• Title/Summary/Keyword: Allyl alcohols

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Allyl Alcohol Found in Heated Garlic is a Potent Selective Inhibitor of Yeasts

  • Lee Se-Hi;Woo Yong-Ho;Kyung Kyu-Hang
    • Journal of Microbiology and Biotechnology
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    • v.16 no.8
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    • pp.1236-1239
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    • 2006
  • Allyl alcohol (2-propen-l-ol), found in considerable amounts in heated garlic, was able to discriminate yeasts from bacteria and was approximately three orders of magnitude more inhibitory towards yeasts than bacteria. The average minimum inhibitory concentration (MIC) of allyl alcohol for bacteria and yeasts was 5.0% and 0.0056%, respectively. The unsaturated primary alcohols, including allyl alcohol and 2-buten-l-ol, seemed to work differently from all the other saturated alcohols and unsaturated secondary alcohols in inhibiting various yeasts. An alcohol dehydrogenase-negative (ADH$^-$) strain of Saccharomyces cerevisiae was as resistant to allyl alcohol as various bacteria, exhibiting an MIC of 5.0%. The unsaturated primary alcohols were apparently oxidized into the corresponding unsaturated aldehydes before they inhibited the yeasts.

Aliphatic and Allyl Alcohol-Induced Liver Cell Toxicity and its Detoxification

  • Park, Su-Kyung;Lee, Wan-Koo;Park, Young-Hoon;Moon, Jeon-Ok
    • Toxicological Research
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    • v.14 no.2
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    • pp.157-161
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    • 1998
  • The mechanism of active aldehyde-induced liver disease and the enzymatic basis of detoxification were investigated using normal rat liver cell, Ac2F. Aliphatic alcohols including l-decyl alcohol, l-nonanol, l-heptanol, l-hexanol, l-propanol and allyl alcohol exerted a dose- and time-de-pendent toxicity to Ac2F cells. The extent of their toxicities in buthionine sulfoximine (inhibitor of glutathione synthesis) pretreated cells was greater than in pargyline (inhibitor of aldehyde dehydrogenase, ALDH). On the other hand, the toxicity of these alcohols were not affected by 4-methylpyrazole (inhibitor of alcohol dehydrogenase, ADH). These results suggest that the contents of glutathione (GSH) seems to be very important in protecting the cells from toxicants such as aliphatic alcohols.

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Diastereoselective Synthesis of Unsaturated 1,4-Amino Alcohols as a Biologically Important Moiety

  • Jung Young Hoon;Kim Ji Duck
    • Archives of Pharmacal Research
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    • v.28 no.4
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    • pp.382-390
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    • 2005
  • chial allylic ethers with a hydroxyl group attached to the $\pi-system$ and chlorosulfonyl isocyanate. The enantioselectivity of the CSI reaction with the chiral allylic and benzylic ethers was examined in various solvents and temperatures. Based on these results, it was proposed that the CSI reaction is a competitive reaction of a $S_{N}i$ (retention) and a $S_{N}1$ mechanism (racemization) according to the stability of the carbocation intermediate. This means that there is a greater proportion of retention with the less stable the carbocation intermediate and vise versa.

A Study for Oxidation Reaction of Alcohols with Cr (Ⅵ)-Isoquinoline Compound (Ⅰ) (Cr (Ⅵ)-Isoquinoline 화합물에 의한 알코올들의 산화반응에 관한 연구 (Ⅰ))

  • Yang, Jeong Seong;Park, Yeong Jo;Baek, Hyeong Cheol
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.534-538
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    • 1990
  • Chromium(Ⅵ) compound, [$C_9H_7$NH]$_2Cr_2O_7$ has been prepared by the reaction of isoquinoline with chromium trioxide under the presence of water. [$C_9H_7$NH]$_2Cr_2O_7$ is nonhydroscopic and dissolved in water very well. Structure of [$C_9H_7$NH]$_2Cr_2O_7$ is identified by FTIR spectra and elemental analysis data. The ability of [$C_9H_7$NH]$_2Cr_2O_7$ for the oxidation of alcohols were examined in methylene chloride. [$C_9H_7$NH]$_2Cr_2O_7$ was found as efficient oxidizing agent for the conversion of allyl, primary and secondary alcohols to the corresponding aldehydes or ketones.

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Kinetic Study on the Oxidation Reaction of Alcohols by Cr(VI)-Quinoline Compound (크롬(VI)-퀴놀린 화합물에 의한 알코올류의 산화반응에 대한 반응속도론적 연구)

  • Park, Young-Cho;Kim, Soo-Jong
    • Journal of Convergence for Information Technology
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    • v.11 no.9
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    • pp.109-114
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    • 2021
  • Cr(VI)-quinoline compound[(C9H7NH)2Cr2O7] was synthesized by the reaction between of quinoline and chromium(VI) trioxide, and structure was FT-IR, elemental analysis. The oxidation ability of benzyl alcohol greatly depends upon the dielectric constant of the used organic solvent, where carbon tetrachloride was worst and N,N'-dimethylformamide was best solvent. Noticeably, in N,N'-dimethylformamide solvent, Cr(VI)-quinoline compound oxidized substituted benzyl alcohols. The Hammett reaction constant(ρ)=-0.69(303K). As a resuit, Cr(VI)-quinoline compound was found as efficicent oxidizing agent that converted benzyl alcohol, allyl alcohol, primary alcohol and secondary alcohols to the corresponding aldehydes or ketones. Cr(VI)-quinoline compound was selective oxidizing agent of benzyl alcohol, allyl alcohol and primary alcohol in the presence of secondary alcohol ones.

Comparison of Volatile Organic Components in Fresh and Freeze Dried Garlic (생마늘과 동결건조마늘의 휘발성 유기성분 비교)

  • Kim, Youn-Soon;Seoa, Hye-Young;No, Ki-Mi;Shim, Sung-Lye;Yang, Su-Hyeong;Park, Eun-Ryong;Kim, Kyong-Su
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.34 no.6
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    • pp.885-891
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    • 2005
  • The study was carried out to find the effect of freeze drying on the volatile organic components in garlic (Allium sativum L.). The volatile organic compounds from fresh and freeze dried garlic were extracted by simultaneous steam distillation and extraction (SDE) method and identified with GC/MS analysis. A total of 42 and 32 compounds were identified in fresh and freeze-dried garlic, respectively. Sulfur containing compounds in the garlic samples were detected as the major compounds, and alcohols, aldehydes and esters were detected as minor compounds. Diallyl disulfide, diallyl trisulfide, allyl methyl disulfide and ally1 methyl trisulfide were the main sulfur compounds in fresh and freeze dried garlic. The amount of sulfur containing compounds were decreased freeze-drying but methyl propyl trisulide, 3- allylthiopropionic acid, cyclopentyl ethyl sulfide etc. were increased. The others, non- sulfur containing compounds such as ethyl acetate, ethanol, 2-propenol, 2- propenal and hexanal were increased in freeze-dried garlic. Consequently, the total amount of volatile organic compounds in garlic became lower during freeze-drying from 853.42 mg/kg to 802.21 /kg, and the composition of major components were nearly same in fresh and freeze-dried garlic.

Effect of γ-Irradiation on the Volatile Organic Compounds from Leek (Allium tuberosum R.) (부추(Allium tuberosum R.)의 감마선 조사에 의한 휘발성 유기화합물의 성분 변화)

  • Han, Byung-Jae;Yang, Sook-Young;Kim, Jun-Hyoung;Shim, Sung-Lye;Gyawali Rajendra;Lee, Sung-Jin;Kim, Kyong-Su
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.34 no.4
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    • pp.513-518
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    • 2005
  • Volatile compounds of $\gamma-irradiation$ leeks (Aillum tuberosum R.) were isolated by simultaneous steam distillation and extraction method (SDE) and analyzed by gas chromatography/mass spectrometry (GC/MS) along with the non-irradiated sample. Leeks were irradiated at dose of 20 kGy and non-irradiated samples were considered as control sample. 56 and 54 compounds were identified in non-irradiated and irradiated samples, respectively. These components included the functional groups; alcohols, aldehydes, esters, ketones, N- and S-containing compounds. S-containing compounds such as dimethyl trisulfide, methyl-(Z)-l-proenyl trisulfide, dimethyl disulfide, 3-ethyl-l,2-dithi-5-ene and methyl allyl disulfide were the major compounds. Methyl-(Z)-l-propenyl trisulfide, diallyl trisulfide, (E)-2-hexanal and 3-ethyl-l,2-dithi-5-ene were clearly decreased by the $\gamma-irradiation$, but dimethyl disulfide, diallyl sulfide, allyl methyl sulfide and pyridine were increased by the $\gamma-irradiation$.

Volatile Flavor Components of Leek(Allium tuberosum Rottler) (부추(Allium tuberosum Rottler)의 휘발성 향기성분)

  • 김경수;박은령;조정옥;김선민;이명렬
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.27 no.4
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    • pp.563-567
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    • 1998
  • Volatile flavor components of edible portion of leek(Allium tuberosum R.) were extracted by SDE(simultaneous steam distillation and extraction) method using the mixture of n-pentane and diethylether (1 : 1, v/v) as an extract solvent and analyzed by GC-FID and GC/MS. Identification of the volatile flavor components was mostly based on the RI of GC and mass spectrum of GC/MS. A total of sixty-five components from leek extract were classified as 28 sulfur-containing compounds, 12 aldehydes, 9 alcohols, 4 lactones and esters, 3 acids and hydrocarbons, and 2 miscellaneous compouds. The sulfur-containing compounds were predominant in leek extract. Dimethyl disulfide(19.47%) and dimethyl trisulfide(17.38%) were the main compounds and trans-1-propenyl methyl disulfide, trans-2-hexenal and methyl allyl disulfide were also detected large amounts in leek.

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Kinetics and Mechanism of the Oxidation of Alcohols by C9H7NHCrO3Cl (C9H7NHCrO3Cl에 의한 알코올류의 산화반응에서 속도론과 메카니즘)

  • Park, Young-Cho;Kim, Young-Sik;Kim, Soo-Jong
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.19 no.8
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    • pp.378-384
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    • 2018
  • $C_9H_7NHCrO_3Cl$ was synthesized by reacting $C_9H_7NH$ with chromium (VI) trioxide. The structure of the product was characterized by FT-IR (Fourier transform infrared) spectroscopy and elemental analysis. The oxidation of benzyl alcohol by $C_9H_7NHCrO_3Cl$ in various solvents showed that the reactivity increased with increasing dielectric constant(${\varepsilon}$) in the following order: DMF (N,N'-dimethylformamide) > acetone > chloroform > cyclohexane. The oxidation of alcohols was examined by $C_9H_7NHCrO_3Cl$ in DMF. As a result, $C_9H_7NHCrO_3Cl$ was found to be an efficient oxidizing agent that converts benzyl alcohol, allyl alcohol, primary alcohols, and secondary alcohols to the corresponding aldehydes or ketones (75%-95%). The selective oxidation of alcohols was also examined by $C_9H_7NHCrO_3Cl$ in DMF. $C_9H_7NHCrO_3Cl$ was the selective oxidizing agent of benzyl, allyl and primary alcohol in the presence of secondary ones. In the presence of DMF with an acidic catalyst, such as $H_2SO_4$, $C_9H_7NHCrO_3Cl$ oxidized benzyl alcohol (H) and its derivatives ($p-OCH_3$, $m-CH_3$, $m-OCH_3$, m-Cl, and $m-NO_2$). Electron donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.69 (308K). The observed experimental data were used to rationalize hydride ion transfer in the rate-determining step.