| Abstract: | Twelve male weanling rats were divided equally into 3 groups and placed on fat-free diets. The diets of groups 1 and 2 were supplemented with 0.54% of racemic methyl cis-9,10-methylene octadecanoate (CMO) and racemic methyl trans-9,10-methylene octadecanoate (TMO), respectively. Group 3 served as a control. Gas liquid chromatographic analysis of the adipose tissue as methyl esters indicated that, at the level fed, cyclopropane fatty acids do not affect normal fatty acid metabolism as do the cyclopropene fatty acids. Gas liquid chromatography (GLC) analyses of groups 1 and 2 revealed the presence of a different unidentified fatty acid for each of the acids fed in addition to the CMO and TMO acids themselves. Each of the unidentified acids and the CMO and TMO acids were isolated and purified by preparative GLC. The absolute identity of the CMO and TMO acids fed and isolated from body fat was established by IR, NMR, and mass spectra. The biodegradation products of the CMO and TMO esters were shown to be cis- and trans-3,4-methylene dodecanoic acid, respectively. Unequivocal proof of structure was established through synthesis followed by comparison of IR, NMR, and mass spectra, melting points, GLC retention times, and elemental analyses with those obtained for the degradation products. ... |
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