ARS | Publication request: Synthesis and Characterization of Some Oxygenated Fatty Compounds

Submitted to: Meeting Abstract
Publication Type: Abstract
Publication Acceptance Date: August 15, 2002
Publication Date: August 20, 2002
Citation: KNOTHE, G.H., KENAR, J.A. SYNTHESIS AND CHARACTERIZATION OF SOME OXYGENATED FATTY COMPOUNDS. World Conference and Exhibition on Oilseed and Edible, Industrial and Specialty Oils. Istanbul, Turkey. 2002. ABSTRACT. p. 14.

Technical Abstract: Oxygenated fatty acids occur naturally in numerous fats and oils. Some notable examples are castor oil containing significant amounts of ricinoleic acid (a hydroxy acid), lesquerella oil containing lesquerolic and auricolic acids (both hydroxy acids), and vernonia oil containing vernolic acid (an epoxy acid). The oxygenated functionalities impart other properties and potential uses to these materials, so that derivatizations of common vegetable oils such as soybean oil or their components to give similar materials are of significant interest. Several pathways exist for achieving this. These pathways include microbial conversions and chemical syntheses. Chemical syntheses can mimic naturally-occurring compounds or those obtained by microbial conversions as well as offer routes to yet unknown moieties. Direct oxidation of monounsaturated fatty compounds with SeO2 / tert.-butylhydroperoxide yields materials with allylic hydroxy groups (enols and diastereomeric 2-ene-1,4-diols) and with SeO2 / H2O2 vicinal hydroxy groups (1,2-diols) are obtained via isolable heterocyclic selenite intermediates. Diketones (1,2-diones) were synthesized by direct oxidation of monounsaturated fatty esters with KMnO4. Chain extension of terminal olefinic fatty esters with nitrile oxides affords 2-isoxazoline heterocycles which in turn can be converted into beta-hydroxy ketones by reductive hydrogenolysis-hydrolysis using Raney nickel. The products were systematically characterized by methods such as gas chromatography - mass spectrometry and 1H and 13C nuclear magnetic resonance spectroscopy. "Migration" of the functionalities along the fatty acid chain causes often systematic effects in the spectra of the products.