00159g... 

Main constituent of the allergenic oil of poison ivy Toxicodendron radicans)y poison oak (T. diversilobum) Asiatic lacquer tree (T. verniciferum D.C.) and other plants of the genera Toxicodendron and Anacardiaceae. A mixture of several compounds which are derivatives of catechol Uses in Japanese lacquer... 

Figure 5. Calibration graph for catechol using (a) HRP and (b) CDH biosensor. The calibration data using HRP are fitted to the Michaelis-Menten equation. For experimental conditions see Figure 3, [H2O2] 100 pM, [cellobiose] 200 pM.

Figure 3 HDVs recorded for dopamine and catechol using end-column detection at cap-illary-to-electrode distances of 20 and 60 pm without (A) and with (B) a fracture decoupler. Symbols dopamine ( ) and catechol ( ) at 20 pm dopamine ( ) and catechol (A) at 60 pm. Open and closed symbols represent different trials. (Reprinted with permission from Ref. 26.)...

Lunsford, S. K., H. Choi, J. Stinson, A. Yeary, and D. D. Dionysiou, 2007. Voltammetric determination of catechol using a sonogel carbon electrode modified with nanostructured titanium dioxide. Talanta 73 172-77. 

DMSO (Castro et al. 2004). All the reactions were sensitive to the amount of the catechol used and less so to the amount of base. Successful reactions were completed in less than 1 h. 

Tembe S, Inamdar S, Haram S, Karve M, D Souza SF (2007) Electrochemical biosensor for catechol using agarose-guar gum entrapped tyrosinase. J Biotechnol 128(l) 80-85. doi 10. 1016/j.jbiotec.2006.09.020... 

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