JSCS Vol 67, No. 1  

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J. Serb. Chem. Soc. 67(1) 1–6 (2002)
UDC 546.56+546.47:66.061+620.168.3
JSCS – 2917
Original scientific paper

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An efficient de novo synthesis of 3’-deoxythymidine from D-xylose

GORDANA CETKOVIC, STEVAN LAJSIC, MIRJANA POPSAVIN*, VELIMIR POPSAVIN* and DUSAN MILJKOVIC*

Department of Applied Chemistry, Faculty of Technology, University of Novi Sad, Bulevar Cara Lazara 1 and
*Institute of Chemistry, Faculty of Science, University of Novi Sad, Trg D. Obradovica 3, YU-21000 Novi Sad, Yugoslavia

(Received 24 April 2001)
An efficient stereospecific synthesis of 3’-deoxythymidine has been achieved, starting from D-xylose. The key step of the synthesis involved the NBS promoted conversion of 5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-ribose diethyl dithioacetal (4) into the 1-O-acetyl-5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-b-D-ribofuranose (5), followed by the stereospecific coupling of the intermediate 5 with silylated thymine, in the presence of ethylaluminium dichloride as the catalyst.

Keywords: 3'-deoxythymidine, dethioacetalization, N-glycosylation, modified nucleosides, D-xylose.


J. Serb. Chem. Soc. 66(10)7–15(2002)
UDC 542.913+66.095.12:577.123
JSCS – 2918
Original scientific paper

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Antioxidant activities of the constituents of Picris echoides

MIRJANA MILOVANOVIC, KSENIJA PICURIC-JOVANOVIC, VERICA DJERMANOVIC* and MILUTIN STEFANOVIC**

Department of Food Technology, Faculty of Agriculture, University of Belgrade, P. O. Box 127, Nemanjina 6, YU-11081 Zemun,
*Institute of Chemistry, Technology and Metallurgy, Center for Chemistry, Njegoseva 12, YU-11000 Belgrade and
**Faculty of Chemistry, Studentski trg 16, P. O. Box 158, YU-11001 Belgrade, Yugoslavia

(Received 22 June 2001)
Some flavonoids with antioxidant properties from the aerial parts of the plant species Picris echoides (family Asteraceae) were identified. Upon chromatography, the ethyl acetate extract afforded flavonoids, such as: flavone apigenin (1) and its glucoside, cosmosiin (2), as well as common plant constituents from this family, flavonol galetin (3, 3,4’,5,6,7-pentahydroxyflavone) and 4,4’,6,7-tetrahydroxyaurone (4). The structure of the aurone 4 has not been described so far in the literature and presented a very rare type of aurone skeleton. The structures of the isolated compounds were determined by interpretation of their physical and spectral data. The antioxidant activities of different extracts from Picris echoides were measured by the Schaal oven test at 60şC and by the Rancimat method at 100şC. Water/ethanol extracts (2:8, v/v), in concentrations of 0.02 and 0.05 %, showed lower activity than commercial tocopherol (Tch). On the contrary, the purified ethyl acetate extracts showed a strong concentration-dependent antioxidant effect. The investigation demonstrated that galetin was the main flavonol from this origin. According to the results of the two methods, galetin (3) showed a two-fold better activity than did Tch and a lower activity than did butylated hydroxyanisole (BHA). The aurone 4 exhibited significantly lower antioxidant activity than did galetin at the same concentration level. Thus, the plant species P. echoides is a new and favorable source of natural lipid antioxidants.

Keywords: Picris echoides, Lactuceae, antioxidant activity, flavonoids.


J.Serb.Chem.Soc. 67(1)17–25(2002)
UDC 547.73:667.644.3+677.494.674
JSCS – 2919
Original scientific paper

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Thiophene based monoazo disperse dyes for polyester fabric

HARI RAGHAV MARADIYA and VITHAL SOMA PATEL*

V. P. and R. P. T. P. Science College Vallabh Vidyanagar 388 120, Gujarat State, India and
*Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat State, India

(Received 4 May 2001)
A series of monoazo disperse dyes have been prepared by coupling 2-amino-3-carbethoxy-4,5-dimethylthiophene with various N-arylmaleimides. The monoazo disperse dyes were characterised by IR spectral studies and elemental analysis. These dyes were applied at 2 % depth on polyester fabrics and gave light yellow to brown colour hues with fair fastness to light and very good to excellent fastness to washing, rubbing, perspiration and sublimation. The percentage exhaustion of the dyebath and fixation on the fabric were found to be very good.

Keywords: 2-amino-3-carbethoxy-4,5-dimethylthiophene, disperse dyes, exhaustion, fixation, polyester, fastness.


J.Serb.Chem.Soc. 67(1)27–30(2002)
UDC 575.825:579.87+543.54
JSCS – 2920
Note

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N O T E
The isolation of (6S, 9S)-cyclo(prolylvalyl) from marine actinomycete, by use of high speed countercurrent chromatography

ANDRIJA SMELCEROVIC, MIRKO SCHIEBEL* and SINISA DJORDJEVIC**

*1Chemical Industry “Nevena”, Djordja Stamekovica b.b., YU-16000 Leskovac, Yugoslavia,
*Department of Organic Chemistry, Tammanstrasse 2, 37077 Göttingen, Germany and
**Faculty of Technology, Bulevar Oslobodjenja 124, YU-16000 Leskovac, Yugoslavia

(Received 3 May, revised 31 July 2001)
The marine actinomycete B 1758 came from the actinomycete collection of the Alfred Wegener Institute for Polar and Marine Research in Bremerhafen, Germany. 1.079 g of raw extract was obtained by fermentation. Seven fractions were separated by column chromatography on silica gel. Fraction 4 was separated by high speed countercurrent chromatography. Fraction 4.6 yielded 5.2 mg of (6S, 9S)-cyclo(prolylvalyl).

Keywords: (6S, 9S)-cyclo(prolylvalyl), marine actinomycete B 1758, HSCCC.


J. Serb. Chem. Soc. 67 (1) 31–39(2002)
UDC66.022.36+631.022.3:547.56
JSCS –2921
Original scientific paper

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The stability of emulsions in the presence of additives

S. GASIC, B. JOVANOVIC* and S. JOVANOVIC*

Institute for Plant Protection and Environment, Teodora Drajzera 9, YU-11000 Belgrade and
*Faculty of Technology and Metallurgy, Karnegijeva 4, YU-11000 Belgrade, Yugoslavia

(Received 26 April, revised 8 August 2001)
The influence of different additives on the effective HLB values of non-ionic emulsifiers was studied by the method of the determination of the phenol index values and by the determination of the emulsion inversion point in the system with xylene as the oil phase. Ethanol, glycerol and ethylene glycol were investigated as additives. The method of the determination of the phenol index value was applied on two homologous series of non-ionic emulsifiers: nonylphenolpolyglycolethers with 10, 15, 23 and 30 moles of bound ethylene oxide and polyglycolethers of fatty alcohols (C16–C18) with 15, 20 and 23 moles of bound ethylene oxide. The additives were applied in the concentration of 5, 10, 15 and 20 %. The results showed that ethanol and ethylene glycol increased the phenol index value. The influence of ethanol was more pronounced. On the contrary, glycerol reduces the phenol index value. There were small differences in the influence of these additives on certain members of both homologous series, but the general trend is presented here. The influence of the same additives on the values of the emulsion inversion point was investigated in the system with xylene and nonylphenolpolyglycolethers with 10 moles of bound ethylene oxide. Ethanol and ethylene glycol were applied in the concentrations of 1, 5, 10 and 15 %, and glycerol in 5,7.5,10 and 15 %. The results showed that ethanol and ethylene glycol reduce the emulsion inversion points, while glycerol increases them. On the basis of these investigations it can be concluded that ethanol and ethylene glycol could contribute to an increase in the stability of emulsions, glycerol has the opposite effect. The results of both applied methods are in accordance.

Keywords: additives, emulsion, phenol index value, emulsion inversion point.


J. Serb. Chem. Soc. 67 (1) 41–51(2002)
UDC 546.56,546.47:66.061+620.168.3
JSCS – 2922
Original scientific paper

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Extraction and separation studies of zinc(II) and copper(II) with D2EHPA and PC-88A from perchlorate media

RAJEEV K. SINGH and PURSHOTTAM M. DHADKE

Department of Chemical Technology, University of Mumbai, Mumbai – 400 019, India

(Received 4 April, revised 17 July 2001)
The extraction behaviours of Zn(II) and Cu(II) from perchlorate media have been investigated using bis-2-ethylhexyl phosphoric acid (D2EHPA) and 2-ethylhexyl phosphoric acid mono-2-ethylhexyl ester, (PC-88A) in toluene. The extraction of Zn(II) was found to be quantitative in the pH range 2.5 to 3.0 and 3.0 to 4.0 using 1.0x10-1 mol dm-3 D2EHPA and 1.0 ´ 10-2 mol dm-3 PC-88A in toluene, respectively, while Cu(II) was extracted quantitatively in the pH range 6.0 to 8.0 and 5.5 to 7.0 with 1.0x10-2 mol dm-3 and 1.0x10-3 mol dm-3 D2EHPA and PC-88A in toluene, respectively. Zn(II) was stripped with 4.0 mol dm-3 HCl, while Cu(II) with 2.0 mol dm-3 H2SO4 and 3.0 mol dm-3 HNO3 from the organic phase containing D2EHPA and PC-88A, respectively. The probable extracted species were ascertained by log D vs. log [HR] plot to be ZnR42HR and CuR2.2HR for both the reagents. These methods were used for the determination of Zn(II) and Cu(II) in real samples. The separation of Zn(II) and Cu(II) were carried out from each other and with associated metals.

Keywords: zinc, copper, D2EHPA, PC-88A, extraction, stripping, separation.


J.Serb.Shem.Soc. 67(1)53–60(2002)
UDC 582.793:54–45+535.342+543.552
JSCS – 2923
Original scientific paper

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The spectroabsorptiometric and voltammetric behavior of malvin in buffered solutions and its antioxidant properties

LJUBISA M. IGNJATOVIC, JASMINA M. DIMITRIC MARKOVIC, DRAGAN A. MARKOVIC and JELISAVETA M. BARANAC

Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12, P. O. Box 137, YU-11000 Belgrade, Yugoslavia

(Received 1 March, revised 18 July 2001)
In the present work the structural transformations of malvin in aqueous acetate buffer solutions were investigated over a wide pH range under in vitro conditions using electronic absorption spectroscopy. In addition to the spectroabsorptiometric investigation, the voltammetric behavior and the mechanism of the redox process of this molecule were studied, in order to define its antioxidant properties. The electronic absorption spectra reveal that the structural changes of malvin, caused by changes in the pH of the medium, lead to changes in the voltammetric behaviour of this molecule. The dependence of the oxidation potential of malvin on pH, which can be explained by the presence of different electroactive molecular structures of malvin at different pH values, indicates different mechanisms of the electrode process. The voltammetric activity of malvin is compared semiquantitatively with the voltammetric activity of a standard synthetic antioxidant, BHA, and a natural antioxidant, quercetin.

Keywords: malvin, UV-VIS spectra, cyclic voltammetry, antioxidant properties.


J.Serb.Chem.Soc. 67(1)61–67(2002)
UDC 621.3.014:531.42:541.135+669.3.62–492.2
JSCS – 2924
Original scientific paper

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The effect of reversing current deposition on the apparent density of electrolytic copper powder

K. I. POPOV, LJ. J. POPOVIC*, E. R. IVANOVIC**, V. RADMILOVIC and M. G. PAVLOVIC**

Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, YU-11000 Belgrade,
*ICTM – Department of Electrochemistry, Njegoseva 12, YU-11000 Belgrade and
**Faculty of Agriculture,University of Belgrade, Nemanjina 6, 11080 Zemun – Belgrade, Yugoslavia

(Received 6 June 2001)
The possibility of depositing copper powders with different apparent density by changing the shape of reversing current wave is shown. The morphology and crystallinity of powder particles can be varied considerably by changing shape of the reversing current wave and, hence, the apparent density of powders. The relation of apparent density with particle morphology and structure was illustrated.

Keywords: reversing current, apparent density, electrolytic copper powder.


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