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Hexadecanol, together with the less amount of tetradecanol, was found to occupy the greater part of fatty alcohols in pollack viscera oil. Two monoethenoid alcohols were isolated as minor components, and identified as Δ10-eicosenol and Δ11-docosenol, respectively. This may be the first finding of the occurrence of Δ10-eicosenol in marine animal oils. Unsaponifiable matters (364g) obtained from commercial pollack viscera oil (29.7kg) were dissolved in about one litre of acetone and left stand overnight to remove the most part of sterols. The remaining liquid unsaponifiables (198g) were acetylated, and divided into five fractions by distillation under the reduced pressure, as shown in Table 1. Alcohols in each fraction were purified by alumina column chromatography and fractional crystallization from acetone at low temperature. From the fractions I and II, tetradecanol (m.p. and mixed m.p. 37.8°C) and hexadecanol (m.p. and mixed m.p. 49.5°C) were obtained. They were also derived to phenylurethane or α-naphthylurethane for identification. Colorless plates (m.p. 24.5-25.0°C) from the fraction III, were identified as Δ10-eisocenol, by obtaining eicosanol (m.p. 65-66°C) on the hydrogenation in the presence of palladium black and two decomposition products, capric and sebacic acids, on the oxidation with potassium permanganate and chromic acid. By the similar method, the monoethenoid alcohol from the fraction IV, was identified as Δ11-docosenol (m.p. 31.5°C), which gave docosanol (m.p. 70-70.5°C) on hydrogenation and both undecanoic and undecadioic acids on oxidation. From the fractions III, IV and V, the considerable amounts of cholesterol and cholesta-3, 5-diene, a pyrolysis product of cholesteryl acetate, were isolated.
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