• Title/Summary/Keyword: $C_9$-aldehyde

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Quantitative Analysis of t-Cinnamaldehyde of Cinnamomum cassia by $^1H-NMR$ Spectrometry ($^1H-NMR$을 이용한 계피의 t-cinnamaldehyde 정량분석)

  • Song, Myoung-Chong;Yoo, Jong-Su;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.48 no.3
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    • pp.267-272
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    • 2005
  • trans-Cinnamaldehyde, a major component of Cinnamomum cassia, was quantitatively analyzed using the $^1H-NMR$ spectrometry. Applicability of this method was confirmed through observing the variation of chemical shift in the $^1H-NMR$ spectrum of t-cinnamaldehyde and the integration value according to various sample concentrations or running temperatures. When the $^1H-NMR$ spectrometry was run for t-cinnamaldehyde (7.1429 mg/ml) at 19, 25, 30, 40 and $50^{\circ}C$, the chemical shifts of the doublet methine signal due to an aldehyde group were observed at 9.7202, 9.7184, 9.7169, 9.7142 and 9.7124 ppm, respectively, to imply that the running temperature had no significant variation in the chemical shift of the signal. The integration values of the signal were $1.37\;(19^{\circ}C),\;1.37\;(25^{\circ}C),\;1.37\;(30^{\circ}C),\;1.37(40^{\circ}C)$ and $1.37(50^{\circ}C)$, respectively, to also indicate running temperature gave no effect on the integration value. When the sample solutions with various concentrations such as 0.4464, 0.8929, 1.7857, 3.5714, 7.1429 and 14.286 mg/ml were respectively measured for the $^1H-NMR$ at $25^{\circ}C$, the chemical shifts of the aldehyde group were observed at 9.7206, 9.7201, 9.7196, 9.7192, 9.7185 and 9.7174 ppm. Even though the signal was slightly shifted to the high field in proportion to the increase of sample concentration, the alteration was not significant enough to applicate this method. The calibration curve for integration values of the doublet methine signal due to the aldehyde group vs the sample concentration was linear and showed very high regression rate ($r^2=1.0000$). Meantime, the $^1H-NMR$ spectra (7.1429 mg/ml $CDCl_3,\;25^{\circ}C$) of t-cinnamaldehyde and t-2-methoxycinnamaldehyde, another constituent of Cinnamomum cassia, showed the chemical shifts of the aldehyde group as ${\delta}_H$ 9.7174 (9.7078, 9.7270) for the former compound and ${\delta}_H$ 9.6936 (9.6839, 9.7032) for the latter one. The difference of the chemical shift between two compounds was big enough to be distinguished using the NMR spectrometer with 0.45 Hz of resolution. The contents of cinnamaldehyde in Cinnamomum cassia, which were respectively extracted with n-hexane, $CHCl_3$, and EtOAc, were determiend as 94.2 \;mg/g (0.94%), 137.6 mg/g (1.38%) and 140.1 mg/g(1.40%) t-cinnamaldehyde in each extract, respectively, by using the above method.

Synthesis of C9-Alcohol through C9-Aldehyde Hydrogenation over Copper Catalysts (구리 촉매 상에서 C9-알데히드의 수소화 반응에 의한 C9-알코올 합성)

  • Park, Young-Kwon;Noh, Sang Gyun;Cho, Kyu Sang;Jeon, Jong-Ki
    • Korean Chemical Engineering Research
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    • v.44 no.4
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    • pp.363-368
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    • 2006
  • This study selected the optimal catalyst for the process of producing $C_9$-alcohol by hydrogenating $C_9$-aldehyde, and carried out an experiment in order to establish the operating condition for maximizing the yield of $C_9$-alcohol. The BET surface area and the specific area of copper were most excellent in $CuO/ZnO/Al_2O_3$ (60:30:10 wt%) catalyst produced using acetate as a precursor of copper and $Na_2CO_3$ as a precipitant, and the catalyst also showed the highest performance in $C_9$-aldehyde hydrogenation. Using a trickle bed reactor loaded with optimized catalyst, we attained 94.1 wt% yield of $C_9$-alcohol under the condition of $175^{\circ}C$, 800 psi and $WHSV=3hr^{-1}$. According to the result of comparing with other catalysts used in the hydrogenation of aldehyde, the catalyst showed similar performance to that of Ni/kieselghur and higher than that of $Cu-Ni-Cr-Na/Al_2O_3$ and $Ni-Mo/Al_2O_3$. According to the result of examining the stability of the catalyst through a long-term catalysis test, the yield of $C_9$-alcohol decreased slowly after around 72 hours due to the increasing production of high boiling-point byproducts.

A Study of $C_9$-aldehyde Synthesis from n-Butene (노르말부텐으로부터 $C_9$-알데히드 합성에 관한 연구)

  • Jeon, Jong-Ki;Park, Seong-Ki;Park, Young-Kwon
    • Clean Technology
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    • v.14 no.3
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    • pp.176-183
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    • 2008
  • The purpose of this study is to upgrade the catalysts for synthesizing mixed octenes using normal butene and the catalysts for synthesizing $C_9$-aldehyde through hydroformylation of mixed octenes with syngas. The in-line activation method with circulating activating solution was effective for activation of the $NiO/A1_{2}O_3$ catalyst. The reason for catalyst deactivation may be ascribed to physi-sorbed materials or oligomers which block pore entrance and then prevent active sites from participating a reaction. Continuous distillation apparatus was used for separating mixed octenes from dimerization products. When reflux ratio was above 3 : 1, mixed octene fraction of which purity was above 99.57% was obtained. In $C_9$-aldehyde synthesis through hydroformylation of mixed octenes, we investigated a performance of ligand which increased catalyst stability as well as activity of Co catalyst. The results indicated that TPPO, NMP, NDMA, and succinonitrile were suitable ligand for increasing initial activity and reducing loss of Co during catalyst recovery.

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Modified Direct-Sampling GLC Method to Study Warmed-Over Flavor Related Volatiles (휘발성(揮發性) Warmed-Over Flavor의 연구(硏究)를 위한 변형(變形)된 Direct Sampling GLC법(法))

  • Shin-Lee, Seung-Yee;Rhee, Chong-Ouk
    • Korean Journal of Food Science and Technology
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    • v.22 no.5
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    • pp.562-568
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    • 1990
  • The modified direct GLC method was evaluated for analysis of volatile compounds associated with WOF of cooked meat. This modified method was pertaining to collection of volatiles from the samples that contain quantities of water. The modification was appropriate for the studies of low molecular weight saturated aldehydes (C5-C15), unsaturated aldehydes (C5-C9), and saturated alcohols (C5-C9).

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Synthesis of Adenosine and Uridine Analogues Containing Conjugated Diene (공액 이중 결합을 갖는 Adenosine과 Uridine 유사체의 합성)

  • Ro, Bong Oh
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.312-317
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    • 2001
  • 7'-Aldehyde-nucleosides analogue (2a, 2c) were synthesized from 6-N-benzoyl-2',3'-O-isopropylideneadenosine and uridine. The condensation of 2 with ethoxycarbonylmethylene Wittig reagent produced the adenosine and uridine analogues containing extended conjugated diene and ethoxycarbonyl group, ethyl-1',5',6',7',8'-pentadeoxy-1'-(adenin-9-yl)-$\beta$-D-ribo-nona-5'(E),7'(E)-dienofuranuronate (4b) and ethyl-1'. 5',6',7',8'-pentadeoxy-1'-(uracil-1-yl)-$\beta$-D-ribo-nona-5'(E),7'-(E)-dienofuranuronate (4c). 9-[8',8'-dibromo-5',6',7',8' -tetradeoxy-$\beta$-D-ribo-octa-5'(E),7'(E)-diene]nucleosides (6b, 6c) were also prepared from 2 with similar method.

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Purification of Mitochondrial Matrix Aldehyde Dehydrogenase from Pig Brain

  • Kim, Kyu-Tae;Lee, Young-Don
    • BMB Reports
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    • v.28 no.2
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    • pp.177-183
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    • 1995
  • The activity of aldehyde dehydrogenase (ALDH) in the cerebrum, cerebellum, striatum, and medulla oblongata was examined and mitochondrial matrix ALDH was purified prior to immunohistochemical study on the localization of ALDH isozymes in pig brain. Relatively high enzyme activity was found in the striatum and medulla oblongata when using indole-3-acetaldehyde as substrate, and in the striatum when using 3,4-dihydroxyphenylacetaldehyde (DOPAL). The main part of mitochondrial ALDH activities with both acetaldehyde and DOPAL existed in the matrix fraction. The ratio of activity of the matrix to the membrane fraction in the cerebrum was higher than in the cerebellum, suggesting that the distribution pattern of ALDH isozymes was different according to the brain regions. The 276-fold purified mitochondrial matrix ALDH from pig brain was identified to be homologous tetramers with 53 KD subunits. The enzyme showed maximal activity at pH 9.0 and was stable in the temperature range from $25^{\circ}C$ to $37^{\circ}C$. The mitochondrial matrix ALDH activity was considerably inhibited by acetaldehyde in vitro. The $K_m$ values of the enzyme for acetaldehyde and propionaldehyde were 5.8 mM and 4.9 mM, respectively, whereas $K_m$ values for indole-3-acetaldehyde and DOPAL were 44 ${\mu}M$ and 1.6 ${\mu}M$, respectively. The $V_{max}/K_{m}$ ratio was the highest with DOPAL as compared with other substrates. These results suggested that mitochondrial matrix ALDH in the present work might be a low Km isozyme involved in biogenic aldehyde oxidation in pig brain.

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Optimized Conditions for In Situ Immobilization of Lipase in Aldehyde-silica Packed Columns

  • Seo Woo Yong;Lee Kisay
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.9 no.6
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    • pp.465-470
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    • 2004
  • Optimal conditions for the in situ immobilization of lipase in aldehyde-silica packed columns, via reductive amination, were investigated. A reactant mixture, containing lipase and sodium borohydride (NaCBH), was recirculated through an aldehyde-silica packed column, such that the covalent bonding of the lipase, via amination between the amine group of the enzyme and the aldehyde terminal of the silica, and the reduction of the resulting imine group by NaCBH, could occur inside the bed, in situ. Mobile phase conditions in the ranges of pH $7.0{\~}7.8$, temperatures between $22{\~}28^{circ}C$ and flow rates from $0.8{\~}1.5\;BV/min$ were found to be optimal for the in situ immobilization, which routinely resulted in an immobilization of more than 70 mg­lipase/g-silica. Also, the optimal ratio and concentration for feed reactants in the in situ immobilization: mass ratio [NaCBH]/[lipase] of 0.3, at NaCBH and lipase concentrations of 0.75 and 2.5 g/L, respectively, were found to display the best immobilization characteristics for concentrations of up to 80 mg-lipase/g-silica, which was more than a 2-fold increase in immobilization compared to that obtained by batch immobilization. For tributyrin hydrolysis, the in situ immobilized lipase displayed lower activity per unit mass of enzyme than the batch-immobilized or free lipase, while allowing more than a $45\%$ increase in lipase activity per unit mass of silica compared to batch immobilization, because the quantity of the immobilization on silica was aug­mented by the in situ immobilization methodology used in this study.

Volatile Flavor Components in Watermelon(Citrullus vulgaris S.) and Oriental Melon(Cucumis melo L.) (국내산 수박(Citrullus vulgaris S.) 과 참외(Cucumis melo L.) 의 휘발성 향기성분)

  • Kim, Kyong-Su;Lee, Hae-Jung;Kim, Sun-Min
    • Korean Journal of Food Science and Technology
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    • v.31 no.2
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    • pp.322-328
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    • 1999
  • Volatile flavor components of watermelon (Citrullus vulgaris S.) and oriental melon (Cucumis melo L.) obtained by simultaneous steam distillation and extraction apparatus were separated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS). Thirty seven and fifty five volatile flavor components were identified in watermelon and oriental melon, respectively. (Z)-3-Nonen-1-ol, (Z,Z)-3,6-nonadien-1-ol, (E,Z)-2,6-nonadienal and (E)-2-nonenal containing unsaturated nine carbon atoms were the characteristic flavor components of watermelon. $C_{9}-Unsaturated$ esters including (Z)-3-nonenyl acetate, (Z)-6-nonenyl acetate, (Z,Z)-3,6-nonadienyl acetate and thioester were important components in the flavor profile of oriental melon.

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The Effect of Saponins of Panax ginseng C.A. Meyer on Brain Aldehyde Dehydrogenase Activity of Ethanol Administered Rat (인삼사포인 성분이 에탄올을 투여한 쥐의 뇌 Aldehyde Dehydrogenase 활성에 미치는 영향)

  • 이영돈;주충노
    • Journal of Ginseng Research
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    • v.18 no.1
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    • pp.1-9
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    • 1994
  • Sprague-Dawley rats were given freely with 15% ethanol (control) and 15% ethanol containing (1) 0.1% ginseng saponin, (2) 0.02% ginsenoside $Rb_1$, and (3) $Rg_1$ (tests) instead of water for 7 days and aldehyde dehydrogenase (ALDH) and monoamine oxidase (MAO) activity in different regions of brain were examined. In control group, total ALDH activity with indoleacetaldehyde and acetaldehyde as substrate in all different regions was lower than that of normal group except in the hippocampus. The inhibitory effect on the activity was prominent in the corpus striatum and was not in the hippocampus. However, low-$K_m$ ALDH activity in all different regions was much lower than that of normal group. A considerable decrease in mitochondria ALDH activity in cerebellum and striatum was also observed in control group. In test groups total, low-$K_m$, and mitochondria AkDH activities in all different regions were higher than those in control group. Although ALDH activity in the striatum of test group was higher than control group, it was relatively depressed as compared with normal. There was not found a remarkable difference in extent of stimulating effect on the AkDH activity according to the ginseng saponin components. When biogenic aldehydes were used as substrate, ALDH activity with 3,4-dihydroxy-phenylacetaldehyde (DOPAL) in all brain regions of control group was lower than that using 5-hydroxy-indoleacetaldehyde (HIAL) and 3,4-dihydroxyphenylglycolaldehyde (NORAL) as substrate. In control group, ALDH activity with biogenic aldehydes above mentioned was markedly inhibited in the striatum contrary to other regions. The higher ALDH activity with biogenic aldehydes in test group than in control was found in the striatum, cerebrum, and cerebellum. MAO activity in the cerebellum was inhibited in control group and slightly increased in test group. The results of present study suggest that the corpus striatum is significantly affected by ethanol exposure while the hippocampus is not and that ginseng saponin fraction and ginsenosid es might have a preventive effect against depression of brain ALDH activity by chronic administration of ethanol.

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