206978-14-5Relevant articles and documents
Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract
Siskos, Elias P.,Mazomenos, Basilis E.,Konstantopoulou, Maria A.
, p. 5577 - 5581 (2008)
Three active components were identified by bioassay-guided fractionation of bitter orange (Citrus aurantium L.) fruit peel petroleum ether extract. Silica gel fractionation of the extract yielded a fraction that inflicted up to 96% mortality to adults of the olive fruit fly Bactrocera oleae (Gmelin) three days post-treatment. Subsequent HPLC purification of the active fraction resulted in the isolation of three components, eluted in fractions F222, F 224, and F226, that induced adult mortality. Considering the data obtained from UV, FTIR, MS, and 1H NMR spectra, they were identified as 7-methoxy-8-(3′-methyl-2′-butenyl)-2H-1-benzopyran-2- one (osthol), 4-methoxy-7H-furo[3,2-g]benzopyran-7-one (bergapten), and 4-((E)-3′-methyl-5′-(3″,3″-dimethyloxiran-2″-yl) pent-2′-enyloxy)-7H-furo[3,2-g][1]benzopyran-7-one (6′,7′- epoxybergamottin). Our results are in concordance with those reported in the literature and were further verified by direct comparison to authentic components. 6′,7′-Epoxybergamottin was toxic when tested individually, while bergapten and osthol were found to act synergistically to 6′,7′-epoxybergamottin.
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.
SYNTHESIS OF SPIRO ORTHO ESTERS, SPIRO ORTHO CARBONATES, AND INTERMEDIATES
-
Page 29-30, (2008/06/13)
Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synt
