10.1007/s11172-007-0172-3
The research focuses on the synthesis and antioxidant properties of sodium S-[3-(hydroxyaryl)propyl] thiosulfates and [3-(hydroxyaryl)propane]-1-sulfonates, which are derivatives of spatially hindered phenols. These compounds were synthesized from dialkylphenols through a series of intermediate products, with the aim of creating hydrophilic "hybrid" compounds capable of inhibiting lipid peroxidation in various ways, thus serving as potential antioxidants for biological and medical applications. The experiments involved the oxidation of methyl oleate in aqueous sodium dodecyl sulfate (SDS), where the rate constants of the interaction of the synthesized compounds with lipoperoxide radicals were determined. This model reaction served as a satisfactory model for the oxidation of lipids in biomembranes. The analysis included the determination of the reactivity of the synthesized compounds towards peroxy radicals, which was quantified by the k3/k1 parameter, and was based on the experimentally determined values of the uninhibited oxidation rate (W0) and the inhibited oxidation rate (W). The study also involved the synthesis of various intermediates and final products, which were confirmed by elemental analysis and spectral data, including 1H NMR spectral data. The research was financially supported by the Russian Foundation for Basic Research.
10.1007/BF02518120
The research aimed to optimize the reaction conditions for the synthesis of sorbitol fatty acid polyesters (SFPE), potential fat substitutes, using response surface methodology. The study focused on four parameters: reaction temperature, reaction time, mole ratio of fatty acid methyl esters (FAME) to sorbitol, and mole ratio of fatty acid sodium soaps (FASS) to sorbitol. The chemicals used included sorbitol, methyl oleate, sodium oleate, and potassium carbonate. The research concluded that the optimum conditions for high yield of SFPE were a reaction temperature of 144°C, a reaction time of 6.65 hours, a mole ratio of FAME to sorbitol of 10.7:1, and a mole ratio of FASS to sorbitol of 0.77:1, resulting in an experimental yield close to the predicted value of 94%.
10.1246/cl.1988.1785
This research focuses on the first enantiospecific total synthesis of dimorphecolic acid, a compound with significant biological interest due to its role as a self-defensive substance against rice blast disease and its cation-specific ionophoric activity. The study also describes the synthesis of 5(S)-HETE and 12(S)-HETE, which are important monohydroxylated metabolites of arachidonic acid involved in inflammation and other health issues. The purpose of the research is to provide efficient and stereocontrolled routes for synthesizing these compounds, which are difficult to obtain from natural sources, thereby facilitating further biological investigations. The key chemicals used in the synthesis include methyl oleate, t-butyl hydroperoxide (TBHP), D(-) DIPT, Ti(O-i-Pr)4, I2, 1-heptyne, Pd(PPh3)4, CuI, and various reagents for specific reactions such as hydroborations and oxidative work-ups. The study concludes that the synthesized dimorphecolic acid from the rice plant exists as a mostly racemic mixture with the (S)-enantiomer being predominant, and the methods developed are applicable for synthesizing other HETEs, including 12(S)-HETE and 5(S)-HETE, with high optical purity and yield.
10.1021/ja4010267
The research involves several key chemicals that play crucial roles in the investigation of Z-selective ethenolysis and cross metathesis reactions. Methyl Oleate (6) is a standard substrate used to compare the ethenolysis reactivity and selectivity of metathesis catalysts. It is a fatty acid ester commonly used in olefin metathesis studies. 5-Decene (11) is an internal olefin used in cross metathesis reactions. The study investigates the reactivity of catalysts 3 and 5 with both cis- and trans-isomers of 5-decene. 8-Nonenyl Acetate (14) is another internal olefin substrate used in cross metathesis reactions. It is used in combination with 5-decene to study the formation of cross products.
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