Microbial oxidation of oleic acid

ABSTRACT

Resting cells of Saccharomyces cerevisiae converted oleic acid [I] into 10-hydroxyoctadecanoic acid [II] in 45% yield. Nocardia aurantia [ATCC 12674], Nocardia sp. [NRRL 5646] and Mycobacterium fortuitum [UI 53378] have also converted oleic acid into 10-oxo-octadecanoic acid [III] in 65%, 55% and 80% yield, respectively. N. aurantia resting cells transformed III into the corresponding methyl ester [IV] in 37% yield. Structures of all metabolities were suggested by PMR and 13C- NMR, IR and mass spectrometry. The chemical Bayer-Villiger oxidation technique with 10-oxo-octadecanoic acid, followed by mass spectral analysis of neutral extracts, has been used to confirm the position of the oxo-functional group in the structures of keto-fatty acid. The PMR analysis of diastereometric S[+].O-acetylm and elate esters of hydroxystearate proved to be efficient in ascertaining stereochemical purities of hydroxy fatty acids