[Uropygial gland fat of the fulmar].

Isolation of nonacosan-10-ol: The extract, after being digested with methanol and concentrated into a small volume, was chromatographed over silica gel with hexane to isolate a crystalline substance. The crystalline substance was recrystallized from hexane: mp 83 -84 ° , [a]D ± 0 ° , C29H60O (M® ion m/e 424; found: C 81.84%, H 14.30%; calc.: C 81,99%, H 14.24%). Acetylation of nonacosan-10-ol: The alcohol (50 mg) was acetylated by treating with acetic anhydride (0.3 ml) in pyridine (1 ml) at room temperature overnight. After addition of water (10 ml), the reaction mixture was extracted with ether (15 ml) to obtain an acetylated product as an oily substance: VmSt 1736, 1465, 1380, 1240 and 1034 cm 1 . Oxidation of nonacosan-lO-ol into nonacosan-l 0-one: Nonacosan-10-ol (35 mg) dissolved in glacial acetic acid (10 ml) was stirred with sodium dichromate (10 mg) at 80° for 10 min. The reaction mixture, after being diluted with water (20 ml), was extracted with petroleum ether (15 ml) 3 times. The petroleum solution was washed with a 5%-aqueous solution of sodium carbonate, dried over sodium sulfate and petroleum ether distilled out to obtain a crystalline substance: mp. 6 9 7 0 ° , vL«Nujol1710, 1465 and 1380 cm"1. Isolation of cuparene: The oily substance separated by the above elution chromatography of the extract was successively subjected to preparative gas-chromatography. An oily substance was thus isolated in a pure state with respect to gas chromatography (PEG 6000 and DEGS) and thin-layer chromatography (silica gel and hexane): C15H22 m/e 41 (31%), 55 (15%), 91 (23%), (10%), 187 (3%) and 202 (M®, 17%).