• Food Science and Biotechnology
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• v.17 no.5
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• pp.1032-1037
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• 2008

Lowly volatile heterocyclic sulfur compounds generated in autoclaved garlic extract were isolated and identified, and their antimicrobial activity was determined. Two kinds of unusual volatile sulfur compounds were separated from heated garlic by preparative recycling high performance liquid chromatography (HPLC), and identified by gas chromatography (GC)-mass spectrometry (MS) and $^1H$-nuclear magnetic resonance (NMR). They had heterocyclic structures with 4 to 5 sulfur atoms in the molecules. 4-Methyl-1,2,3-trithiolane (MTTT) is highly volatile and was not able to be concentrated, and was identified by GCMS only. MTTT and 6-methyl-1,2,3,4,5-pentathiepane (MPTP) are lowly volatile and were obtained in pure states to be positively identified for the first time. All 3 heterocyclic sulfur compounds began to appear by the time when the early-formed diallyl sulfides started to disappear. The minimum inhibitory concentration range of MTTT and MPTP was determined to be between 1 and 6 ppm against all yeasts tested. MTTT and MPTP were lowly volatile and sparingly soluble in water.

• Tribology and Lubricants
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• v.16 no.5
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• pp.332-340
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• 2000

The reduction of sulfur content in the diesel fuel has caused the poor lubricity of diesel fuel in the distributor type injection pumps of diesel engines that use the diesel for lubrication of their moving parts. To investigate the reason for poor lubricity of low sulfur diesel fuels, the wear scar diameters by HFRR (High Frequency Reciprocating Rig) were measured on the diesel fuels from Korean markets and the results were compared with their physical and chemical properties. Also, the lubricity change and the improvement effects on lubricity additives for the ultra low sulfur diesel fuel, were made experimentally, that will be regulated to a maximum of 0.005 wt% from about 2005 were evaluated. As a result, a good correlation was found between the wear scar diameter and the polyaromatic compound which includes heterocyclic compound in the diesel fuel. It was also found that the content of polyaromatic compound including heterocyclic compound was affected by the amount of desulfurization treatment fraction. And the lubricity additives with ester base were more effective than that with acid base on the ultra low sulfur diesel fuel. Therefore, it is suggested that the factors affecting the lubricity stated above should be taken into account to improve the lubricity property of the diesel fuel in the refining process.

• Food Science and Biotechnology
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• v.18 no.3
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• pp.771-775
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• 2009

Antimicrobial activity of garlic (pH 6.0) heated at $120^{\circ}C$ reached its maximum at 45 min of heating and maintained the level for the rest of heating time (300 min) when tested against Candida utilis ATCC42416. The principal antimicrobial compound was allyl alcohol (AA), a highly volatile compound without sulfur in its molecule. The concentration of AA in heated garlic gradually increased to over 2,000 ppm for the first 90 min and stayed at the level without appreciable changes in spite of further heating. Other antimicrobial compounds secondary to AA were lowly volatile sulfur compounds including diallyl polysulfides (diallyl trisulfide, diallyl tetrasulfide, and diallyl pentasulfide) and heterocyclic sulfur compounds (4-methyl-1,2,3-trithiolane, 5-methyl-1,2,3,4-tetrathiane, and 6-methyl-1,2,3,4,5-pentathiepane). When the pH of the garlic extract was lowered before heating, considerably more secondary antimicrobial sulfur compounds were formed and the antimicrobial activity was stronger than the pH unadjusted garlic. Lowly volatile sulfur compounds contributed a significant part of antimicrobial activity of heated garlic only during the early period (45-120 min) of heating regardless of pH treatment.

• Bulletin of the Korean Chemical Society
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• v.18 no.5
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• pp.484-488
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• 1997

The angular and planar heterocyclic compounds containing nitrogen, sulfur and oxygen were synthesized by reaction of 6,7-dichloro-5,8-quinoxalinedione with aromatic and aliphatic dinucleophiles. Nucleophilic reactivity was somewhat different between 2,3-dichloro-1,4-naphthoquinone and 6,7-dichloro-5,8-quinolinedione with dinucleophiles. The distribution of electron in heterocycle appeared to contribute to this difference. The intercalation comple of planar heterocyclic compound between GC/GC base pairs showed the optimum intercalation but the intercalation of angular heterocyclic compound was not good. Thus, the planar compound was expected to have antitumor activity.

• Journal of the Korean Society of Food Science and Nutrition
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• v.30 no.6
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• pp.1033-1037
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• 2001

Garlic oleoresins were made by extracting with four solvents of methanol, methyl acetate hexane and acetone from chopped garlic, respectively, and the volatile compounds of each extract were separated by gas chromatography installed with polar (supelcowax-10$^{TM}$) and nonpolar (HP-5) capillary columns, respectively, and identified by matching mass data of mass selective detector and Kovat\`s retention index with references. The numbers of the volatile compounds identified the garlic oleoresin by polar and nonpolar columns from in garlic oleoresins were 41 and 32, respectively. In polar column, 13 pyrans, 11 sulfur-containing compounds 6 furans 2 alcohols and 2 heterocyclic compounds were identified. In nonpolar column, 11 sulfur-containing compounds 5 acids 3 furans and eugenol were identified. The major sulfur-containing compounds identified from the oleoresins were 3, 3'-thiobis-1-propene, methyl 2-propenyl disulfide, dimethyl trisulfide, di-2-prnpenyl-trisulfide, 2-thiophenecarboxylic acid. The amount of these sulfur-containing compounds isolated from the oleresins were more abundant in polar column than in nonpolar column. The most efficient solvent for extracting volatile compounds of garlic was methanol but the most useful solvent for extracting sulfur-containing compounds was methyl acetate of less polarity.y.

• Food Science and Biotechnology
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• v.18 no.1
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• pp.66-72
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• 2009

An aqueous ribose-cysteine model system (initial pH 5.6) was conventionally heated to the same browning at varying temperatures ($120-180^{\circ}C$), supercritical carbon dioxide (SC-$CO_2$, 20 MPa) was also applied on the same matrices for same periods at each temperature and about 20% reduction of the absorbance at 420 nm was observed as compared with sole thermal treatment. The headspace volatiles from Maillard reaction mixtures were analyzed by solid-phase microextraction (SPME) in combination with gas chromatography and mass spectrometry (GC-MS), and predominated with sulfur containing compounds, such as thienothiophenes, polysulfur alicyclics, thiols, and disulfides. Reaction temperature exhibited complex effects on volatiles formation and those effects became further complicated by the SC-$CO_2$ treatment. The formation of noncarbonyl polysulfur heterocyclic compounds and thienothiophenes was generally favored at high temperatures. Most volatiles were inhibited in SC-$CO_2$ as compared with thermal treatment alone, however, the well-known meaty aromatic compounds, such as thiols and disulfides, were obviously enhanced.

• The Journal of the Convergence on Culture Technology
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• v.9 no.4
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• pp.503-508
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• 2023

Tryptane derivatives are substances that treat acute migraines, and many studies have been conducted on analysis methods such as chromatography, electrochemistry, spectroscopy, and capillary electrophysiology. Recently, analytical chemists have become more interested in drug analysis and solving fundamental problems of biological importance. Therefore, in this study, the chemical properties of each derivative were investigated by calculating the total energy, band gap, electrostatic potential, and charge of Sumatriptan, Lizatriptan, Naratriptan, and Eletriptan using HyperChem8.0's semi-empirical PM3 method. As a result of this study, in the case of Sumatriptan, Naratriptan, and Eletriptan, chemical reactions are expected to proceed centering on oxygen and nitrogen atoms bonded to sulfur atoms. In addition, in the case of Rizatriptan without a sulfur atom, it was shown that the chemical reaction proceeds at the 17th and 19th nitrogens of the 5-membered heterocyclic compound.