• Bulletin of the Korean Chemical Society
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• v.23 no.1
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• pp.65-70
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• 2002

We have evaluated the specific hydroxyl group-solvent and carbonyl group-solvent interactions by using an Alltima C18 stationary phase and by measuring the retention data of carefully selected solutes in 60/40, 70/30, and 80/20(v/v%) acetonitrile/water eluents at 25, 30, 35, 40, 45, and 50 oC. The selected solutes are phenol, acetophenone, alkylbenznes(benzene to hexylbenznene), 4 positional isomers of phenylbutanol, 5-phenyl-1-pentanol, 3 positional isomers of alkylarylketone derived from butylbenzene, and 1-phenyl-2-hexanone. The magnitudes of hydroxyl group-acetonitrile/water specific interaction enthalpies are larger than those of carbonyl group-acetonitrile/water specific interaction enthalpies in general while the magnitudes of carbonyl group-methanol/water specific interaction enthalpies are larger than those of hydroxyl group-methanol/water specific interactions. We observed clear discrepancies in functional group-solvent specific interaction among positional isomers. The variation trends of solute transfer enthalpies and entropies with mobile phase composition in the acetonitrile/water system are much different from those in the methanol/water system. The well-known pocket formation of acetonitrile in aqueous acetonitrile mixtures has proven to be useful to explain such phenomena.

• Bulletin of the Korean Chemical Society
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• v.22 no.4
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• pp.409-412
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• 2001

Poly(p-tert-butyltrimethoxymonopropyloxycalix[4]arene-methylsiloxane) (TBCX-MS) has been prepared and used as a stationary phase in isothermal capillary gas chromatographic separation of some positional isomers. Retention factors (k) and separatio n factors $(\alpha)$ for the isomers were measured and compared with those on poly(p-tert-butyl-dimethoxydipropyloxycalix[4]arene-tetramethyldisiloxane) (TBCX-TMDS), poly(dimethoxydipropyloxycalix[4]arenetetramethyl-disiloxane) (CX-TMDS). Most of the isomers investigated are well resolved on TBCX-MS. Retention of all the compounds decreases on the three phases in the order, TBCX-TMDS ${\geq}$ TBCX-MS > CX-TMDS. Similar retention values on TBCX-TMDS and TBCX-MS seem to indicate that retention property of the two phases is not significantly affected by the spatial position of the calixarene moiety.

• Bulletin of the Korean Chemical Society
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• v.26 no.8
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• pp.1246-1250
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• 2005

We have evaluated the hydroxyl group-solvent specific interactions by using a Lichrosorb RP18 stationary phase and by measuring the retention data of carefully selected solutes in 50/50, 60/40, 70/30, 80/20, and 90/10(v/v%) methanol/water eluents at 25, 30, 35, 40, 45, and 50 ${^{\circ}C}$. The selected solutes are 3 positional isomers of phenylpropanol, that is, 1-phenyl-1-propanol, 1-phenyl-2-propanol, and 3-phenyl-1-propanol. There exist clear discrepancies in ${\Delta}H^o$ (solute transfer enthalpy from the mobile to the stationary phase) and $T{\Delta}S^o$ (solute transfer entropy) among positional isomers. The difference in ${\Delta}H^o$ and $T{\Delta}S^o$ between secondary alcohols (1-phenyl-1-propanol and 1-phenyl-2-propanol)is negligible compared to the difference between the primary alcohol (1-phenyl-3-propanol) and secondary alcohols. The $T{\Delta}S^o$ values of 3-phenyl-1-propanol are close to those of butylbenzene while the $T{\Delta}S^o$ values of secondary alcohols are close to those of propylbenzene. The difference in ${\Delta}{\Delta}H^o$ (specific solute-mobile phase interaction enthalpy) between the primary alcohol and the secondary alcohol decreases with increase of methanol content in the mobile phase. A unique observation is an extremum for 1-phenyl-3-propanol in the plot of $T{\Delta}{\Delta}S^o$ vs. methanol volume %. The positive sign of $T{\Delta}{\Delta}S^o$ of 3-phenyl-1-propanol implies that the entropy of 3-phenyl-1-propanol is greater than that of the hypothetical alkylbenzene (the same size and shape as phenylpropanol) in the mobile phase.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.300.1-300.1
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• 2003

Salmon calcitonin (sCT) is a therapeutic polypeptide hormone consisting of 32 amino acids (3432 Da). As with other bioactive peptide therapeutics, however, therapeutic use of sCT has been limited due to the problems of short circulating half-life and rapid proteolytic degradation. To get over this problem, the three positional isomers of mono-PEGylated sCT were prepared and among these, the best drug candiate for nasal application was chosen. (omitted)

• Asian-Australasian Journal of Animal Sciences
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• v.17 no.9
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• pp.1315-1328
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• 2004

Conjugated linoleic acid (CLA) is a mixture of positional and geometric isomers of octadecadienoic acid with two conjugated double bonds. Of more than a dozen isomers of CLA found naturally in dairy and meat products from ruminants, c-9, t-11 and t-10, c-12 are the two isomers with known physiological importance, including anticarcinogenic, antidiabetic, antilipogenic, and antiatherosclerotic effects. Positive effects of CLA on immune function and bone modeling have also been reported. In spite of the compelling findings in tissue cultures and experimental animal models, its effect, dose, and mechanism of action vis-à-vis specific isomers remains speculative. Results obtained from animal models are inconclusive and conflicting at times in humans, where the research data is limited. It appears that there is a long way to go before CLA could be accepted unequivocally as having definite effects in any or all of these physiological states and how such effects actually occur in humans. The objective of this review is to critically examine the available literature on potential health benefits of CLA observed in cell culture, animal models, and human subjects, wherever possible and to a certain extent the mechanism of action associated with these biological activities.

• Biotechnology and Bioprocess Engineering:BBE
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• v.11 no.6
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• pp.477-483
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• 2006

Ionic liquids in the form of organic salts are being widely used as new solvent media. In this paper three positional isomers, o-amino benzoic acid, m-amino benzoic acid, and p-amino benzoic acids were separated with four different ionic liquids as mobile phase additives using high performance liquid chromatography (HPLC). The following ionic liquids were used: 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIm][$BF_{4}$]), 1-ethyl-3-methylimidazolium tetrafluoroborate ([EMIm][$BF_{4}$]), 1-ethyl-3-methylimidazolium methylsulfate ([EMIm][MS]), and 1-octyl-3-methylimidazolium methylsulfate ([OMIm][MS]). The effects of the alkyl group length on the imidazolium ring and its counterion, and the concentrations of the ionic liquids on the retention factors and resolutions of amino benzoic acid isomers were tested. The results of the separations with ionic liquids as the eluents were better than those without ionic liquids. Excellent separations of the three isomers were achieved using 2.0-8.0 mM/L [OMIm][MS] and 1.0-8.0 mM/L [EMIm][MS] as the eluent modifiers.

• Korean Journal of Food Science and Technology
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• v.28 no.3
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• pp.440-445
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• 1996

An attempt was made to study the relative composition of Monohydroperoxide isomers of methyl linoleate oxidized to different peroxide values at 60, 90, 120 and $150^{\circ}C$, respectively. HPLC was used to analyze and isolate the monohydroperoxide isomers fractionated by silica gel column after reduction with NaBH.. GC-MS was used to identify four monnhydroperoxide isomers as trimethylsilyl (TMS) in mixtures of oxidized methyl linoleate In the geometrical isomers, the proportions of 9/13-OOH-trans, trant-diene were higher than those of 9/13-OOH-cis, trans-diene at $60^{\circ}C$ and $90^{\circ}C$. However in the initial stage at $150^{\circ}C$, the proportions of 9/13-OOH-cis, trans-diene were slightly higher than those of 9/13-OOH-trans, trans-diene. In case of positional isomers, equal proportions of 9-OOH-10, 12-diene and 13-OOH-9, 11-diene were found in all samples of methyl linoleate oxidized at different temperatures and peroxide levels.

• 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.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.30 no.3
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• pp.355-360
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• 1997

In order to investigate the influence of photosensitized oxidation in the sun-dried irish moss (Chondrus Ocellatus), laver (Porphyra Yezoensis) and ultra violet irradiated oyster (Crassostrea gigas) the oxidation of lipid and isomers of hydroperoxides were analyzed by gas chromatography-mass spectrometry. The lipid contents of oyster, irish moss and layer were $2.7\%,\;0.1\%,\;0.1\%$ of respectively. Peroxide value, 56,7 meq/kg in the raw oyster was increased of 100.9 meq/kg by the U.V, irradiation for 4 hours. Also the peroxide values of the irish moss and laver were increased by the sun-drying. In the identification of hydroperoxides isomers by trimethylsily (TMS) derivative of photo-oxidized lipid from oyster, irish moss and laver, the proportions of positional isomer, 9-OOH and 13-OOH were dominant than those 10-OOH and 12-OOH.

• Journal of Life Science
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• v.27 no.8
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• pp.965-973
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• 2017

Conjugated linoleic acid (CLA) is a group of positional and geometric isomers of linoleic acid with conjugated double bonds at C9,C11 and C10,C12 positions. Of possible CLA isomers, a naturally occurring CLA isomer is c9,t11-CLA which is produced from linoleic acid by linoleate isomerase from various rumen and lactic bacteria, and mushroom mycelia. Meanwhile, synthetically prepared CLA contained an equal amount of c9,t11-CLA and t10,c12-CLA isomers, and other isomers as minor constituents. CLA was firstly mentioned in 1939 during the elaidinization reaction of linoleic acid. Thereafter, CLA was not an attractant to scientists because it was not scientifically interested any more. However, since the anticarcinogenic action was driven from 7,12-dimethylbenz[a]anthracene (DMBA)-induced mouse skin carcinogenesis in 1987, CLA-related researches were drastically elevated, resulting in approximately 6,100 research papers in literature, so far. CLA exhibited the significant biological activities: anticarcinogenic, antidiabetic, antihypertensive, antiatherosclerotic, body-fat reducing, antioxidative, antiinflammatory, testosterone producing and other activities. Interestingly, two major CLA isomers, c9,t11-CLA and t10,c12-CLA, exhibited different biological activities. Meanwhile, t,t-CLA isomers which is minor constituent of chemically synthesized CLA from linoleic acid exhibited more potent anticarcinogenic activity in carcinogen-induced animal models and cancer cell lines than other CLA isomrs. In the present review, the significant biological activities of CLA were discussed along with historical studies of CLA since 1939.