Isolation and preliminary characterization of 1-O-Octadec-cis-11-enyl glycerol from Paramecium phospholipids

1-O-Octadec-$\text{cis}$-11-enyl glycerol, paramecyl alcohol, was isolated from $\text{Paramecium}\text{tetraurelia}$ and $\text{P.}\text{caudatum}$ phospholipids. This isomer of 1-O-octadec-9-enyl glycerol, selachyl alcohol, had not been previously reported as a component of naturally-occurring phospholipids. The preliminary characterization of the structure of this compound was determined by 1) gas chromatography of the parent compound as well as the products following hydrogenation, ozonolysis and oxidation, 2) mass spectrometry of the parent compound and an oxidation product, 3) infrared spectroscopy, and 4) proton magnetic resonance.