The occurrence of the conifer, known as celery top pine Phyllocladus rhomboidalis, Rich.4) appears to be restricted to Tasmania. Distilled in July, the leaves, or, more correctly, the phyllocladia yielded 0,215 p.c. of volatile oil: d160,8892; «D - 12,3°; nD16o 1,4903; S.V. 1,5. It is difficultly soluble in diluted alcohol, but yields a clear solution with 1 vol. of absolute alcohol. The oil contains 1 p. c. of alcohols to which possibly the aromatic odor of the oil must be attributed. The lower boiling fractions of the oil contain 1-a-pinene (nitrosochloride, m. p. 108°; nitroso-pinene, m. p. 132°). In addition, the oil probably contains a sesquiterpene (d24o0,9209; aI)-h3,4°; nD23o1,5065), the chloro-formic solution of which is colored red by sulphuric acid. If bromine be added to the chloroformic solution of the sesquiterpene, a green color results, which darkens and finally changes to indigo blue. The distillation residue contains a colorless, crystalline substance of the following properties: m.p. 95°; [a]D +16,06°. Analysis revealed the formula C20H32, which was verified by a molecular weight determination. Its chloroformic solution is not colored by sulphuric acid.
1) Baker and Smith, A research on the pines of Australia. Sydney 1910, p. 397.
2) Report of Schimmel & Co. October 1910, 145. 3) Baker and Smith., loc. tit. 4) The same, loc. tit. p. 416.
Baker and Smith assume that the molecule has resulted from the unionof two molecules of pinene and regard it as a diterpene which they have named phyllocladene. It is scarcely attacked by potassium permanganate, but by chromic acid in acetic acid solution. With concentrated nitric acid it yields a nitro compound which melts indistinctly between 115 to 120°. It is soluble in concentrated sulphuric acid. With neutral permanganate solution it does not react. In glacial acetic acid solution it first adds bromine, but soon substitution takes place. Hence phyllo-cladene appears to be a saturated compound.