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Antioxidant Effect of Tocopherols and Tocotrienols and cis/trans-, trans/trans-Hydroperoxide Isomer from Linoleic Acid Methylester (토코페롤류의 항산화작용과 Linoleic Acid Methylester에서 생성된 cis/trans-, trans/trans-Hydroperoxide Isomer)

  • Lee, Hyung-Ok
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.307-312
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    • 1993
  • Antioxdant effect was studied in model system with linoleic acid methylester and tocochromanols $({\alpha}-,\;{\beta}-,\;{\gamma}-,\;{\delta}-tocopherol\;and \;{\alpha}-,\;{\gamma}-,\;{\delta}-tocotrienol)$ under definite autoxidation condition-temperature $(40,\;60,\;80^{\circ}C),\;O_2\;(0,\;10,\;20%\;O_2\;in\;N_2)$. 13-Hydroperoxy-9-cis-11-trans-, 13-hydroperoxy-9-trans-11-trans-, 9-hydroperoxy-10-trans-12-cis-, 9-hydroperoxy-10-trans-12-trans-octadecadienoic acid methylester as the major oxidation product were produced from linoleic acid methylester by autoxidation, analyzed with HPLC and antioxidant activities were compared by their quantitative changes. Experimental results showed that all added tocochromanols except ${\alpha}-tocotrienol$ had antioxidant effect at $60^{\circ}C$, and also ${\alpha}-tocopherol$, ${\alpha}-tocotrienol$ and ${\delta}-tocotrienol$ had prooxidant effect at $80^{\circ}C$. And cis/trans-hydroperoxide was predominantly produced at $40^{\circ}C$, but trans/trans-hydroperoxide at $80^{\circ}C$. Except no reproductive experimental data in produced hydroperoxides amount, the production ratio of cis/trans-:trans/trans-hydroperoxides in the autoxidation condition of range from $40^{\circ}C/10%,\;O_2\;to\;60^{\circ}C/20%\;O_2$ were as follows: ${\alpha}-T>{\alpha}-T_3>{\gamma}-T>{\beta}-T>{\gamma}-T_3>{\delta}-T>{\delta}-T_3$. This result showed that ${\alpha}-tocopherol$ among tocochromanols had the lowest antioxidant effect.

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Gas Chromatographic Method for Analysis of Fatty Acids in Milk Fat with a Single Injection

  • Hwang, Keum-Taek;Shin, Min-Kyeong
    • Preventive Nutrition and Food Science
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    • v.11 no.3
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    • pp.253-256
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    • 2006
  • The purpose of this study was to develop a gas chromatographic (GC) method to analyze fatty acids in milk fat with a single injection. The single-injection GC method we developed for analyzing fatty acid composition can separate a wide range of fatty acid methyl esters from butyric acid to docosahexaenoic acid. It separated 6 isomers of 18:1 (cis-6, cis-9, cis-11, trans-6, trans-9 and trans-11), 4 isomers of 18:2 (cis-9-cis-12, trans-9-trans-12, cis-9-trans-12 and trans-9-cis-12), and 4 isomers of conjugated 18:2 (cis-9- trans-11, trans-9-cis-11, cis-10-trans-12 and trans-10-cis-12).

Antioxidative Effectiveness and Oxidized Products in Mixture of Methyl Linoleate and Phenolic Compounds (Methyl Linoleate에 대한 Phenol성 물질의 항산화성과 산화 생성물)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.379-385
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    • 1993
  • Antioxidative effectiveness and oxidized products in mixture of methyl linoleate(ML) and phenolic compounds were investigated under oxygen blowing at $37^{\circ}C$ for 9 days. Caffeic acid (3,4-dihydroxy cinnamate ; CML) and phloroglucinol(1,3,5-trihydroxy benzene ; PML) showed higher antioxidative effectiveness for methyl linoleate than 0.05% ${\alpha}-tocopherol$ (TML). Oxidized products in ML group were methyl 8-(2-furyl)-octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In CML group the oxidized products were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer and 9-trans, trans hydroperoxide isomer, but 13-hydroxy isomer was not identified. It was shown that CML were oxidized more slowly than ML group and at 6th day of oxidation, caffeic quinone was found to be major oxidized product of caffeic acid. Oxidixed Products in PML group were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer, and 9-trans, trans hydroperoxide isomer but phloroglucinol was not oxidized even at the 9th day of reaction.

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$TiO_2$-Mediated Photoreactions of Cinnamic Acid and Related Compounds in Methanol

  • Kim, Sung-Sik;Kim, Hyun-Jin;Lee, Hye-Jong;Park, Sang-Kyu
    • 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.

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Microbial Metabolism of trans-2-Dodecenal

  • Kim, Hyun-Jung;Park, Hae-Suk;Lee, Ik-Soo
    • Natural Product Sciences
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    • v.17 no.1
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    • pp.19-22
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    • 2011
  • Microbial metabolism of trans-2-dodecenal (1) was studied. Screening studies have revealed a number of microorganisms that are capable of metabolizing trans-2-dodecenal (1). Scale-up fermentation with Penicillium chrysogenum resulted in the production of two microbial metabolites. These metabolites were identified using spectroscopic methods as trans-2-dodecenol (2) and trans-3-dodecenoic acid (3).

cis-trans Isomeric and Substituent Effects on the Lanthanide Induced Shifts in 2-Phenylcyclopropanic System

  • So, Jung-Ho;Cho, Nam-Sook
    • Bulletin of the Korean Chemical Society
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    • v.5 no.6
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    • pp.226-230
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    • 1984
  • LIS's of cis and trans-methyl-2-phenylcyclopropanecarboxylate, cis and trans-t-butyl-2-phenylcyclopropanecarboxylate, cis and trans-N,N-dimethylcyclopropanecarboxamide, trans-2-phenylcyclopropyl methyl ketone and trans-2-phenylcyclopropyl t-butyl ketone have been studied. The LIS's hold the McConnell-Robertson relation and are mainly influenced by the steric effect. LIS's of trans isomers are larger than those of cis isomers. In trans isomers, the LIS's decrease in the following order: methyl ketone > methyl ester > N,N-dimethyl amide > t-butyl ketone${\sim}$t-butyl ester.

Pressure Effect on the Aquation of $trans-[Cr(tmd)_2F_2]^+\;and\;trans-[Cr(tmd)_2FCl]^+$ Ions ($trans-[Cr(tmd)_2F_2]^+$$trans-[Cr(tmd)_2FCl]^+$ 착이온의 수화반응에 미치는 압력의 영향)

  • Jong-Jae Chung;Han-Tae Kim;Sung-Oh Bek
    • Journal of the Korean Chemical Society
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    • v.33 no.2
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    • pp.164-167
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    • 1989
  • The rate for the aquation of $trans-[Cr(tmd)_2FX]^+(X=F^-,\;Cl^-)$ ion in aqueous acidic solution has been measured by spectrophotometric method at various temperatures and pressures. The rate constants are increased with increasing temperatures and pressures. The values of activation entropy are 5.2 eu for $trans-[Cr(tmd)_2F_2]^+$ and -16.62 eu for $trans-[Cr(tmd)_2FCl]^+$ ions. Activation volumes have all negative values and lie in the limited range $-3∼-2\;cm^3mol^{-1}$ for $trans-[Cr(tmd)_2F_2]^+$ and $-8∼-7\;cm^3mol^{-1} for $trans-[Cr(tmd)_2FCl]^+$ ion. From the above results, we may deduce that the mechanism for the aquation of $trans-[Cr(tmd)_2F_2]^+$ and $trans-[Cr(tmd)_2FCl]^+$ ions is interchange-associative mechanism and dissociative mechanism respectively.

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Biotransformation of trans,trans-farnesol by Wood Rot Fungi (목재부후균에 의한 trans,trans-farnesol의 생물변환)

  • Kim, Young-Hun;Lee, Su-Yeon;Park, Mi-Jin;Choi, In-Gyu;Lee, Jae-Won
    • Korean Journal of Microbiology
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    • v.48 no.1
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    • pp.37-41
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    • 2012
  • In this study, we screened and evaluated possibility of wood rot fungi as biocatalyst for biotransformation of sesquiterpenes. Screening were performed to select the most promising microorganisms with ability to biotransformation the substrate trans,trans-fanesol. Trans,trans-farnesol which is synthesized precursor of sesquiterpenes was used for resistance test on 19 of wood rot fungi. From the 19 tested wood rot fungi, 5 were selected by resistance test on different concentration of trans,trans-fanesol. Biotransformation was performed with selected wood rot fungi on liquid culture. The metabolites detected by GC-MS analysis were nerolidol for Laetiporus sulphureus var. miniatus (jungh) Imaz and eicosane for Coriolus versicolor (L.Fr) Prlar and isoborneol for Fomitopsis pinicola and isocyclocitral for Lampteromyces japonicas. As the results, wood rot fungi could be potential biocatalyst for biotransformation of sesquiterpenes.

Preparation of a Large Quantity of CIS-9, trans-11 and trans-10, cis-12 Conjugated Linoleic Acid(CLA) Isomers from SYnthetic CLA

  • Kim, Seck-Jong;Park, Kyung-Ah;Park, Jung-H.Y.;Kim, Jeong-Ok;Ha, Yeong-Lae
    • Preventive Nutrition and Food Science
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    • v.5 no.2
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    • pp.86-92
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    • 2000
  • Conjugated linoleic acid(CLA) refers to a collective term of positional and geometric isomers of linoleic acid, which are different in their biological activities. The predominant isomer of CLA in animal tissues is cis-9, trans-11; smaller amounts of trans-10, cis-12 CLA isomers, CLA methyl ester (CLA-ME) was chemically syn-thesized from linoleic acid by the alkaline isomerization method. The synthetic CLA-ME, mainly composed of cis-9, trans-11 CLA and trans-10, cis-12 CLA, was dissolved in acetone, stored at 68$^{\circ}C$ for 1 day, and the supernatant(cis-9, trans-11 CLA-Me) was separated from the precipitate (trans-10, cis-12 CLA-Me). After the processes were repeated three times at -68$^{\circ}C$, the whole processes were repeated three times at -71$^{\circ}C$ in order to increase the purity of these two isomers. The cis-9, trans-11 CLA-Me and trans-10, cis-12 CLA isomers were further purified by the urea adduct. Purities of the cis-9, trans-11 CLA-Me and trans-10, cis-12 CLA-Me were 90.3 and 99.9%, respec-tively. This method could be employed for the preparation of a large quantity of highly purified cis-9, trans-11 CLA-Me or trans-10, cis-12 CLA-Me from synthetic CLA-Me.

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Comparison of the Bakery Products Made Commercial Fat or Low Trans Fat (일반 고체지와 저트랜스 고체지를 이용한 베이커리 제품의 특성 비교)

  • Hwang, Pu-Yeon;Kim, Yu-Mi;Lee, Ki-Teak
    • Journal of the East Asian Society of Dietary Life
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    • v.17 no.1
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    • pp.64-71
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    • 2007
  • Breads and cookies made with conventional or low-trans fat(margarine and shortening) were analyzed by determining their trans fat content, textural properties and color values after production. The trans fatty acids content in conventional margarine was three times higher than that of low-trans margarine. Moreover, the content of trans fatty acids in the conventional shortening was 49 times higher than that of low-trans shortening. The trans fatty acid contents of cookies and breads made with low-trans fat, can be reduced more than 2 to 75 times compared to cookies and breads made with conventional fat. In the produced cookies and breads, the color values and textural properties(hardness, springiness, cohesiveness, gumminess and chewiness) did not differ significantly when the conventional fat or low-trans fat was used.

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