• Bulletin of the Korean Chemical Society
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• 제26권12호
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• pp.2007-2016
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• 2005

An artificial neural network (ANN) is successfully presented for prediction acidity constant (pKa) of various benzoic acids and phenols with diverse chemical structures using a nonlinear quantitative structure-property relationship. A three-layered feed forward ANN with back-propagation of error was generated using six molecular descriptors appearing in the multi-parameter linear regression (MLR) model. The polarizability term $(\pi_1)$, most positive charge of acidic hydrogen atom $(q^+)$, molecular weight (MW), most negative charge of the acidic oxygen atom $(q^-)$, the hydrogen-bond accepting ability $(\epsilon_B)$ and partial charge weighted topological electronic (PCWTE) descriptors are inputs and its output is pKa. It was found that properly selected and trained neural network with 205 compounds could fairly represent dependence of the acidity constant on molecular descriptors. For evaluation of the predictive power of the generated ANN, an optimized network was applied for prediction pKa values of 37 compounds in the prediction set, which were not used in the optimization procedure. Squared correlation coefficient $(R^2)$ and root mean square error (RMSE) of 0.9147 and 0.9388 for prediction set by the MLR model should be compared with the values of 0.9939 and 0.2575 by the ANN model. These improvements are due to the fact that acidity constant of benzoic acids and phenols in water shows nonlinear correlations with the molecular descriptors.

• Biotechnology and Bioprocess Engineering:BBE
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• 제11권6호
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• pp.477-483
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• 2006

Ionic liquids in the form of organic salts are being widely used as new solvent media. In this paper three positional isomers, o-amino benzoic acid, m-amino benzoic acid, and p-amino benzoic acids were separated with four different ionic liquids as mobile phase additives using high performance liquid chromatography (HPLC). The following ionic liquids were used: 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIm][$BF_{4}$]), 1-ethyl-3-methylimidazolium tetrafluoroborate ([EMIm][$BF_{4}$]), 1-ethyl-3-methylimidazolium methylsulfate ([EMIm][MS]), and 1-octyl-3-methylimidazolium methylsulfate ([OMIm][MS]). The effects of the alkyl group length on the imidazolium ring and its counterion, and the concentrations of the ionic liquids on the retention factors and resolutions of amino benzoic acid isomers were tested. The results of the separations with ionic liquids as the eluents were better than those without ionic liquids. Excellent separations of the three isomers were achieved using 2.0-8.0 mM/L [OMIm][MS] and 1.0-8.0 mM/L [EMIm][MS] as the eluent modifiers.

• Food Science and Biotechnology
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• 제14권3호
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• pp.371-374
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• 2005

The compositions and antioxidant activities of tree and hydrolyzed phenolic acids, which are aglycones of esterified phenolic acids, in wild ginseng leaves were investigated. The contents of tree and hydrolyzed phenolic acids in the wild ginseng leaves were $422.4\;{\pm}\;3.5$ and $319.6\;{\pm}\;5.7\;mg/100\;g$, respectively, as gallic acid equivalents. Free phenolic acids were composed of 55.3% benzoic acid derivatives and 44.6% phenylpropanoids. The major constituents of free phenolic acids in the ginseng leaves were syringic (139.4 mg/l00 g) and sinapic (131.2 mg/100 g) acids. On the other hand, hydrolyzed phenolic acids in the ginseng leaves were mainly composed of caffeic (59.4 mg/100 g), ferulic (49.5 mg/100 g), and p-coumaric (33.8 mg/100g) acids. Phenylpropanoid content was higher (82.7%) than benzoic acid derivatives (17.3%). $IC_{50}$ values of DPPH radical scavenging activity were $10.2\;{\mu}g/mL$ for tree phenolic acids and 8.0 mg/mL for hydrolyzed phenolic acids, as gallic acid equivalents. Hydrolyzed phenolic acids also exhibited higher hydroxyl and superoxide radical scavenging activities than free phenolic acids did. These results indicated that the antioxidant activities of the wild ginseng leaves were correlated more closely with phenylpropanoid contents than with total amount of phenolics.

• 약학회지
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• 제38권3호
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• pp.230-237
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• 1994

The structure-activity relationships of (E)-chalcone-4-carboxylic acids, flavone-4'-carboxylic acids, two types of aromatic amides, terephthalic monoanilides, and (arylcarboxamido)benzoic acids, which were made by Shudo group, are discussed by conformation analysis(AM1) of retinoic acid and those compounds. Conformer of each compound is superimposed on the conformationally restricted compound, 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphto[ 2,3-b]pyran-2-yl) benzoic acid(Fv80), possessing the strongest differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The results indicated that the lengths between the carboxylic carbon and the two 6, 9 carbons binding to dimethyl, 1.20 nm and 1.09 nm, as well as the planarity of molecule are very important factors for the activity, especially 1.20 nm. In the case of the recently synthesized azulenic retinoic acids by Sato, et al. in 1993, the distance probably is also important, resulted from superimposing them on a Ch55 conformer and Fv80. The distance 1.0 nm is also important in Ch55. Several conformers of all-trans retinoic acid (RA) are well superimposed on the almost non-flexible Fv80, RA, 9-cis RA, and, specifically s-10,12 cis RA. And a simple hexangular model of RA is suggested to draw RA conformers easily without computer drawing model or molecular model.

• 한국응용과학기술학회지
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• 제11권1호
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• pp.53-60
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• 1994

The Synthesis of azobenzene containing long chain fatty acid and poly vinyl alcohol by esterification reaction($C_{n}-Azo-PVA$) was optimized, starting from P-(P'-hydroxy phenyl azo)-benzoic acid and the product of reaction containing azobenzene chromophores was investigated by ultraviolet spectrophotometery in toluene solvent at room temperature. In addition, UV absorption spectra of Langmmuir Blodggett (LB) film deposited on quartz plate have been measured and the structure of these compounds were ascertained by means of Ultraviolet and FT-IR. Recrystallization of reaction product in the solvent results the experimental yield obtained about 22.27% P-(P'-octadecyloxy phenyl azo)-benzoic acid-poly vinyl alcohol. Long chain azobenzene derivative-poly vinyl alcohols are induced phtoisomerization by u, v, and visible light irradiation. The LB film of azobenzene containing long chain fatty acids($C_{18}-Azo-PVA$) are possible of being applied to functional molecular devices such as photomemory and light switching.

• 대한화학회지
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• 제18권5호
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• pp.358-362
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• 1974

벤조산과 그 유도체들에 대한 음이온 교환분리를 여러 농도의 염화니켈-메탄올 용매 내에서 연구하였다. Amberlite CG-400, $Cl^-$ form에 대한 유기산들의 부피분배계수를 측정하고 이 분배계수로부터 제시된 적절한 농도의 $NiCl_2-MeOH$ 용액을 용리액으로 사용하여 몇 개의 혼합유기산을 정량적으로 분리하였다. 모든 유기산들의 농도는 자외선 분광광도계를 사용하여 정량하였다.

• 대한화학회지
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• 제55권3호
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• pp.392-399
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• 2011

벤조산 유도체($NH_2$, OH, H, F, Cl, CN, NO, $NO_2$) 의 두 형태를 6-311++G(d,p) 바탕 집합을 이용하여 MP2, DFT 및 HF 수준으로 연구하였으며, cis이성 질체가 더 안정하였다. 벤조산의 수소 결합 형성은 안정화 에너지를 이용하여 추산하였으며, 이합체에 대한 수소결합 에너지 계산치는 고리에서 협동 상호작용이 일어남을 보여주었다. 페닐 고리로 전자를 밀어내는 그룹(ERG)은 더 안정한 수소 결합이 형성하였다. 이합체에서 O-H 결합의 적색이동은 -565.3에서 $-589.3\;cm^{-1}$ 범위였으며, 상호 작용의 특성은 NBO 분석을 이용하여 연구하였다.

• 대한화학회지
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• 제35권3호
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• pp.196-203
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• 1991

25$^{\circ}$C 때 벤조산과 메타 및 파라위치에 할로겐(F, Cl, Br)이 치환된 $pK_a$값을 메탄올-물 혼합용매(0∼80% 메탄올) 중에서 Fuoss-Kraus 식에 근거한 전도도법과 Gelb의 전도도법을 이용하여 결정하였다. 할로겐 치환기에 따른 벤조산의 $pK_a$ 변화를 전자받게 유도효과와 전자주게 공명효과로 복합시킨 치환기 상수(${\sigma}_1$ 및 ${\sigma}_R$)로써 논의하였다. ${\sigma}_1$가 $D^{-1}$에 대하여 양(+)의 기울기를 갖는 직선성을 보인 반면 ${\sigma}_R$은 $D^{-1}$에 대하여 음(-)의 기울기를 갖는 직선성을 보이고 있는데, 이를 field effect의 유전상수 의존성과 할로겐 치환기의 ${\pi}$-고립쌍 전자와 이온화 중심간의 through-space ${\pi}$-상호작용으로 해석하였다.

• KSBB Journal
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• 제7권2호
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• pp.118-125
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• 1992

1.에멀젼형 화장품시료의 오염정도는 P. aeruginosa의 증식을 촉진하는 fatty acids, waxs, oils, steroids 등의 유기물에 의존하였다. 2. 오염의 결과, 물성의 변화로서 화장품시료의 pH가 40일 경과시 7.6에서 6.0으로 변화되었다. P. aeruginosa의 영양원으로서는 상대적으로 낮은 굴절률을 갖는 물질들이 소모되어 화장품시료(물:오일=70:30)의 굴절률이 1.4430에서 1.4530으로 변화 되었다. 3. 오염이 진행되는 동안 화장품시료의 相의 안정서이 파괴되었으며, 약간의 변색, 변취와 함께 creaming 및 응집현상이 나타났다. 4. P. aeruginosa의 최적증식조건인 pH7.0, 온도$20^{\circ}C$에서, 물과 오일의 부피비에 의한 균증식은 70:30, 80:20, 30:70, 90:10, 50:50의 순서로 되었다. 5. 방부살균제를 첨가하여 challenge test를 한 결과, P. aeruginosa의 증식이 억제되었으며 40일 경과시 균수는 방부살균제를 첨가하지 않은 경우 $10^8$개/ml에서 p-hydroxy benzoic acid propyl ester + phosphoric acid buffer solution첨가로 $5{\times}10^3$ 개/ml로 감소되었다. 6. 시험균주인 P. aeruginosa에 대한 항균력은 p-hydroxy benzoic acid propyl ester + phosphoric acid buffer solution>p-hydroxy benzoic acid buthyl ester + acetic acid buffer solution>p-hydroxy benzoic acid methyl ester + phosphoric acid buffer solution>p-hydroxy benzoic acid methyl ester + p-hydroxy benzoic acid propyl ester>p-hydroxy benzoic acid buthyl ester + potassium chloride sodium hydroxide buffer solution>p-hydroxy benzoic acid buthyl ester + p-hydroxy benzoic acid propyl ester>p-hydroxy benzoic acid methyl ester + acetic acid vbuffer solution>acetic acid buffer solution _ potassium chloride sodium hydroxide buffer solution의 순으로 우수하였으며 pH, 농도, 균수등은 양호한 수준을 유지하였다.

• 한국축산식품학회지
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• 제36권4호
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• pp.531-537
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• 2016

In milk and milk products, a number of organic acids naturally occur. We investigated the contents of some naturally occurred food preservatives (sorbic acid, benzoic acid, propionic acid, nitrite, and nitrate) contained in domestic and imported cheeses to establish the standard for the allowable range of food preservatives content in cheese. 8 kinds of domestic precheeses (n=104), 16 kinds of domestic cured cheeses (n=204) and 40 kinds of imported cheeses (n=74) were collected. Each domestic cheese was aged for a suitable number of months and stored for 2 mon at 5℃ and 10℃. No preservatives were detected in domestic soft and fresh cheeses, except cream cheese. In case of semi-hard cheeses, 2-5 mg/kg of benzoic acid was detected after 1-2 mon of aging. In imported cheeses, only benzoic acid and propionic acid were detected. The average benzoic acid and propionic acid contents in semi-hard cheese were 8.73 mg/kg and 18.78 mg/kg, respectively. Specifically, 1.16 mg/kg and 6.80 mg/kg of benzoic acid and propionic acid, respectively, were contained in soft cheese, 3.27 mg/kg and 2.84 mg/kg, respectively, in fresh cheese, 1.87 mg/kg and not detected, respectively, in hard cheese, and 2.07 mg/kg and 182.26 mg/kg, respectively, in blended processed cheese.