• Bulletin of the Korean Chemical Society
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• v.7 no.4
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• pp.296-298
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• 1986

Carboxylic acid anhydrides are rapidly reduced with borane-lithium chloride (1:0.1) system to give corresponding alcohols (diols in the case of cyclic anhydride) quantitatively in tetrahydrofuran at room temperature. This reagent tolerates aromatic acid ester, nitro, and halide functional groups, however competitively reduces aliphatic ester and nitrile groups.

• Bulletin of the Korean Chemical Society
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• v.27 no.8
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• pp.1203-1205
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• 2006

During the synthesis of 4-fluorobenzaldehyde via the SNAr reaction of 4-nitrobenzaldehyde with TBAF, it was found that an equivalent amount of TBAF could oxidize benzaldehyde to benzoic acid. The reaction of 4-nitrobenzaldehyde with tetrabutylammonium fluoride (TBAF) gave 4-nitrobenzoic acid in high yield. Depending on the reaction conditions, other aromatic aldehydes produced acids with fewer amounts of alcohols. However, this type of oxidation has limited practical applications. Nevertheless, the mechanism is quite different from the Cannizzaro reaction because the amounts of the acid salt and alcohol formed were different.

• Fisheries and Aquatic Sciences
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• v.4 no.4
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• pp.229-237
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• 2001

In order to identify of volatile flavor compounds and polycyclic aromatic hydrocarbons (PAHs) in commercial liquid smokes, this study was conducted to analyze volatile flavor compounds by solvent extraction and/or Purge & Trap method/GC/MSD. A total of 156 volatile flavor compounds were detected in 6 commercial liquid smokes, and these compounds were composed mainly of 12 aldehydes, 60 ketones, 7 alcohols, 14 acids, 20 esters, 24 aromatic compounds, 7 furans and 12 miscellaneous compounds. Ketones $(806.6-7,573.9\mu g/mL)$ and aromatic compounds $(282.6-7,896.3 \mu g/mL)$ were more abundant than others. The PAHs known as carcinogen have not been detected in this study. The acids $(422.9-4,903.1\mu g/mL)$ was identified in relatively high concentration compared to other groups. Phenol and its derivatives among aromatic compounds were in relatively high concentration. Especially, the phenol and its derivatives including o-cresol, guaiacol, 4-ethylguaiacol and syringol were in higher concentration.

• Bulletin of the Korean Chemical Society
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• v.15 no.10
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• pp.881-888
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• 1994

The approximate rates and stoichiometry of the reaction of excess sodium tris(diethylamino)aluminum hydride (ST-DEA) with selected organic compounds containing representative functional groups under standardized conditions(tetrahydrofuran, $0{\circ}$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of STDEA was also compared with those of the parent sodium aluminum hydride (SAH) and lithium tris(diethylamino)aluminum hydride (LTDEA). The reagent appears to be milder than LTDEA. Nevertheless, the reducing action of STDEA is very similar to that observed previously for LTDEA, as is the case of the corresponding parent sodium and lithium aluminum hydrides. STDEA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and 1-hexanol evolved hydrogen slowly, whereas 3-hexanol and 3-ethyl-3-pentanol, secondary and tertiary alcohols, were essentially inert to STDEA. Primary amine, such as n-hexylamine, evolved only 1 equivalent of hydrogen slowly. On the other hand, thiols examined were absolutely stable. STDEA reduced aidehydes and ketones rapidly to the corresponding alcohols. The stereoselectivity in the reduction of cyclic ketones by STDEA was similar to that by LTDEA. Quinones, such as p-benzoquinone and anthraquinone, were reduced to the corresponding 1,4-dihydroxycyclohexadienes without evolution of hydrogen. Carboxylic acids and anhydrides were reduced very slowly, whereas acid chlorides were reduced to the corresponding alcohols readily. Esters and epoxides were also reduced readily. Primary carboxamides consumed hydrides for reduction slowly with concurrent hydrogen evolution, but tertiary amides were readily reduced to the corresponding tertiary amines. The rate of reduction of aromatic nitriles was much faster than that of aliphatic nitriles. Nitrogen compounds examined were also reduced slowly. Finally, disulfide, sulfoxide, sulfone, and cyclohexyl tosylate were readily reduced without evolution of hydrogen. In addition to that, the reagent appears to be an excellent partial reducing agent: like LTDEA, STDEA converted ester and primary carboxamides to the corresponding aldehydes in good yields. Furthermore, the reagent reduced aromatic nitriles to the corresponding aldehydes chemoselectively in the presence of aliphatic nitriles. Consequently, STDEA can replace LTDEA effectively, with a higher selectivity, in most organic reductions.

• Journal of Microbiology and Biotechnology
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• v.18 no.4
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• pp.663-669
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• 2008

The solvent-tolerant bacterium Enterobacter sp. VKGH12 is capable of utilizing n-butanol and contains an $NAD^+$-dependent n-butanol dehydrogenase (BDH). The BDH from n-butanol-grown Enterobacter sp. was purified from a cell-free extract (soluble fraction) to near homogeneity using a 3-step procedure. The BDH was purified 15.37-fold with a recovery of only 10.51, and the molecular mass estimated to be 38 kDa. The apparent Michaelis-Menten constant ($K_m$) for the BDH was found to be 4 mM with respect to n-butanol. The BDH also had a broad range of substrate specificity, including primary alcohols, secondary alcohols, and aromatic alcohols, and exhibited an optimal activity at pH 9.0 and $40^{\circ}C$. Among the metal ions studied, $Mg^{2+}$ and $Mn^{2+}$ had no effect, whereas $Cu^{2+},\;Zn^{2+}$, and $Fe^{2+}$ at 1 mM completely inhibited the BDH activity. The BDH activity was not inhibited by PMSF, suggesting that serine is not involved in the catalytic site. The known metal ion chelator EDTA had no effect on the BDH activity. Thus, in addition to its physiological significance, some features of the enzyme, such as its activity at an alkaline pH and broad range of substrate specificity, including primary and secondary alcohols, are attractive for application to the enzymatic conversion of alcohols.

• Journal of Photoscience
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• v.10 no.2
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• pp.181-184
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• 2003

Photochemical reactions of some organic molecules on titanium dioxide were investigated in methanol. A methanolic solution of trans-cinnamic acid and titanium dioxide was irradiated with 300 nm UV lamps for 24 h to afford methyl cinnamate. In the case of trans-cinnamamide, the major product was found to be 3-phenylpropionamide, i.e., a saturation product of ethylenic double bond. However, irradiation of urocanic acid, caffeic acid, ethyl cinnamate, trans-chalcone, trans-cinnamonitrile, trans-stilbene or trans, trans-1,4-diphenyl-1,3-butadiene on titanium dioxide under the same conditions did not give any noticeable products. Meanwhile, when irradiated some aromatic aldehydes, such as trans-cinnamaldehyde, l-naphthaldehyde, and 2-naphthaldehyde in methanol, vicinal diols and alcohols derived from the diols were produced. On the other hand, irradiation of 9-anthraldehyde and titanium dioxide in methanol afforded only alcohols, in which diol was not observed.

• Fisheries and Aquatic Sciences
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• v.17 no.2
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• pp.189-195
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• 2014

Headspace volatile compounds of cold-stored and freeze-dried Krill Eupausia superba were analyzed to investigate their flavor qualities using a system combining a dynamic headspace isolator, an automatic thermal desorber, and a gas chromatograph-mass-selective detector. Levels of oxidation products of polyunsaturated fatty acids such as aldehydes, alcohols, and ketones, which are known to give seafood a nasty smell because of their low flavor threshold values, increased during cold storage of krill. Notably, levels of 2-methylpropanal, 3-methylbutanal, 2-methylbutanal and 2-butanone increased during its storage. They can be considered index compounds of off-odor according to freshness degradation during storage. By contrast, in freeze-dried krill powder, levels of aldehydes, ketones, and aromatic compounds decreased rapidly. Only alcohols, which did not greatly affect the food flavor, were isolated in large amounts. It was confirmed that levels of oxidized compounds of krill increased during cold storage, but decreased in freeze-dried krill.

• Journal of the Korean Society of Industry Convergence
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• v.12 no.3
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• pp.143-147
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• 2009

The enantioselective reduction of representative prochiral alkyl-aryl ketones with a new chiral alkoxy-amine-aluminum derivatives from aluminum hydride and ${\alpha},{\alpha}$-diphenyl-${\beta}$-amino alcohols, such as (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol(AMDPB) and (S)-(-)-2-(diphenylhydroxy-methyl)pyrrolidine(DPHMP), in THF at $0^{\circ}C$ was studied. In the reduction of alkoxy-amine-aluminum derivatives, acetophenone, propiophenone, isopropiophenone, and butyrophenone are reduced to corresponding aromatic secoundary alcohols with 34~60 % enantiomeric excess of (S)-isomers. For such ketones, the optical induction was enhanced by increasing a size of alkyl groups.

• Bulletin of the Korean Chemical Society
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• v.10 no.1
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• pp.12-15
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• 1989

Various tertiary amides have been subjected to the reduction by borane-THF in the presence of trimethyl borate at $0^{\circ}C$ and the product ratio of alcohol and amine have been analyzed in order to find out the possible way to obtain one product exclusively on the basis of the structure of amides. In the case of N,N-dimethyl derivatives of both linear aliphatic and aromatic amides the corresponding alcohols were produced predominantly. However, the bulkier tertiary amides such as N,N-diethyl and hindered acid derivatives afforded amines rather than alcohols. The mechanism of borane reduction of tertiary amides is also discussed.

• Archives of Pharmacal Research
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• v.21 no.6
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• pp.723-728
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• 1998

The chemical behaviours of 4-methyl-2-oxo-2H-benzopyran-7-yl oxoacetyl hydrazine (2) towards some different reagents such as anhydride compounds, aromatic aldehydes, carb on disulphide, and nitrous acid yielded the corresponding pathalazine derivatives (3, 4, 5), hydrazone derivative (6), 1,3,4-oxadiazole derivative (7, 8, 9) and acid azide (10) respectively. Treatmen of 10 with absolute alcohols, amines and ethyl amino acid ester gave the corresponding carbamate derivative (11), substituted urea derivative (12) and ethyl substituted alkyl acetate (13) respectively. The biological activity of some synthesized compounds was evaluated.