• Title/Summary/Keyword: Phenol analogues

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Catalytic Oxidation of Phenol Analogues in Aqueous Medium Over Fe/SBA-15

  • Mayani, Suranjana V.;Mayani, Vishal J.;Kim, Sang-Wook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.3009-3016
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    • 2012
  • This study evaluated the use of iron-impregnated SBA-15 (Fe/SBA-15) as a catalyst for the oxidative degradation of persistent phenol analogues, such as 2-chlorophenol (2-CP), 4-chlorophenol (4-CP), 2-nitrophenol (2-NP), 4-nitrophenol (4-NP) and 2,4,6-trichlorophenol (2,4,6-TCP) in water. The oxidation reactions were carried out with reaction time, concentration of the phenols, amount of the catalysts, reaction temperature, pH of the reaction mixture as the process variables with or without using hydrogen peroxide as the oxidizing agent. The conversion achieved with Fe/SBA-15 at 353 K for 2-CP, 4-CP, 2-NP, 4-NP, 2,4,6-TCP was 80.2, 71.2, 53.1, 62.8, 77.3% in 5h with a reactant to $H_2O_2$ mole ratio of 1:1, and 85.7, 65.8, 61.9, 63.7, 78.1% in the absence of $H_2O_2$, respectively. The reactions followed pseudo first order kinetics. The leachability study indicated that the catalyst released very little iron into water and therefore, the possibility of secondary pollution is negligible.

Bisphenol A and the related alkylphenol contaminants in crustaceans and their potential bioeffects

  • Zuo, Yuegang;Zhu, Zhuo;Alshanqiti, Mohammed;Michael, Joseph;Deng, Yiwei
    • Advances in environmental research
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    • v.4 no.1
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    • pp.39-48
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    • 2015
  • Bisphenol A is widely used in plastic and other industrial consumer products. Release of bisphenol A and its analogues into the aquatic environment during manufacture, use and disposal has been a great scientific and public concern due to their toxicity and endocrine disrupting effects on aquatic wildlife and even human beings. More recent studies have shown that these alkylphenols may affect the molting processes and survival of crustacean species such as American lobster, crab and shrimp. In this study, we have developed gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometric (GC-MS) methods for the determination of bisphenol A and its analogues in shrimp Macrobrachium rosenbergii, blue crab Callinectes sapidus and American lobster Homarus americanus samples. Bisphenol A, 2,4-bis-(dimethylbenzyl)phenol and 4-cumylphenol were found in shrimp in the concentration ranges of 0.67-5.51, 0.36-1.61, and < LOD (the limit of detection)-1.96 ng/g (wet weight), and in crab of 0.10-0.44, 0.13-0.62, and 0.26-0.58 ng/g (wet weight), respectively. In lobster tissue samples, bisphenol A, 2-t-butyl-4-(dimethylbenzyl)phenol, 2,6-bis-(t-butyl)-4-(dimethylbenzyl)phenol, 2,4-bis-(dimethybenzyl)phenol, 2,4-bis-(dimethylbenzyl)-6-t-butylphenol and 4-cumylphenol were determined at the concentration ranges of 4.48-7.01, 1.23-2.63, 2.71-9.10, 0.35-0.91, 0.64-3.25, and 0.44-1.00 ng/g (wet weight), respectively. At these concentration levels, BPA and its analogs may interfere the reproduction and development of crustaceans, such as larval survival, molting, metamorphosis and shell hardening.

Inhibitory Activity of 8-Aminowogonin Analogues Against Prostaglandin $E_2$ Production (8-아미노우고닌 유도체의 Prostaglandin $E_2$ 생성에 대한 저해작용)

  • Jang, Jin-Hee;Sin, Kwan-Seog;Kim, Hyun-Pyo;Park, Hae-Il
    • YAKHAK HOEJI
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    • v.52 no.1
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    • pp.85-91
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    • 2008
  • 8-Acyl and 8-sulfonylamidowogonin analogues were synthesized as potential anti-inflammatory agents. Nitration of 5,7-dihydroxyflavone (chrysin) followed by methylation of phenol groups and reduction of nitro group yielded 8-aminowogonin analogues. Acylation and sufonylation of 8-aminowogonin followed by demethylation reactions gave the title compunds. The synthesized wogonin analogues showed much reduced inhibitory activity on prostaglandin $E_2\;(PGE_2)$ production.

Visible and Fast Assay System for Tobacco Transformant Introduced with Adenosine Deaminase Marker Gene (Adenosine Deaminase 표지유전자로 형질전환된 연초의 신속한 Assay 방법)

  • 양덕춘;김용환;임학태;방극수;배창휴
    • Korean Journal of Plant Tissue Culture
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    • v.28 no.3
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    • pp.165-171
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    • 2001
  • New visible and fast assay system have been developed for tobacco transformant introduced with adenosine deaminase (ADA) marker gene, which converts cytotoxic adenosine analogues to non-toxic inosine analogues and ammonia. Ammonia was changed to blue color in the solution of phenol-nitoprusside and alkaline-hypochlorite. It was possible to detect activity of ADA visibly on the holes of 96 well plate using tiny explant of transgenic tobacco leaves within 1 hour incubation time. As substrates of ADA enzyme from transgenic plant on the plate, a number of adenosine analogues such as 9-D-arabinofuranosyl adenine, cordycepin, 2'-deoxyadenosine, adenosine and xylofuranosyl adenine were possible for detection of ADA activity. Optimal condition of substrate for ADA enzyme was each 10 mM and pH 7.5 in adenosine solution. Especially, transgenic plant did not convert adenosine to inosine and ammonia in the presence of ADA inhibitor deoxycoformycin, which means that ammonia produced from transgenic plant is due to expression of ADA gene. Now, we show that this detection system can be easily, sensitively, fast and cheaply as well as visibly assayed in vitro as GUS gene system with very small size of transformant explant.

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3D-QSAR Analyses on the Inhibition Activity of 4-($R_1$)-Benzyl Alcohol and 4-($R_2$)-Phenol Analogues Against Tyrosinase (4-($R_1$)-Benzyl alcohol 및 4-($R_2$)-Phenol 유도체들의 Tyrosinase 활성 저해에 대한 3D-QSAR 분석)

  • Kim, Sang-Jin;Lee, Myoung-Hee
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.35 no.4
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    • pp.271-276
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    • 2009
  • The 3-dimensional quantitative structure-activity relationships (3D-QSARs) models between the substituents with changing groups ($R_1$ & $R_2$) of 4-($R_1$)-benzyl alcohol and 4-($R_2$)-phenol derivatives as substrate molecule and their inhibitory activities against tyrosinase were derived and discussed quantitatively. The optimized CoMSIA 2 model have best predictability and fitness ($r^2\;=\;0.858$ & $q^2\;=\;0.951$). The contour maps of optimized CoMSIA 2 model showed that, the inhibitory activities of the analogues against tyrosinase were expected to increase when hydrophobic favor, negative charge favor, steric disfavor and hydrogen bond donor disfavor groups were substituted at the $R^2$ position. When the positive charge and the hydrogen bond donor favor groups were substituted at the $R_1$ position, it is predicted that the substituents will be able to increase the inhibitory activity. However, hydrogen bond acceptor did not affect inhibitory activities of tyrosinase.

Transmission Substituent Effects through Five-Membered Heteroaromatic Rigns, Ⅱ. Deprotonation Equilibra of Phenol Analogues

  • Son, Chang Guk;Im, Seon Hui;Ri, Sun Gi;Kim, Chang Gon;Kim, Chan Gyeong;Lee, Ik Hun
    • Bulletin of the Korean Chemical Society
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    • v.21 no.9
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    • pp.891-895
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    • 2000
  • Transmission of substituent effects through 5-membered heteroaromaticrings isinvestigated theoretically at the RHF/6-31+G* and B3LYP/6-31+G* levelsusing the deprotonation equilibria of phenol analogues with heteroatoms Y = NH, O, PHand S. The incr ease in the resonance delocalization of the $\pilone-pair$ on the phe-nolic oxygen atom, $n\pi(O)$, accompanied with the deprotonation depends on the heteroatom Y,in the order NH < O < PH < S. This represents the $\pielectron$ accepting ability, or conversely reverse order of the $\pielectron$ donating ability of the $\pilone-pair$ on Y, $n\pi(Y).$ The transmission efficiency of substituenteffects is, however,in the reverse order NH > O > S, which represents the order of delocalizability of $n\pi(Y).$ A better correlation is obtained with ${\sigma}p$ - than with ${\sigma}p$ for the Hammett type plots with the positive slope, $\rho-$ > 0, of the magnitude in the same order as that for the delocalizability of $n\pi(Y).$ Thedeprotonation energy, ΔG = [G(PA) + G(H+)] -G(P), decreases with the increasein the extence delocalization in the order NH > O > PH > S.

Development of an ELISA for the Organophosphorus Insecticide Isofenphos

  • Park, Han-Jin;Park, Won-Chul;Jung, Tae-Owan;Rha, Choon-Sup;Lee, Yong-Tae
    • Bulletin of the Korean Chemical Society
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    • v.23 no.4
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    • pp.599-603
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    • 2002
  • A selective enzyme-linked immunosorbent assay (ELISA) for the insecticide isofenphos was developed. Three different analogues (haptens) of isofenphos were synthesized and were coupled to carrier proteins through the pesticide thiophosphate group t o use as immunogens or coating antigens. Rabbits were immunized with one of the haptens coupled to BSA for production of polyclonal antibodies and the sera were screened against each of the other two haptens coupled to ovalbumin (OVA). Using the sera of highest specificity, an antigen-coated ELISA was developed, which showed an I50 of 96 ng/mL with the detection limit of 2 ng/mL. The antibodies showed negligible cross-reactivity with other organophosphorus pesticides and the phenol metabolite of isofenphos, which makes the developed assay suitable for the selective detection of isofenphos. An antibody-coated ELISA was also developed, which showed an I50 of 580 ng/mL with a detection limit of 70 ng/mL.