• Title/Summary/Keyword: Phenylacetic acid

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A Mechanistic Study for Aminolysis of p-Nitrophenyl Phenylacetate

  • 엄익환;Yeom, E. Suk;권혜진;권동숙
    • Bulletin of the Korean Chemical Society
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    • v.18 no.8
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    • pp.865-868
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    • 1997
  • Second-order rate constants have been measured spectrophotometrically for the reactions of p-nitrophenyl phenylacetate (1) and benzoate (2) with a series of alicyclic amines in H2O containing 20 mole % DMSO at 25.0 ℃. 1 appears to be more reactive than 2 toward all the amines studied, although phenylacetic acid is a weaker acid than benzoic acid. The higher reactivity of 1 can be attributed to resonance and/or steric effect, since the ground state of 2 can be stabilized by resonance and 1 would experience less steric hindrance due to the presence of CH2 group between phenyl and C=O group. The reactivity of the amines increases with increasing their basicity. The Bronsted-type plots for aminolysis of 1 and 2 show good linearity with βnuc values of 0.81 and 0.85, respectively, indicating that the TS structures of the aminolyses of 1 and 2 are similar. Besides, the linear Bronsted plots obtained in the present system clearly suggest that there is no mechanism change for the given series of the amines and the reactions of 1 and 2 proceed in a same mechanism.

Base Catalysed Hydrolysis of Aryl Phenylacetates (Aryl Phenylacetate류의 염기촉매 가수분해 반응)

  • Duk-Young Cheong;Soo-Dong Yoh;Jae-Hwan Choi;Kwang-Taik Shim
    • Journal of the Korean Chemical Society
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    • v.36 no.3
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    • pp.446-452
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    • 1992
  • The rates of hydrolysis of aryl phenylacetates have been measured in the presence of piperidine in 80% acetonitrile-20% water(v/v). For the electron withdrawing substituents of leaving group, the hydrolysis is catalyzed by a general base and the Hammett $\rho_{LG}$ and Bronsted value $\beta$ are 5.28 and -2.72 at $30^{\circ}C$, respectively. These high senstivities of Hammett and Bronsted values are $E1_{C}B$ mechanism. But in the electron donating ones, the hydrolysis is catalyzed by a specific base and $B_{AC}2 mechanism is predominated. $pK_{SH}'s of phenylacetic acid ester and rate constants of hydrolysis $k_1$, $k_{-1)$, $k_2$ were calculated.

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Differentiation of Roots of Glycyrrhiza Species by 1H Nuclear Magnetic Resonance Spectroscopy and Multivariate Statistical Analysis

  • Yang, Seung-Ok;Hyun, Sun-Hee;Kim, So-Hyun;Kim, Hee-Su;Lee, Jae-Hwi;Whang, Wan-Kyun;Lee, Min-Won;Choi, Hyung-Kyoon
    • Bulletin of the Korean Chemical Society
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    • v.31 no.4
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    • pp.825-828
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    • 2010
  • To classify Glycyrrhiza species, samples of different species were analyzed by $^1H$ NMR-based metabolomics technique. Partial least squares discriminant analysis (PLS-DA) was used as the multivariate statistical analysis of the 1H NMR data sets. There was a clear separation between various Glycyrrhiza species in the PLS-DA derived score plots. The PLS-DA model was validated, and the key metabolites contributing to the separation in the score plots of various Glycyrrhiza species were lactic acid, alanine, arginine, proline, malic acid, asparagine, choline, glycine, glucose, sucrose, 4-hydroxy-phenylacetic acid, and formic acid. The compounds present at relatively high levels were glucose, and 4-hydroxyphenylacetic acid in G. glabra; lactic acid, alanine, and proline in G. inflata; and arginine, malic acid, and sucrose in G. uralensis. This is the first study to perform the global metabolomic profiling and differentiation of Glycyrrhiza species using $^1H$ NMR and multivariate statistical analysis.

Competitive Effects of Allelochemics on the Monoculture and Corss-cropping Culture System of Plants (작물(作物)의 단일(單一) 및 교호(交互) 재배시(栽培時) 알레로파지 특성(特性)에 관(關)한 연구(硏究))

  • Suh, Jang-Sun;Lee, Sang-Kyu
    • Korean Journal of Soil Science and Fertilizer
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    • v.26 no.4
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    • pp.259-264
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    • 1993
  • Allelopathic chemicals exudated from plants stimulate or inhibit crops directly or indirectly. To prove the effects of allelochemics, we isolated and identified the compounds by bioassays on the monoculture and crosscropping cultre systems. p-Coumaric acid were exudated on all of the test crops such as tomato, red pepper, lettuce, chinese cabbage and sesame, but pyrogallol and phenylacetic acid on tomato. hydroquinone on red pepper and egg plant, pyrogallol on lettuce, and vanillic acid on chinese cabbage. The highest total concentration of allelochemics was $5,883{\mu}g$ on tomato, lowest was $220{\mu}g/g$ dry plant weight on sesame. On the cross-cropping culture of tomato-egg plant, tomato-red pepper, chinese cabbage-egg plant, chinese cabbage-red pepper and chinese cabbage-sasame, the plant height, aerial dry weight and total dry weight of the tomato and the chinese cabbage were inereased contrast with monoculture, but decreased greatly on red pepper and sesame. Growth rate of both crops on the cross-cropping culture of tomato-chinese cabbage declined, while that of chinese cabbage was increased but lettuce decreased on the chinese cabbage-lettuce cross-cropping culture contrast with monoculture.

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Synthesis of Higenamine, A Cardiotonic Principle of Aconite Root

  • Chang, Ki-Churl;Choi, Sook-Yun;Lim, Jung-Kyoo;Park, Chan-Woong
    • Archives of Pharmacal Research
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    • v.7 no.2
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    • pp.133-136
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    • 1984
  • Higenamine (I), cardiotonic principle of Aconite root, was synthesized from 4-methoxy-phenylacetic acid (II) and .betha.-(3, 4-dimethoxyphenyl)-ethylamine (IV). Condensation of IV with 4-mehoxyphenylacetyl chloride (III) was followed by cyclodehydration yielding 1-(4'-methoxybenzyl)-6, 7- dimethoxy-3, 4-dihydroisoquinoline (VI). Reduction of VI to 1, 2, 3, 4-tetrahydroisoquinoline (VII) and subsequent demethylation provided desired product higenamine, 1-(4'-hydroxybenzyl)-6, 7- dihydroxy-1, 2, 3, 4, -tetrahydroisoquinoline.

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Changes of the Extracellular Concentrations of Striatal Dopamine and Its Metabolites by MK-801 in Morphine-Dependent Rats (MK-801 투여에 의한 몰핀의존성랫드 뇌선초체중 도파민신경절달물질의 변화)

  • 이선희;신대섭;유영아;류승렬;김대병
    • Biomolecules & Therapeutics
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    • v.6 no.1
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    • pp.25-30
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    • 1998
  • The roles of dopamine(DA) and N-methyl-D-aspartate(NMDA) system in the development and expression of morphine dependence were investigated by monitoring the concentrations of extracellular DA and its metabolites by in vivo microdialysis and simultaneous observation of behavioral changes in morphine dependent rats. Extracellular DA level in caudate putamen of morphine-dependent rat was decreased and the concentrations of its metabolites, dihydroxy phenylacetic acid(DOPAC) and homovanillic acid(HVA), were increased during naloxone-precipitated withdrawal. DA contents were recovered to normal levels by pretreatment of MK-801, a noncompetitive NMDA receptor antagonist, which may explain the mechanism of diminishing effect of MK-801 on withdrawal symptoms in morphine-dependent rats. MK-801(0.3 mg/tg, i.p.) induced the untoward hamful neurological signs such as ataxia and severe rotations, which may be produced by hyperactivation of dopaminergic system. These results suggest that MK-801 may inhibit the expression of mophine dependence by altering the dopamine release.

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Synthesis of N-Aryl Phenylglycine Ο-Alkyl Esters and Its Substitution of Ester Moiety (N-Aryl Phenylglycine Ο-Alkyl Esters의 간편한 합성 및 에스테르 치환반응)

  • 박명숙;박해선
    • YAKHAK HOEJI
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    • v.47 no.5
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    • pp.276-282
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    • 2003
  • For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through esterification, bromination, C-N bond formation from commercially available phenylacetic acids. An efficient and practical reaction condition for esters 2a∼c was that the starting materials 1a∼c were refluxed in absolute methanol for 3 hours with catalytic concentrated hydrosulfuric acid. In addition, bromines 3a∼c were formated for 3h in dichloromethane at rt with N-bromosuccinimide. Bromines 3a∼c were also converted to 4a∼i through substitution of arylamines during refluxing for 24 hours in ethanol with triethylamine. Interestingly, ethyl esters 5a∼c were formed via transesterification reaction when the p-sulfamylanilino group was used as a nucleophile in ethanol solvent.

Studies on the Separation and Identification of Acids in Izmir Tobacco Leaves (Izmir 잎담배 중 Acids 성분의 분리 및 확인에 관한 연구)

  • Lee, Un-Chul;Jang, Gi-Chul;Kim, Yong-Ok
    • Journal of the Korean Society of Tobacco Science
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    • v.16 no.2
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    • pp.172-180
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    • 1994
  • This study was carried out to separate and identify the acidic compounds in tobacco leaves. Izmir tobacco leaves was extracted with isopropyl ether and the extract was concentrated. The concentrate was extracted with 6% NaHCO3 aqueous solution. The aqueous extract was acidified with sulfuric acid, and extracted with diethyl ether. The acidic material was fractionated on silicic acid column using a benzene-methanol mixture with a stepwise increasing methanol concentration. The resulting fractions were esterified with diazomethane, and then identified by GC, GC/MS using SPB -5 fused silica capillary column. Most of acidic compounds in Izmir tobacco leaves were elected from fraction B which was benzene-methanol(98 : 2) mixture on silicic acid column chromatography. The identified acidic compounds of Izmir tobacco leaves were 18 saturated acids, 8 unsaturated acids, 5 dicarboxylic acids, 13 aromatic acids and 7 terpenoid acids. The major acidic compounds of lzmir tobacco leaves were 2- methylbutanoic, 3-methyl butanoic, 3- methylpentanoic, hexanoic, nonanedioic, phenylacetic, benzoic, 4- methoxybenzoic, 3, 5- dimethoxybenzoic, methoxycinnamic and 3, 4- dimethoxycinnamic acid. Key Words : Izmir tobacco, Acidic compounds, GC/MS.

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Studies on the Penicillin Acylase Production of Genus Escherichia (Escherichia속 세균의 Penicillin Acylase 생산에 관한 연구)

  • Kang, Hyo-Won;Lee, Ju-Kyung;Bae, Moo
    • Microbiology and Biotechnology Letters
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    • v.8 no.1
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    • pp.33-39
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    • 1980
  • In order to invertigate penicillin acylase produced by a strain of Genus Escherichia, 47 strains of Genus Escherichia were isolated and examined to the extend of the inactivation of penicillins and the ability of 6-amino penicillanic acid (6-APA) production. Among them, 12 strains were found to produce penicillin acylase and to form 6-APA. The strain No. 11 of the isolates was selected to be the most excellent one producing the acylase. Optimum culture conditions for the production of the acylase of the strain were found as follows : pH at 7.6~8.0, time on 18 hrs, temperature at 34 to 38$^{\circ}C$. And effective levels of the medium were found to be contained 0.3% phenylacetic acid, 1.0% yeast extract, 1.0% peptone and 0.3% L-glutamate. And, the production of the acylase by the isolate was strongly inhibited by 1% glycerol and the growth was remarkably retarded by the addition of 1.0% n-butylacetate. The acylase was extracted from the isolate and the crude enzyme of the acylase was prepared and the characteristies of the enzyme were primary examined in optimum pH, temperature, stabilities and reaction time.

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Callus and Embryo Formation from Microspore Culture of Peony(Paeonia lactiflora Pall.) (작약(芍藥)의 화분소포자(花粉小胞子)로부터 캘러스와 배(胚) 형성(形成))

  • Sohn, Jae Keun;Kim, Kyung Min;Kwon, Yong Sham
    • Current Research on Agriculture and Life Sciences
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    • v.12
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    • pp.51-55
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    • 1994
  • Pollen microspores isolated from peony anthers were cultured by agarose embedding method in the MS medium with 2,4-D(1mg/l) or phenylacetic acid(1, 10, 100mg/l), and without plant hormone. It was observed that pollen microspores cultured on hormone-free medium were directly developed into embryos. Callus formation was enhanced from microspores which were cultured on medium supplemented with 1mg/l PAA. Embryos were also formed from the calli transferred into the hormone-free medium.

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