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Enzymatic Glycosylation of Fatty Acids by Methyl Glycosides (메틸글리코시드에 의한 지방산의 효소적 배당화)

  • SunWoo, Hwan;Kim, Chong-Tai;Kim, Hae-Sung
    • Journal of the Korean Applied Science and Technology
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    • v.16 no.1
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    • pp.83-94
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    • 1999
  • Glycoside fatty acid esters were synthesized by lipase-catalyzed glycosylation of fatty acids with methyl glycoside in solvent and solvent free process. Optimum condition of solvent process using 2-methyl-2-propanol were : moral ratio of methyl glycoside to fatty acid 1:3: initial concentration of methyl glycoside 50g/l:enzyme(immodilized lipase Novozym 435 from Candidia antarctica) content 1%(w/v) : desiccant content 9%(w/v); reaction temperature $60^{\circ}C$: reaction time 10hrs. The yield of 99% was obtained. Solvent-free process was carried out in total absence of solvent at $70^{\circ}C$ under reduced pressure, 5-20mmHg. To give meximum yield of 99% at the optimum condition of molar ratio of methyl glycoside to fatty acid 1:3, enzyme content 10%(w/w), and reaction time 10hrs. The glycosylation reactivity of different glycosylation agents were sequent to $Methyl-{\beta}-D-fructofuranoside$. $Methyl-{\beta}-D-glucopyranoside$. $Methyl-{\beta}-D-fructofuranosi$ de, and $Methyl-{\alpha}-D-glucopyranoside$.

Cashew Nut Oil: Extraction, Chromatographic and Rheological Characterisation.

  • Vincent Okechuwku ANIDIOBU;Chioma Oluchi ANIDIOBU
    • The Korean Journal of Food & Health Convergence
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    • v.9 no.4
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    • pp.11-18
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    • 2023
  • Oil was extracted from cashew nuts. The physicochemical parameters of the oil were determined. A chromatographic assay of the oil was carried out using Gas Chromatography-Mass Spectrometry. Seventeen compounds were detected: Phenol, Phenol 2-methyl-, Cyclohexene 4, 4-dimethyl-, m-Fluoro-2-diazoacetophenone 4-dimethyl-, Tetradecanoic acid, Phenol 4-octyl-, n-Hexadecanoic acid. Others are 9, 12-Octadecadienoic acid (Z, Z) - methyl ester, Hexadecanoic acid methyl ester, Methyl stearate, Dodecanoic acid methyl ester, 9, 12, 15-Octadecatrienoic acid methyl ester, 9, 12, 15-Octadecatrienoic acid (Z, Z, Z)-, Oleic acid, Octadecanoic acid, Tetracosanoic acid and 9-Octadecenoic acid methyl ester. Among the components are omega three and omega six essential free fatty acids. The rheological profiling and flow properties of cashew nut oil were determined using a Programmable Rheometer. Cashew nut oil exhibits slight dilatant behaviour at the low end of shear rate. The long chain and high molecular weight of its constituents controlled its rheology. Long-chained 9-Octadecenoic acid methyl ester, 9, 12-Octadecadienoic acid (Z, Z) - methyl ester, Tetracosanoic acid and methyl stearate, coupled with their high molecular weights are responsible for the shear thickening effect observed. Two models, Carreau-Yasuda and Ostwald-de Waele Power Law were employed to fit the rheological data. The Carreau-Yasuda model followed well the data.

Teratological Evaluation of Azinphos-Methyl in Rat Fetuses (Azinphos-methyl이 랫트 태아에 미치는 기형학적 연구)

  • Cho, Myung-Haing;Lee, Chang-Eop;Lee, Yong-Soon
    • Toxicological Research
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    • v.4 no.1
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    • pp.55-84
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    • 1988
  • This study was carried out to investigate the teratological potential of azinphos-methyl in the rat fetuses and to establish the nature of the effects on organogenesis and intrauterine development. The Sprague-Dawley female rats (180-210g) without previous litter were used in this study. Azinphos-methyl dosages of 0.094mg/kg, 0.4mg/kg, 1.5mg/kg were selected based on the acute intragastric $LD_{50}$ of 15mg/kg in the rat. Azinphos-methyl in water (Treatment Group), non-treatment control (Negative Control), water control (Sham Control), were administered by oral route and aqueous solution of acetyl salicylic acid (Positive Control) was administered by gavage at rate of 10 ml/kg of body weight from day 6 through 15. The results obtained were summarized as follows. 1. Decreased body weight of dams was observed in animals treated with aspirin and azinphos-methyl 1.5 mg/kg from day 7 through 14. (P<0.01) 2. There was an apparent decrement in the absolute liver weight in the azinphos-methyl 1.5 mg/kg treated group (P<0.05). However, the absolute and relative kidney weight in aspirin group (P<0.05, P<0.01) and the absolute and relative ovary weight in aspirin, azinphos-methyl treatment groups (P<0.01, P<0.05) were increased. 3. Decreased protein contents of dam's liver was observed in the aspirin and high dose azinphos-methyl treated group of animals (P<0.01). 4. The number of male-female ratio per dam increased in azinphos-methyl 1.5 mg/kg group but there was an apparent decrement in the body weight of fetuses in aspirin and high dose azinphos-methyl group (P<0.01, P<0.05). Total immature and resorbed fetuses were increased in aspirin group and the number of dead fetuses were also increased in azinphos-methyl 1.5mg/kg treated group of animals. (P<0.01, P<0.05). 5. In soft tissue defects, diaphragmatic hernia in diaphragm, anophthalmia, enlarged olfactory bulb, hydrocephalus, absence of third and lateral ventricle in skull, hydronephrosis in kidney, atrophy of left ventricle wall, enlarged apex in heart were observed. Especially, defects of diaphragm, heart and eye ball showed peak incidences in the high dose azinphosmethyl and aspirin group. (P<0.01). 6. Variations in the ossification patterns of skull, sternebrae, tail, forelimbs and hindlimbs showed peak incidences in the aspirin and high dose azinphos-methyl group. (P<0.01). 7. In the developmental indices of offspring, the mortality of aspirin and azinphos-methyl 1.5mg/kg treated group was higher than that of negative control. And, there was an apparent decrement in the body weight of fetuses (P<0.01) and considerable differences were obtained in pivoting, development of fur, auditory function, vision, quadrupled muscle development and testes descent in aspirin and azinphos-methyl 1.5mg/kg group. (P<0.01).

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Steric Hindrance in the Free Radical Polymerization of Aryloxyethyl Vinyl Ethers Containing Electron-Deficient Olefin Groups$^{\dag}$

  • Lee, Ju Yeon;Jin, Mi Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.21 no.6
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    • pp.613-617
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    • 2000
  • p-(2-Vinyloxyethoxy)benzylidenemalononitrile (4a), methyl p-(2-vinyloxyethoxy)benzylidenecyanoacetate (4b), 3,5-dimethoxy-4-(2'-vinyloxyethoxy)benzylidenemalononitrile (5a), methyl 3,5-dimethoxy-4-(2'-vinyloxy-ethoxy) benzylidenecyanoacetate (5 b), o-(2 -vinyloxyethoxy)benzylidenemalononitrile (6a), methyl o-(2-viny-Ioxyethoxy) benzylidenecyanoacetate (6b), 1,3-di-(2',2'-dicyanovinyl)-5-methyl-2-(2'-vinyloxyetioxy)benzene (7a), l,3-di-(2'-carbomethoxy-2'-cyanovinyl)-5-methyl-2-(2'-vinyloxyethoxy)benzene (7b), 2,3,4-tri-(2'-viny-Ioxyethoxy) benzylidenemalononitrile (8a), methyl 2,3,4-tri-(2'-vinyloxyethoxy)benzylidenecyanoacetate (8b), 2,4,6-tri-(2'-vinyloxyethoxy)benzylidenemalononitrile (9a), and methyl 2,4,6-tri-(2'-vinyloxyethoxy)benzyl-idenecyanoacetate(9b) were prepared by the condensation of the corresponding benzaldehyde 1-3 with malononitrile or methyl cyanoacetate, respectively. Vinyl ether monomers 4, 6, and 8 polymerized readily with radical initiators to yield crosslinked polymers 10, 12, and 14. However, compounds 5, 7, and 9 were inert to radical initiators due to the steric hindrance. The resulting polymers 10, 12, and 14 were not soluble in common solvents showing a thermal stability up to $300^{\circ}C$.

Synthesis of Methyl 2, 6-Dimethyl-5-(1', 2'-Dioxo-2'-Ethoxyethyl)-4-(3'-Nitrophenyl)-1, 4 Dihydropyridine -3-Carboxylate

  • Suh, Jung-Jin;Hong, You-Hwa
    • Archives of Pharmacal Research
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    • v.13 no.3
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    • pp.257-260
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    • 1990
  • Hantzch's type reaction of methyl acetopyruvate (2a), methyl 3-aminocrotonate (3) and 3-nitrobenzaldehyde (4) led to dimethyl 3-acetyl-6-methyl-4-(3'-nitrophenyl)-2, 5-dicarboxylate (5a) and methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'-methoxyethyl)-4-(3' nitrophenyl)- 2, 5-dicarboxylate (5a) and methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'methoxyethyl_4-(3' nitrophenyl)1, 4-dihydropyridine-3-carboxylate (6a) in 26.7 and 9.2% yield, respectively. On the other hand, methyl 2, 60dimethyl-4-(3'-nitrophenyl)-1, 4-dihydropyridine 3-carboxylate (9) was acylated by ethyl oxaly chloride to give methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'-ethoxyethyl)-4-(3'-nitrophenyl)-a, 4-dihydropyridine-3-carboxylate (6b) in 76.8% yield.

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Resistance of Dendrophoma obscurans to thiophanate-methyl and iprodione (딸기 겹무늬병균의 Thiophanate-methyl 및 Iprodione 제에 대한 저항성)

  • Moon Byung Ju;Cho Chong Taik
    • Korean journal of applied entomology
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    • v.23 no.2 s.59
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    • pp.89-95
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    • 1984
  • Sixty isolates of Dendrophoma obscurans isolated from 19 important strawberry growing areas of Korea were tested in vitro for resistance to thiophanate-methyl and iprodione. Naturally-occurring thiophanate-methyl-resistant isolates were about 43 percents of isolates tested, whereas iprodione-resistant isolates were 10 percents. All these resistant isolates except SU 1 and SU 2, which were highly resistant to thiophanate-methyl, showed a week level of resistance. Iprodione-resistant isolates were readily obtained in vitro, when mycelial disk of the fungus was incubated on PDA media containing iprodione at the concentrations of $1{\mu}g/ml\;and\;10{\mu}g/ml$, but no thiophanate-methyl-resistant isolate from the mycelia with or without UV irradiation. All these artificially-obtained iprodione-resistant isolates were showed a high degree of resistance. On the strawberry leaves, thiophanate-methyl and iprodione were no longer effective to all resistant isolates at the recommended concentration, and the protective value to highly resistant isolates was much less than that of weakly resistant isolates. Isolates resistant to thiophanate-methyl were also resistant to benomyl but iprodione-resistant isolates did not show cross-resistance to thiophanate-methyl, benomyl, captan and zineb. Captan controlled both thiophanate methyl-resistant and iprodione-resistant isolates as effectively as sensitive isolates.

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Synthesis and Characterization of Poly(Urethane-Methyl methacrylate) Hybrid Emulsion as a Plastic Coating Resin (플라스틱 코팅용 Poly(Urethane-MMA) 혼성 에멀젼 합성 및 특성 연구)

  • Yeom, Ji-Yoon;Baek, Kyung-Hyun;Lee, Jun-Young;Yi, Gyoung-Bae;Yoo, Byung-Won;Kim, Jung-Hyun
    • Journal of Adhesion and Interface
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    • v.8 no.1
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    • pp.8-14
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    • 2007
  • Poly(urethane-methyl methacrylate) hybrid emulsions can be controlled with their thermal, mechanical and anti-chemical properties as plastic coating materials. In this study, water dispersed poly(urethane-methyl methacrylate) hybrid emulsions were prepared by prepolymer synthesis and soap free emulsion polymerization. For imparting hydrophilicity on polyurethane prepolymer, 2,2-bis (hydroxymethyl) propionic acid was added to the polyurethane prepolymer with methyl methacrylate monomer and was neutralizated by triethylamine (TEA). After neutralization, the prepolymer mixture was dispersed in the water phase with stable droplets. The synthesis was carried out with chain extension from the ethylene diamine and initiation of methyl methacrylate by soap free emulsion polymerization. Stable poly(urethane-methyl methacrylate) hybrid emulsion was successfully obtained with different synthetic conditions and acrylic monomer contents. Poly(urethane-methyl methacrylate) hybrid emulsion were characterized and compared with tensile strength, viscosity, and adhesion properties.

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Studies on the Synthesis of Nonionic Surfactants (III). Kinetics of the Synthesis of Sucrose Esters (비이온성 계면활성제의 합성에 관한 연구 (제3보). 슈크로오스에스테르의 합성에 관한 동력학적 고찰)

  • Ki Dae Nam;Joo Hwan Sohn
    • Journal of the Korean Chemical Society
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    • v.25 no.4
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    • pp.283-290
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    • 1981
  • The reaction rates for the transesterification reaction were measured on the excess sucrose with the five fatty acid methyl ester systems such as methyl laurate, methyl myristate, methyl palmitate, methyl stearate and methyl oleate at temperature range of $50^{\circ}C$ to $90^{\circ}C$ in N,N-dimethylformamide solvent and potassium carbonate as a catalyst. Their activation parameters as well as rate constants were calculated from these measurements. And these reactions were found to be pseudo-first order and depended mainly on the structural changes in fatty acid residue of methyl esters. Also their reactions were found to be of enthalpy-controlled, which were disfavored in the order of methyl laurate, methyl myristate, methyl palmitate, methyl oleate and methyl stearate. Correspondingly their activation energies were 9.3, 9.9, 10.3, 10.9 and 11.1 kcal/mole, respectively.

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1,2,4-Triazine III : Synthesis of 1-Methyl-1,2,4-triazinium Iodides and Their Ring Contraction Reaction to 1-Methyl-1,2,4-triazoles (1,2,4-Triazine III : 1,2,4-Triazine 유도체의 Methiodide 염 합성과 이들 염의 고리 축소화반응에 의한 1,2,4-Triazole 유도체 합성)

  • Jae Keun Lee;Ryu Hyang Sun;W. W. Paudler
    • Journal of the Korean Chemical Society
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    • v.33 no.4
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    • pp.419-425
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    • 1989
  • Various 1-methyl-1,2,4-triazinium iodides were easily synthesized by the reaction of various 1,2,4-triazines and methyl iodide in acetone. When methyl iodide salts of 1,2,4-triazine derivatives were treated with $K_3Fd(CN)_6$ in 10% NaOH solution, 1-methyl-1,2,4-triazole derivatives as the main products were obtained by ring contraction. In addition to 1-methyl-1,2,4-triazole derivatives, 1,6-dihydro-6-oxo-1,2,4-triazine derivatives as the minor products were also obtained when there were no substitutents in $C_6$-position of 1,2,4-triazines. The formation of pseudo base by $OH^-$ and then oxidation to either 1,6-dihydro-6-oxo-1,2,4-triazines or 1-methyl-1,2,4-triazoles were suggested as the mechanism of the ring contraction. This mechanism also verified that the position of quaternization was neither $N_2$ nor $N_4$ but 1-nitrogen of 1,2,4-triazine.

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Immunotoxicity of Organophosphorous Pesticides, Pirimiphos-methyl and Methidathion in Balb/c Mice (Balb/c 마우스에서 유기인계 농약인 Pirimiphos-methyl 및 Methidathion의 면역독성)

  • Eam Juno H.;Chung Seung-Tae;Park Jae Hyun;Kil Jung Hyun;Lee Jong Kwon;Oh Hye Young;Kim Hyung Soo
    • Toxicological Research
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    • v.20 no.4
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    • pp.329-337
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    • 2004
  • Primiphos-methyl and methidathion as organophosphorus (OP) pesticides were tested for their immunotoxic effects on Balb/c mice. Three dose levels of primiphos-methyl (10, 60, or 120 mg/kg/day) and methidathion (0.5, 2.5 or 5.0 mg/kg/day) were administered orally in the mice for 4 weeks. After, changes in body weight gain, relative weight of spleen and thymus, viable splenic cell numbers, surface marker on immune cell, and proliferation activity were investigated. Results showed that neither Pirimiphos-methyl nor methidathion dosages changed significantly body weight, relative thymus and spleen weight, and thymus and spleen cellularities of the mice, but high dose treatment (120 mg/kg) of pirimiphos-methyl significantly decreased relative spleen weight and spleen cellularity of the mice. No alterations were observed in changes of LPS-proliferation response of splenocytes by exposure to any dose of pirimiphos-methyl and methidathion. However, pirimiphos-methyl dosages reduced ConA-proliferation response of splenocytes and both methidathion and pirimiphos-methyl decreased the ability of antibody production to SRBC. The results indicate that 28 days exposure to the high dose of pirimiphos-methyl suppress the function of splenic T and B cell function, and methidathion reduce the immune responsibility of B cell in mice without the changes in lymphoid organ weight or viability of splenocytes. Pirimiphos-methyl is more immunotoxic than methidathion although this has higher general toxicity than that.