Estolides from fatty acids

Two of the three attractant pheromones identified to date are very close structurally to those used in primary metabolism. The biosynthesis of the estolide 5 probably starts from 3-hydroxybutyric acid (4), an intermediate in fatty acid biosynthesis (Fig. 4.3). Condensation of two units furnishes the pheromone 5. The formation of cupilure (3 Fig. 4.2) can be easily explained by two methylations from ubiquitous citric acid. Both compounds are unlike any known insect pheromones, whereas the third known attractant pheromone (ketone 1 Fig. 4.1), bears some resemblance to some insect pheromones. A proper comparison of the differences and similarities between insect and arachnid pheromones will require the identification of representative compounds from most of the families of both groups of organisms. 

D hydroxy esters or estolides by cleavage with fatty acids from high-oleic sun-... 

Fatty acids with polar substituents also retard the migration of triacylglycerols on TLC adsorbents, and those from seed oils that contain epoxy fatty acids can be separated into simpler species that contain from zero to three epoxide residue per mole. For example, silica gel layers and a solvent system of hexane-diethyl ether (3 1, v/v) were used to isolate such fractions from seed oils (Figure 9.1(B)) [192], Similar separations have been achieved with triacylglycerols that contain hydroxyl, estolide and other functional groups in the fatty acids. 

ESTOLIDES AND POLYCONDENSATION PRODUCTS FROM HYDROXY FATTY ACIDS... 

Cermak, S.C., Brandon, K.B., Isbell, T.A., 2006. Synthesis and physical properties of estolides from lesquerella and castor fatty acid esters. Ind. Crops Prod. 23, 54-64. 

Erhan, S.M., Kleiman, R., Isbell, T.A., 1993. Estolides from meadowfoam fatty acids and other monounsaturated fatty acids. J. Am. Oil Chem. Soc. 70, 461—465. 

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