• Title/Summary/Keyword: double bond

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Compositional Characterization of Petroleum Heavy Oils Generated from Vacuum Distillation and Catalytic Cracking by Positive-mode APPI FT-ICR Mass Spectrometry

  • Kim, Eun-Kyoung;No, Myoung-Han;Koh, Jae-Suk;Kim, Sung-Whan
    • Mass Spectrometry Letters
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    • v.2 no.2
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    • pp.41-44
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    • 2011
  • Molecular compositions of two types of heavy oil were studied using positive atmospheric pressure photoionization (APPI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). Vacuum gas oil (VGO) was generated from vacuum distillation of atmospheric residual oil (AR), and slurry oil (SLO) was generated from catalytic cracking of AR. These heavy oils have similar boiling point ranges in the range of 210-$650^{\circ}C$, but they showed different mass ranges and double-bond equivalent (DBE) distributions. Using DBE and carbon number distributions, aromatic ring distributions, and the extent of alkyl side chains were estimated. In addition to the main aromatic hydrocarbon compounds, those containing sulfur, nitrogen, and oxygen heteroatoms were identified using simple sample preparation and ultra-high mass resolution FT-ICR MS analysis. VGO is primarily composed of mono- and di-aromatic hydrocarbons as well as sulfur-containing hydrocarbons, whereas SLO contained mainly polyaromatic hydrocarbons and sulfur-containing hydrocarbons. Both heavy oils contain polyaromatic nitrogen components. SLO inludes shorter aromatic alkyl side chains than VGO. This study demonstrates that APPI FT-ICR MS is useful for molecular composition characterization of petroleum heavy oils obtained from different refining processes.

Flavonoids: Potential Antiinflammatory Agents

  • Kim, Hyun-Pyo;Son, Kun-Ho;Chang, Hyun-Wook;Kang, Sam-Sik
    • Natural Product Sciences
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    • v.2 no.1
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    • pp.1-8
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    • 1996
  • Flavonoids are widely distributed polyphenol compounds in plant kingdom and known to possess varieties of biological/pharmacological activities in vitro and in vivo. A search for antiinflammatory/immunoregulatory flavonoids as potential therapeutic agents has been continued, since serious side effects of currently used nonsteroidal and steroidal antiinflammatory drugs limit their long term uses for the inflammatory disorders. In this reserch, various flavonids were isolated and tested for their in vivo antiinflammatory activity and in vitro inhibitory activity of lymphocyte proliferation. Using a mouse ear edema assay, it was found that certain flavones/flavonols possess mild antiinflammatory activity and a C-2,3-double bond might be essential. Isoflavones were less active. These flavonoids inhibited in vitro lymphocyte proliferation, relatively specific for T-cell proliferation $(IC_{50}=1-10\;{\mu}M)$ and the inhibition was reversible. We have also tested several biflavonoid derivatives, since we recently found that biflavones were phospholipase $A_2$ inhibitors. It was demonstrated that biflavones such as ochnaflavone and ginkgetin inhibited lymphocyte proliferation induced by both concanavaline A and lipopolysaccharide. The inhibition was irreversible in contrast to that of flavones/flavonols. And antiinflammatory activity of biflavonoids are discussed.

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Microbial styrene monooxygenase-catalyzed asymmetric synthesis of enantiopure styrene oxide derivatives (미생물 유래 Styrene monooxygenase를 이용한 광학활성 styrene oxide 유도체의 비대칭합성)

  • Lee, Eun-Yeol;Park, Sung-Hoon
    • KSBB Journal
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    • v.24 no.3
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    • pp.239-245
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    • 2009
  • Enantiopure styrene oxide derivatives are versatile building blocks for the synthesis of enantiopure pharmaceuticals. Styrene monooxygenase (SMO) catalyzes an asymmetric addition of an oxygen atom into a double bond of vinylaromatic compounds. SMO is a commercially potential biocatalyst to synthesize a variety of enantiopure epoxides with high enantiopurity and recovery yield. In this paper development of SMO biocatalyst and commercial feasibility of SMO-catalyzed asymmetric synthesis of enantiopure stylers oxide derivatives are reviewed.

Kinetic Studies on the Nucleophilic Addition of Cysteine to 3,4-Methylenedioxyphenylmethylene Malononitrile (3,4-Methylenedioxyphenylmethylene Malononitrile에 대한 Cysteine의 친핵성 첨가반응에 관한 반응속도론적 연구)

  • Tae-Rin Kim;Dong-Suk Rho;Young-Haeng Lee
    • Journal of the Korean Chemical Society
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    • v.26 no.6
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    • pp.407-413
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    • 1982
  • The rate constants of the nucleophilic addition of cysteine to 3,4-methylenedioxyphenylmethylene malononitrile were determined by UV Spectrophotometry and a rate equation which can be applied over wide pH range was obtained. On the basis of rate equation, it may be concluded that the rate constants were dependent upon only the concentration of hydroxide ion above pH 9.0, however, below pH 6.0, the reaction were initiated by the addition of neutral cysteine molecule to carbon-carbon double bond and at pH 7.0~9.0, the addition of a neutral cysteine molecule and it's anion occurred competitively.

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Antimutagenic Effect of Plant Flavonoids in the Salmonella Assay System

  • Choi, Jae-Sue;Park, Kun-Young;Moon, Suk-Hee;Rhee, Sook-Hee;Young, Han-Suk
    • Archives of Pharmacal Research
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    • v.17 no.2
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    • pp.71-75
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    • 1994
  • The antimutagenic effects of 27 kinds of plant flavonoids on the mutagenicity of aflatoxin $B_1(AFB_1)$ and N-methyl-N'-nitro-N-nitrosoguanidine(MANG) in Salmonella typhimurium TA 100 were investigated. In the mixed applications of $AFB_1\;(1\;\mu{g/plate)}$ with the flavonoids $(300\;\mu{g/plate)}$ in the presence of a mammalian metabolic activation system (S9 mix), chrysin, apigenin, luteolin and its glucoside, kaempferol, fisetin, morin, naringenin, hesperetin, persicogenin, (+)-catechin and (-)epicatechin showed the antimutagenic effect against $AFB_1$ with more than 70% inhibition rate. A little or no antimutagenicities except flavone against MNNG $(0.5\;\mu{g/plate)}$ were observed. For the antimutagencity of the flavonoids on $AFB_1$, the flavonoid structure that contains the free 5, 7-hydroxyl gorup seemed to be essential. However, saturation of the 2, 3-double bond of elimination of the 4-keto group did not affect the activity.

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Protective effect of ginsenoside Rh3 against anticancer drug-induced apoptosis in LLC-PK1 kidney cells

  • Lee, Hye Lim;Kang, Ki Sung
    • Journal of Ginseng Research
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    • v.41 no.2
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    • pp.227-231
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    • 2017
  • Background: Ginsenosides are active components of Panax ginseng that exert various health benefits including kidney protection effect. The medicinal activity of ginsenosides can be enhanced by modulating their stereospecificity by heat processing. Ginsenosides Rk2 and Rh3 represent positional isomers of the double bond at C-20(21) or C-20(22). Methods: The present study investigated the kidney-protective effects of ginsenosides Rk2 and Rh3 against cisplatin, a platinum based anticancer drug, induced apoptotic damage in renal proximal LLC-PK1 cells. Results: As a result, ginsenoside Rh3 shows a stronger protective effect than that shown by Rk2. Cisplatin-induced elevated protein levels of phosphorylated c-Jun N-terminal kinase (JNK), extracellular signal-regulated kinase (ERK), p38, and cleaved caspase-3 decreased after cotreatment with ginsenoside Rh3. The increase in the percentage of apoptotic LLC-PK1 cells induced by cisplatin treatment also significantly reduced after cotreatment with ginsenoside Rh3. Conclusion: These results demonstrate that inhibition of the JNK and ERK mitogen-activated protein kinase signaling cascade plays a critical role in mediating the renoprotective effect of ginsenoside Rh3.

Influence of Wax Molecular Weights on Wax Migration and Evaporation of Rubber Vulcanizates at Room Temperature (상온 노화 후 고무가황물에서 왁스의 이동과 증발에 미치는 왁스의 분자량 분포)

  • Im, Song-Hee;Choi, Sung-Seen
    • Elastomers and Composites
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    • v.44 no.4
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    • pp.397-400
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    • 2009
  • Ozone caused the crack on the surface of a rubber article by oxidation of double bond at room temperature. Wax migrates to the surface of a rubber article and makes a physical barrier to prevent process of ozonation. We investigated change of molecular weight distribution of waxes in unfilled NR, SBR, and BR vulcanizates before and after aging at room temperature for 6 months. Migration and evaporation behaviors of wax in a rubber article at ambient conditions help understand a role of wax as an antidegradant and appearance contamination of a rubber article. The relative intensity distribution of n-alkanes of the NR specimen after the aging was shifted to higher molecular weight compared with the relative intensity distribution before the aging, while those of the SBR specimen before and after the aging did not show a big difference.

Occurrence of cis-4-Tetradecenoic Acid in the Oils of Kernels of Lindera erythrocarpa Seeds, as a Major Component

  • Kim, Seong-Jin;Joh, Yong-Goe
    • Food Science and Biotechnology
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    • v.15 no.1
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    • pp.107-111
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    • 2006
  • Kernel oils of Lindera erythrocarpa seeds had high level of unusual fatty acid. Picolinyl ester of this unknown fatty acid showed molecular ion at m/z = 317 with other diagnostic ions such as m/z = 151, 191 (40 amu between two peaks), 204, and 218 on GC-MS. Characteristic peak at $720\;cm^{-1}$ appeared in IR spectrum. In $^1H-NMR$ spectrum both methylene protons at C-3 and C-6 resonated at ${\delta}2.309$ and ${\delta}2.012$, and methine protons of double bond resonated in lower magnetic field centered at ${\delta}5.296$ (C-4) and ${\delta}5.387$ (C-5) as multiplet (J = 9.7Hz). In $^{13}C-NMR$, signals at ${\delta}22.669$ and ${\delta}27.048$ were due to C-3 and C-6 of ${\delta}^4$-monoenoic acid. Results obtained from spectroscopic measurements confirmed unknown fatty acid as cis-4-tetradecenoic acid (cis-4-$C_{14:1}$). Main fatty acid components of oils were cis-4-$C_{14:1}$ (44.5-45.1%), oleic acid ($C_{18:1}$), 20.4-21.3%), and lauric acid ($C_{12:0}$, 11.6-12.4%), along with trace amounts of cis-4-$C_{12:1}$ and cis-4-$C_{16:1}$.

The Kinetics and Mechanism of the Hydrolysis to Thienyl Chalcone Derivatives (Thienyl Chalcone 유도체의 가수분해 반응메카니즘과 그 반응속도론적 연구)

  • Hwang, Yong-Hyun;Lee, Ki-Chang;Kim, Jin-Yeong
    • Journal of the Korean Applied Science and Technology
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    • v.10 no.2
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    • pp.73-80
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    • 1993
  • The hydrolysis reaction kinetics of 2-thienyl chalcone derivatives $[II]{\sim}[V]$ was investigated by ultraviolet spectrophotometery in 20% dioxane-$H_2O$ at $25^{\circ}C$ and the structure of these compounds were ascertained by means of ultraviolet, infrared and NMR spectra. The rate equations which were applied over a wide pH range(pH $1.0{\sim}13.0$) were obtained. The substituent effects on 2-thienyl chalcone derivatives$[II]{\sim}[V]$ were studied, and the hydrolysis were facilitated by electron attracting groups. On the basis of the rate equation, substitutent effect and final product, the plausible hydrolysis reaction mechanism was proposed : At pH $1.0{\sim}9.0$, not relevant to the hydrogen ion concentration, neutral $H_2O$ molecule competitvely attacked on the double bond. By contraries, above pH 9.0, it was proportional to concentration of hydroxide ion.

The Kinetics and Mechanism of the Hydrolysis to Benzoyl Styrene Derivatives (Benzoyl Styrene 유도체의 가수분해 반응 메카니즘과 그 반응속도론적 연구)

  • Lee, Ki-Chang;Yoon, Chul-Hun;Hwang, Sung-Kwy;Oh, Se-Young
    • Journal of the Korean Applied Science and Technology
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    • v.12 no.1
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    • pp.35-41
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    • 1995
  • The Hydrolysis kinetics of Benzoyl Styrene Derivatives[I]${\sim}$[IV] was investigated by ultraviolet spectrophotometery in 5% dioxane-$H_2O$ at $40^{\circ}C$. The structure of these compounds were ascertained by means of ultraviolet, melting point, IR and NMR spectra. The rate equations which were applied over a wide pH range (pH $1.0{\sim}13.0$) were obtained. The substituent effects on Benzoyl styrene derivatives[I]${\sim}$[IV] were studied, and the hydrolysis were facilitated by electron attracting groups. On the basis of the rate equation and substitutent effect and final product, the plausible hydrolysis reaction mechanism was proposed: At pH 1.0${\sim}$pH 9.0, not relevant to the hydrogenl ion concentration, neutral $H_2O$ molecule competitively attacked on the double bond. By contrary. Above pH 9.0, It was proportional to concentration of hydroxidel ion.