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A selective acylation protocol using cerium chloride (CeCl3) as catalyst was applied to functionalize silybinin (1), a natural antioxidant flavonolignan from milk thistle fruit, in order to increase its solubility in lipophilic media while retaining its strong antioxidant activity. The selective esterification of 1 at the position 3-OH with a palmitate acyl chain leading to the formation of the 3-O-palmitoyl-silybin (2) was confirmed by both mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses. The antioxidant activity of 1 was at least retained and even increased with the CUPRAC assay designed to estimate the antioxidant activity of both hydrophilic and lipophilic compounds. Finally, the 3-O-palmitoylation of 1, resulting in the formation of 2, also increased its anti-lipoperoxidant activity (i.e., inhibition of conjugated diene production) in two different lipophilic media (bulk oil and o/w emulsion) subjected to accelerated storage test.

Adsorptive desulfurization was studied using straight-run gas oil (SRGO) with various sulfur contents (390 and 60 ppm S). Immobilization of electron-poor molecules (π-acceptors) on macroporous resins was achieved in three steps starting from commercially available poly(styrene-co-divinylbenzene) beads. Influence of the temperature on adsorption was studied, and the process was examined on the basis of breakthrough curves. The regeneration of the support was studied using fixed-bed technology and was efficiently performed with toluene as the solvent. The extracted compounds were easily recovered after evaporation of the toluene and the affinity of the resins toward alkyldibenzothiophenes was confirmed by GC-FPD analysis. On the basis of these preliminary experimental results, a new concept is proposed for ultradeep desulfurization of SRGO. [ABSTRACT FROM AUTHOR]