M. Gargouri et Md. Legoy, CHEMOENZYMATIC PRODUCTION OF (-CORIOLIC ACID FROM TRILINOLEIN - COUPLED SYNTHESIS AND EXTRACTION()), Journal of the American Oil Chemists' Society, 74(6), 1997, pp. 641-645
Chemoenzymatic conversion of trilinolein to (+)-coriolic acid was inve
stigated in this work. Lipase-catalyzed hydrolysis of trilinolein and
lipoxygenation of liberated linoleic acid were coupled in a two-phase
medium that consisted of a pH 9 berate buffer and a water-immiscible o
rganic solvent (octane). High concentrations of trilinolein could be d
issolved in the organic phase (up to 340 mM). Linoleic acid, liberated
after hydrolysis, transferred to the aqueous phase and was enzymatica
lly converted to the preferred 13(S)-hydroperoxy-9Z,11E-octadecadienoi
c acid with soybean lipoxygenase-l. This product, which remained in th
e aqueous phase, could be recovered by centrifugation and then chemica
lly reduced to (+)-coriolic acid (purity >95%). Recovery of this compo
und by liquid-liquid extraction was easy. The structure of (+)-corioli
c acid has been confirmed by H-1 nuclear magnetic resonance spectrosco
py, mass spectrometry, and infrared spectroscopy. High yields were obt
ained with pure trilinolein or sunflower oil as initial substrates.