Labeling Fatty Acids by Exposure to Tritium Gas. III. Methyl Stearolate and Methyl Linolenate

Journal Article · Sun Jul 01 04:00:00 EDT 1962 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo01054a511· OSTI ID:4675778

Dutton, H. J.; Jones, E. P.; Davison, V. L.; Nystrom, R. F.

The 12,13- and 9,10-double bonds of methyl linoleate were found to add tritium in a ratio of 1.4 to 1, respectively. The acetylenic fatty acid ester, methyl stearolate, on exposure to tritium and on subsequent analysis was shown to yield cis- and trans-9,10-tritiooctadecenoate as the major radiochemical product and to give minor amounts of radioactive methyl stearate (saturation) and stearolate (substitution). Radioactivity observed in the C/sub 9/ dibasic and C/ sub 9/ monobasic acids resulted from substitutlon by tritium for the carbon- bonded hydrogen at carbon atoms other than numbers 9 and 10. Radioactivity in the C/sub 9/ mono- and dibasic acids corresponded to the 3 to 4% tritiated methyl stearolate isolated by liquid-liquid chromatography and gas-liquid chromatography before oxidation; radioactive stearic acid corresponded to the 9% tritiated stearic acid similarly isolated by chromatography of the uncleaved fatty acid esters. The octadecatrienoate ester, methyl linolenate, on tritium exposure and oxidative cleavage yielded some radioactive mono- and dibasic acids. Unexpectedly, a comparatively iarge amount of activity (20.3%) was associated with the linolenate peak, indicative of considerable reactlon by substitution. (TCO)

• Research Organization: Northern Regional Research Lab., Peoria; and Univ. of Illinois, Urbana
• Sponsoring Organization: USDOE
• NSA Number: NSA-17-025297
• OSTI ID: 4675778
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 7 Vol. 27; ISSN 0022-3263
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

BINDING ENERGY
CARBON
CHEMISTRY
CHROMATOGRAPHY
ESTERS
HYDROGEN
LABELLED COMPOUNDS
LINOLEIC ACID
LIQUIDS
METHYL RADICALS
ORGANIC ACIDS
OXIDATION
TRITIUM