• Title/Summary/Keyword: 2-Isopropylphenol

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Synthesis and Phytopathogenic Activities of Isopropylphenyl Derivatives (Isopropylphenyl 유도체들의 합성과 식물병원균에 대한 항균활성)

  • Jang, Do-Yeon;Choi, Kyoung-Gil;Lee, Byung-Ho;Kim, Tae-Jun;Jung, Bong-Jin;Choi, Won-Sik
    • Applied Biological Chemistry
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    • v.50 no.3
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    • pp.178-186
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    • 2007
  • 42 compounds such as ester, sulfonyl ester, phosphoyl ester and ether derivatives of 4-isopropylphenol (I) and 2-isopropylphenol (II) were synthesized. These derivatives were identified by IR, GC/MS and $^{1}H-NMR$ spectra. Their in vitro antifungal activities were tested against 10 plant pathogenic fungi. Among them, several compounds showed potent in vitro antifungal activity. The selected compounds showing potent in vitro antifungal activity were tested for their in vivo antifungal acitvities against 5 plant diseases such as rice blast, rice sheath blast, cucumber anthracnose, cucumber gray mold and tomato late blight. As a result, 2-isopropylphenyl piperonyloate (II-7a) showed a potent in vivo antifungal activity against cucumber anthracnose and tomato late blight, 4-isopropylphenyl 4-methoxybenzenesulfonate (I-6b) effectively inhibited the development of rice blast.

Synthesis and Phytophathogenic Activities of Isopropylmethylphenyl benzenesulfonate Derivatives (Isopropylmethylphenyl benzenesulfonate 유도체의 합성과 식물병원균에 대한 생리활성)

  • Choi, Won-Sik;Nam, Seok-Woo;Kim, Hak-Cheun
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.11 no.12
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    • pp.4854-4862
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    • 2010
  • Twenty five compounds isopropylmethylphenyl benzenesulfonate derivatives of thymol (1), 4-isopropyl-3-methylphenol (2), 5-isopropyl-3-methylphenol (3), 4-isopropylphenol (4), and 2-isopropylphenol (5) derivatives were synthesized. These compounds were analyzed for their structural confirmation with IR, GC/MS, and $^1H$-NMR. Synthetic compounds were tested against phytopathogenic fungi activities such as Pyrcularia grisea, Rhizoctonia solani, Phytophthora infestans, Colletotrichum orbiculare, and Sphaerotheca fusca. 2-Isopropyl-5-methylphenyl o-toluenesulfonate (1a), 2-isopropylphenyl 2,4,5-trichloro-benzenesulfonate (5b) and 2-isopropylphenyl 2-methyl-5-nitrobenzenesulfonate (5e) showed a potent in vivo antifungal activity against Pyrcularia grisea, Phytophthora infestans and Sphaerotheca fusca.

Acute toxicity of four alkylphenols (3-tert-butyl-, 2-isopropyl-, 3-propropyl-, and 4-isopropyl-phenol) and their binary mixtures to Microtox, with comparisons to Ceriodaphnia dubia and Pimephales promelas

  • Park, Kyungho;Leonard I. Sweet;Brian E. Olseski;Peter G. Meier
    • Proceedings of the Korean Environmental Health Society Conference
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    • 2003.06a
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    • pp.158-161
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    • 2003
  • Toxicity evaluations of 3-tert-butyl-, 2-isopropyl-, 3-isopropyl- and 4-propyl-phenol and their binary mixtures were performed with the Microtox$\^$(R) / assay and compared to invertebrates and fish. The single chemical, 4-isopropylphenol, exhibited the greatest relative toxicity to the Microtox organism (Vibrio fischeri). The relative electrophilicity (LUMO) of the phenols, in contrast to the lipophilicity (Log P), was strongly correlated with toxicity to V fischeri (r$^2$=0.96, p<0.01). In contrast, relative electrophilicity alone could not explain variances in toxicity of the phenols to Ceriodaphnia dubia. Results suggest that electrophilicity in conjunction with lipophilicity provide better correlation with toxicity to C. dubia and Pimephales promelas. Microtox results from the binary mixture toxicity tests of selected phenolics indicate a mechanism of interaction governed by suppression/antagonism.

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Apoptotic Potential and Chemical Composition of Jordanian Propolis Extract against Different Cancer Cell Lines

  • Abutaha, Nael
    • Journal of Microbiology and Biotechnology
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    • v.30 no.6
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    • pp.893-902
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    • 2020
  • Propolis is a resinous substance that is collected by Apis mellifera from plant sources and is used in traditional medicine. To study the phytochemical constituents and apoptotic potential of Jordanian propolis extract against different cancer cell lines, propolis was extracted using methanol, hexane, and ethyl acetate and was fractionated using chromatographic methods. Cytotoxicity was assessed using MTT and LDH assays. The apoptotic potential was investigated using florescence microscopy, multicaspase assay, Annexin-V and dead cell assay, and cell cycle assay. The phytochemical constituents were analyzed using GC-MS. The methanol extract of propolis exhibited cytotoxic potential against all cell lines tested. The IC50 values of the methanol extract were 47.4, 77.8, 91.2, and 145.0 ㎍/ml for HepG2, LoVo, MDAMB231, and MCF7 cell lines, respectively. The IC50 values of the F1 fraction were 31.6 (MDAMB231), 38.9 (HepG2), 36.7 (LoVo) and 75.5 (MCF7) ㎍/ml. On further purification using thin-layer chromatography, the IC50 values of the F1-3 fraction were found to be 84.31(HepG2), 79.2 (MCF7), 70.4 (LoVo), and 68.9 (MDAMB231) ㎍/ml, respectively. The anticancer potential of the F1 fraction was confirmed through the induction of apoptosis and cell cycle arrest at the G0/G1 phase. The GC-MS analysis of the F1 fraction revealed the presence of 3-methyl-4-isopropylphenol (29.44%) as a major constituent. These findings indicate the potential of propolis extract as a cancer therapy. However, further investigation is required to assess the acute and subacute toxicity of the most active fraction.

Preparation of Liquefied Cellulose and Analysis of Its Components by GC-MS Spectrometry (액화셀룰로오스의 제조 및 GC-MS에 의한 그 성분 분석)

  • 조국란;황병호;공영토;도금현
    • Journal of Korea Foresty Energy
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    • v.19 no.2
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    • pp.86-92
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    • 2000
  • The liquefactions of $\alpha$-cellulose(Sigma Chemical, C-8002, 47H0383) was prepared in the presence of phenol using sulfuric acid as a catalyst under $N_2$ gas protection at $180^{\circ}C$ for 60minutes to examine its components. The ratio of $\alpha$-cellulose to phenol was 1: 6.2(w/w), and that to sulfuric acid was 1: 0.05(g/$m\ell$). The yields of liquefaction were calculated after the liquefied mixtures were passed through 1G4 glass filter. The luquefied product of $\alpha$-cellulose was analyzed using GC-MS Spectormeter. The 12 compounds identified by GC-MS Spectrometer, of which peak area covers 54% as 2,4-dimethyl phenol, p-isopropyl phenol, 1-ethyl-3,5-dimethyl benzene, o-isopropyl phenol, (E)-2,4\` dihydroxy-stilbene, 2,2\`-methylene-bisphenol, 4,4\`-methylenebisphenol, 3-methyl-2-hydroxyphenyl-(E)-2-hydroxyl-4\`-methoxy-stilbene, 1-phyenyl-1-(4\`hydroxyphenyl)methanol phenol derivatives. From this results, the reaction pathways of the liquefaction of cellulose were proposed through electrophilic substitution reaction. Phenol as a solvent might react with the reaction intermediates as well in the cellulose liquefaction.

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