Confirmation by gas chromatography/mass spectrometry of two unusual trans-3-monoethylenic fatty acids from the Nova Scotian seaweeds Palmaria palmata and Chondrus crispus.
The structures of two unusual fatty acids, the known trans-3-hexadecenoic acid and a novel trans-3-tetradecenoic acid, both isolated from the Nova Scotian seaweeds Palmaria palmata and Chondrus crispus, were positively identified. After the extraction of the total fatty acids by saponification, followed by methylation, the monoenoic trans fractions were isolated by thin-layer chromatography on silica gel impregnated with silver nitrate. The monoenoic trans fractions were derivatized with 2-amino-2-methyl-propanol prior to analysis by gas chromatography/mass spectrometry. The mass spectra showed prominent [M + 1]+ ions but lacked the 12 amu interval useful for identifying the double bond position. Hence, alternative diagnostic peaks were used to confirm the position of the double bond in these two fatty acids. As the trans-3-hexadecenoic acid is found in the photosynthetic tissue of all plants, it may also be present in ruminant fats and, presumably, in human adipose tissue.
Lamberto
M
M
Canadian Institute of Fisheries Technology, Technical University of Nova Scotia, Halifax, Canada.
Ackman
R G
RG
D002021:Buffers; D002855:Chromatography, Thin Layer; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry* / Q000302:isolation & purification; D008401:Gas Chromatography-Mass Spectrometry; D013058:Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D009674:Nova Scotia; D010169:Palmitic Acids / Q000737:chemistry* / Q000302:isolation & purification; D011412:Propanolamines; D012624:Seaweed / Q000737:chemistry*
C089481:3-tetradecenoic acid; D002021:Buffers; D005229:Fatty Acids, Monounsaturated; D010169:Palmitic Acids; D011412:Propanolamines; C070982:delta(3)-hexadecenoic acid; C006551:2-amino-2-methyl-1-propanol