GC/EI-MS Determination of the Diastereomer Distribution of Phytanic Acid in Food Samples
Phytanic acid (3,7,11,15-tetramethylhexadecanoic acid) is a branched-chain fatty acid, produced by bacteria by means of oxidation and biohydrogenation of the chlorophyll side chain phytol (3,7R,11R,15-tetramethylhexadec-2-en-1-ol). The later reaction generates to a new stereogenic center on C-3 which can be both 3R- or 3S-configured. Thus, two diastereomers (3S,7R,11R,15- and 3R,7R,11R,15-phytanic acid) are naturally produced. In this study we examined the diastereomer composition of phytanic acid in terrestrial and marine food samples. Phytanic acid was transferred into its methyl ester which was analyzed by GC/MS in the selected ion monitoring mode. The first eluted diastereomer in the samples was tentatively identified as 3S,7R,11R,15-phytanic acid. The marine samples were clearly dominated by 3S,7R,11R,15-phytanic acid whose abundance was higher in marine mammals than in fish. Milk from one organic cow collected over a period of 30 days showed lower proportions of 3S,7R,11R,15-phytanic acid than milk from one cow raised with conventional feed. The difference between organic and conventional dairy products (cheese and butter) was not as pronounced as in milk. Milk samples from other mammals (goat, sheep, mare, camel, moose, and human) also showed an excess of 3S,7R,11R,15-phytanic acid except for camel and moose milk.
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