40707-88-8Relevant academic research and scientific papers
Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium
Amato, Maria E.,Ballistreri, Francesco P.,Pappalardo, Andrea,Tomaselli, Gaetano A.,Toscano, Rosa M.,Sfrazzetto, Giuseppe Trusso
, p. 13754 - 13763 (2014/01/06)
We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), a-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/ H2O2/pyridine. The reactions, performed in CH2Cl2/H2O at 25 °C, have shown good regioand stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), 1H-, 13C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.
Epoxidation of polyunsaturated fatty acid double bonds by dioxirane reagent: Regioselectivity and lipid supramolecular organization
Grabovskiy, Stanislav A.,Kabal'nova, Natalia N.,Chatgilialoglu, Chryssostomos,Ferreri, Carla
, p. 2243 - 2253 (2007/10/03)
The use of dimethyldioxirane (DMD) as the epoxidizing agent for polyunsaturated fatty acids was investigated. With fatty acid methyl esters, this is a convenient method for avoiding acidic conditions, using different solvents, and simplifying the isolation procedures, with less contamination due to by-products. The reagent was also tested with free fatty acids in water. In this case, the supramolecular organization of fatty acids influenced the reaction outcome, and the epoxidation showed interesting regioselective features. The C=C bonds closest to the aqueous-micelle interface is the most favored for the interaction with dimethyldioxirane. The preferential epoxidation of linoleic acid (=(9Z,12Z)-octadeca-9,12-dienoic acid) to the 9,10-monoepoxy derivative was achieved, with a high yield and 65% regioselectivity. In case of arachidonic acid (=(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid) micelles, the regioselective outcome with formation of the four possible monoepoxy isomers was studied under different conditions. It resulted to be a convenient synthesis of 'cis-5,6-epoxyeicosatrienoic acid' (=3-[(2Z,5Z,8Z)-tetradeca-2,5,8- trienyl]oxiran-2-butanoic acid), whereas in reverse micelles, epoxidation mostly gave 'cis-14,15-epoxyeicosatrienoic acid (= (5Z,8Z,11Z)-13-(3-pentyloxiran-2- yl)trideca-5,8,11-trienoic acid).
