• Applied Chemistry for Engineering
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• v.18 no.6
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• pp.562-567
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• 2007

The stereoselective synthesis of chiral terminal epoxide is of immense academic and industrial interest due to their use as versatile starting materials as well as chiral intermediates. In this study, new polymeric chiral Co(salen) complexes bearing tallium (III)chloride and iron (III)chloride (ferric chloride) have been synthesized and characterized. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of various terminal epoxides using water and phenol derivatives as nucleophiles. The easily prepared polymeric complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ and phenol nucleophiles, providing enantiomerically enriched terminal epoxides (> 98% ee). The system described in this work is very efficient for the synthesis of chiral epoxide, 1,2-diol and ${\alpha}$-aryloxy alcohol intermediates.

• Bulletin of the Korean Chemical Society
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• v.27 no.11
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• pp.1747-1751
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• 2006

The dinuclear tetraazadiphenol macrocyclic nickel(II) complexes [$Ni_2$([20]-DCHDC)]$Cl_2$ (I), [$Ni_2$([20]-DCHDC)]$(ClO_4)_2{\cdot}2CH_3CN $ (II(b)) and [$Ni_2$([20]-DCHDC)$(NCS)_2$] (III) {$H_2$[20]-DCHDC = 14,29-dimethyl-3,10,18,25-tetraazapentacyclo-[25,3,1,$0^{4,9}$,$1^{12,16}$,$0^{19,24}$]ditriacontane-2,10,12,14,16(32),17,27(31), 28,30-decane-31,32-diol} have been synthesized by self-assembly and characterized by elemental analyses, conductances, FT-IR and FAB-MS spectra, and single crystal X-ray diffraction. The crystal structure of II(b) is determined. It crystallizes in the monoclinic space group P2(1)/c. The coordination geometries around Ni(II) ions in I and II(b) are identical and square planes. In complex III each Ni(II) ion is coordinated to $N_2O_2$ plane from the macrocycle and N atoms of NCS- ions occupying the axial positions, forming a square pyramidal geometry. The nonbonded Ni…Ni intermetallic separation in the complex II(b) is 2.8078(10) $\AA$. The FAB mass spectra of I, II and III display major fragments at m/z 635.1, 699.4 and 662.4 corresponding to [$Ni_2$([20]-DCHDC)(Cl + 2H)]$^+$, [$Ni_2$([20]-DCHDC)$(ClO_4\;+\;2H)]^+$ and [$Ni_2$([20]-DCHDC)(NCS) + 6H]$^+$, respectively.

• Bulletin of the Korean Chemical Society
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• v.10 no.4
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• pp.382-388
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• 1989

The approximate rates and stoichiometry of the reaction of excess potassium tri-sec-butylborohydride ($K_s-Bu_3BH$) with selected organic compounds containing representative functional groups were determined under the standard conditions (0$^{\circ}C$, THF) in order to define the characteristics of the reagent for selective reductions. Primary alcohols evolve hydrogen in 1 h, but secondary and tertiary alcohols and amines are inert to this reagent. On the other hand, phenols and thiols evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of norcamphor gives 99.3% endo- and 0.7% exo-isomer of norboneols. The reagent rapidly reduces cinnamaldehyde to the cinamyl alcohol stage and shows no further uptake of hydride. p-Benzoquinone takes up one hydride rapidly with 0.32 equiv hydrogen evolution and anthraquinone is cleanly reduced to the 9,10-dihydoxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively, however further reduction does not occur. Anhydrides utilize 2 equiv of hydride and acyl chlorides are reduced to the corresponding alcohols rapidly. Lactones are reduced to the diol stage rapidly, whereas esters are reduced moderately (3-6 h). Terminal epoxides are rapidly reduced to the more substituted alcohols, but internal epoxides are reduced slowly. Primary and tertiary amides are inert to this reagent and nitriles are reduced very slowly. 1-Nitropropane evolves hydrogen rapidly without reduction and nitrobenzene is reduced to the azoxybenzene stage, whereas azobenzene and azoxybenzene are inert. Cyclohexanone oxime evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine and quinoline are reduced slowly, however pyridine N-oxide takes up 1.5 equiv of hydride in 1 hr. Disulfides are rapidly reduced to the thiol stage, whereas sulfide, sulfoxide, sulfonic acid and sulfone are practically inert to this reagent. Primary alkyl bromide and iodide are reduced rapidly, but primary alkyl chloride, cyclohexyl bromide and cyclohexyl tosylate are reduced slowly.

• Journal of Integrative Natural Science
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• v.14 no.3
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• pp.99-106
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• 2021

A mixture of alcohol and water is commonly used as antifreeze, liquor, and the fundamental solvents for the manufacture of cosmetics, pharmaceuticals, and inks in our daily life. Since various properties of alcohol water mixtures such as density, boiling or melting point, viscosity, and dielectric constant are determined by their mixing ratio, it is very important to know the mixing ratio to predict their properties. One of simple method to find the mixing ratio is measuring the density of the mixtures. However, it is not easy to predict the mixing ratio from the density of the mixtures because the relationship between mixing ratio and density has not been established well. The relationship is dependent on the relative sizes of solute and solvent molecules, and their interactions. Recently, an empirical model to predict the density of glycerol water mixture from their mixing ratio has been introduced. The suggested model is simple but quite accurate for glycerol water mixture. In this article, we investigated the applicability of this model to different alcohol water mixtures. Densities for six different alcohol water mixtures containing various alcohols (e.g., ethylene glycol, 1,3-propane diol, propylene glycol, methanol, ethanol, and 1-propanol) were simulated and compared to experimentally measured ones to investigate the applicability of the model proposed for glycerol water mixtures to other alcohol water mixtures. The model predicted the actual density of all alcohol water mixtures tested in this article with high accuracy at various ratios. This model can probably be used to predict the mixing ratio of other alcohol water mixtures from their densities beyond 6 alcohols tested in this article from their densities.

• Journal of Microbiology and Biotechnology
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• v.29 no.2
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• pp.191-199
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• 2019

We inoculated different combinations of three starter candidates, Bacillus licheniformis, Staphylococcus succinus, and Tetragenococcus halophilus, into sterilized soybeans to predict their contributions to volatile compound production through soybean fermentation. Simultaneously, we added NaCl to soybean cultures to evaluate its effect on the volatile compounds profile. Cells in soybean cultures (1.5% NaCl) nearly reached their maximum growth in a day of incubation, while cell growth was delayed by increasing NaCl concentrations in soybean cultures. The dominance of B. licheniformis and S. succinus in the mixed cultures of three starter candidates switched to T. halophilus as the NaCl concentration increased from 1.5% to 14% (w/w). Seventeen volatile compounds were detected from the control and starter candidate-inoculated soybean cultures with and without the addition of NaCl. Principal component analysis of these volatile compounds concluded that B. licheniformis and S. succinus made major contributions to producing a specific volatile compound profile from soybean cultures where both species exhibited good growth. 3-Hydroxybutan-2-one, butane-2,3-diol, and 2,3,5,6-tetramethylpyrazine are specific odor notes for B. licheniformis, and 3-methylbutyl acetate and 2-phenylethanol are specific for S. succinus. Octan-3-one and 3-methylbutan-1-ol were shown to be decisive volatile compounds for determining the involvement of S. succinus in the soybean culture containing 7% NaCl. 3-Methylbutyl acetate and 3-methylbutan-1-ol were also produced by T. halophilus during soybean fermentation at an appropriate level of NaCl. Although S. succinus and T. halophilus exhibited growth on the soybean cultures containing 14% NaCl, species-specific volatile compounds determining the directionality of the volatile compounds profile were not produced.

• Mycobiology
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• v.51 no.4
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• pp.246-255
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• 2023

Genus Penicillium comprising the most important and extensively studied fungi has been well-known as a rich source of secondary metabolites. Our study aimed to analyze and investigate biological activities, including in vitro anti-cancer, anti-inflammatory and anti-diabetic properties, of metabolites from a marine-derived fungus belonging to P. levitum. The chemical compounds in the culture broth of P. levitum strain N33.2 were extracted with ethyl acetate. Followingly, chemical analysis of the extract leaded to the isolation of three ergostane-type steroid components, namely cerevisterol (1), ergosterol peroxide (2), and (3β,5α,22E)-ergosta-6,8(14),22-triene-3,5-diol (3). Among these, (3) was the most potent cytotoxic against human cancer cell lines Hep-G2, A549 and MCF-7 with IC₅₀ values of 2.89, 18.51, and 16.47 ㎍/mL, respectively, while the compound (1) showed no significant effect against tested cancer cells. Anti-inflammatory properties of purified compounds were evaluated based on NO-production in LPS-induced murine RAW264.7 macrophages. As a result, tested compounds performed diverse inhibitory effects on NO production by the macrophages, with the most significant inhibition rate of 81.37±1.35% at 25 ㎍/mL by the compound (2). Interestingly, compounds (2) and (3) exhibited inhibitory activities against pancreatic lipase and α-glucosidase enzymes in vitro assays. Our study brought out new data concerning the chemical properties and biological activities of isolated steroids from a P. levitum fungus.

• Journal of Ginseng Research
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• v.44 no.3
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• pp.405-412
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• 2020

Background: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. Methods: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. Results and Conclusion: Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3β,6α,12β,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6α,12β,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3β,6α,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12β,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6α-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

• Journal of the Korean Chemical Society
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• v.37 no.11
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• pp.967-973
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• 1993

${\alpha},{\omega}$-Diols such as 1,6-hexanediol and 1,7-heptanediol react with secondary amines in the presence of catalytic amount of ruthenium complex at 180$^{\circ}$C for 24 hrs to give the corresponding diamino compounds in good yields. The yield of diamino compound was affected by the molar ratio of ${\alpha},{\omega}$-diol to secondary amine. The reaction was also affected by the nature of the phosphorus ligands employed. On the other hand, aromatic primary amines react with 1,2,6-hexanetriol in the presence of RuCl_3{\cdot}H_2O-3PPh_3$ at 180$^{\circ}$C for 3 hours under argon atmosphere to give selectively 1-substituted aryl-3-hydroxyperhydroazepines in good yields. Selective synthesis of these products show that two primary hydroxy groups (1,6-positions) oxidize predominantly than secondary hydroxy group (2-position) by ruthenium-phosphorus complex. The yields were decreased according to the order of para-, meta- and ortho-substituent.

• Korean Journal of Food Science and Technology
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• v.39 no.6
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• pp.593-599
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• 2007

In this study, we examined the volatile flavor components in the mashes of takju prepared using different yeasts such as Saccharomyces coreanus, S. ellipsoideus, S. carlsbergensis, S. cerevisiae (Baker's yeast), and S, rouxii by GC and GC-MS. Fourteen alcohols, 13 esters, 5 acids, 3 aldehydes, 7 amines, and 2 other compounds were identified in the mash after 6 days of fermentation. On day 6, the takju fermented by S. coreanus had the greatest variety of volatile flavor components. Fifteen flavor components, including ethanol, isobutyl alcohol, isoamyl alcohol, methyl pentanol, 1,3-butanediol, 3-methylthio-1-propanol, benzeneethanol, ethyl lactate, acetic acid, acetaldehyde, and 1,3-cyclohexane diamine, were typically detected in all the treatments. The relative peak areas of the volatile components were as follows: alcohols (96.758-99.387%), esters (0.081-0.968%), acids (0.040-0.640%), aldehydes (0.266-0.959%), and amines (0.011-0.047%). In particular, 1-propanol, isobutyl alcohol, 3-methyl-1-butanol, 2,3-butanediol, trimethyl benzylalcohol, heptene-2,4-diol, ethyl lactate, diethyl succinate, ethyl nonanoate, methyl hexadecanoate, linoleic acid, hexadecanoic acid, and acetaldehyde were hish in the takju made by S. coreanus. Also, ethyl stearate was high in the takju made by S. carlsbergensis, and hexanoic acid was high in the takju made by S. cerevisiae. Finally, methyl pentanol, 1,3-butanediol, 3-methylthio-1-propanol, benzene ethanol, ethyl octadecanoate, acetic acid, pentanal, and 1,3-cyclohexane diamine were high in the takju made by S. rouxii.

• Polymer(Korea)
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• v.38 no.4
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• pp.441-448
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• 2014

Polyurethane/melamine phosphate composite foam (MP-PUF) was prepared from poly(adipate)diol/melamine phosphate composite (f=2), polyether-polyol (f=4.6), and PMDI (f=2.5). The thermal properties of MP-PUF such as morphology, closed-cell content, thermal conductivity, and thermal stabilities were characterized. Water was used as a blowing agent, and the composition of melamine phosphate (MP) was maintained at $1.43{\pm}0.3wt%$ of MP-PUF. As the content of water increased, the thermal conductivity of pure polyurethane foam (PUF) decreased, whereas the thermal conductivity of MP-PUF increased. The thermal stabilities of the PUF and the MP-PUF were maximized at 5 php $H_2O$, and then decreased at the higher $H_2O$ contents. The thermal stabilities of MP-PUF were greatly enhanced due to the synergetic effect of MP and urea, which was generated during the blowing process. The temperature of 50% residual mass of MP-PUF increased to $370{\sim}450^{\circ}C$ and the temperature of 30% residual mass exceeded over $700^{\circ}C$. Compared to the PUF, the temperature of 50% residual mass and 30% residual mass were higher than 25 and $70^{\circ}C$, respectively.