Origin and Production3)4)5). The oil distilled, with a yield of about 0,45 p.c, from the fresh leaves and twigs of the kobuschi tree, Magnolia Kobus, DC. (family Magnoliaceae), which occurs in the interior of japan, is light yellow in color and possesses the following properties: d15o0,9432 to 0,9642; aD - 1°6'to- 1°32'; A.V. 0,7 to 1,5; E.V. 4,3 to 8,87; soluble in 1,2 to 10 vol. of 80 p.c. alcohol, the strongly diluted solution of which reveals opalescence; soluble in 0,5 to 1 vol. of 90 p.c. alcohol to a clear solution.
1) Apotheker Ztg. 19 (1904), 46.
-') Midland Drugg. and pharm. Review 45 (1911), 486.
3) Report of Schimmel & Co. October Ims, 78.
4) E. Charabot and G. Laloue, Compt. rend. 146 (1908), 183; Bull. Soc. chim. IV. 3 (1908), 381.
5) Report of Schimmel & Co. April 1908, 61.
Composition. The oil, which boils between 190 and 230 , contains cineol*) (resorcinol derivative), about 15 p.c. citrai1)'1)2) and 16 p.c. anethol2) (m.p. of anisic acid 184°; m.p. of anethol dibromide 66 to 67°). Probably methylchavicol is also present. Whereas the corresponding fraction could not be made to congeal at first, it solidified readily after boiling for two hours with strong alkali (re-arrangement to anethol)3). However, safrol, the presence of which was at first suspected1), is not a constituent of the oil.
An oil distilled in the province Shizuoka from very young twigs and examined by Y. Asahina and H. Nakamura4) differs in part from the oils described above. It was light yellow and possessed a citral-like odor: d15o 0,982; aD + 6°8'; A. V. 4,3; S.V. 19,1; E.V. after acetylation 56,48; soluble in 1,4 volume of 85 p. c. alcohol, the addition of more alcohol producing opalescence. Of its constituents the following were identified: citral (6 to 7 p.c; m.p. of B-citryl-B-naphthocinchoninic acid 197 to 200°), eugenol (m.p. of benzoyl derivative 69°), cineol (m.p. of cineol-iodol 112 to 113°, m.p. of cineolic acid 195°), and methyl-chavicol as principal constituent. Upon oxidation with potassium permanganate it yielded homoanisic acid (m.p. 84 to 85°) and anisic acid (m.p. 184°). Possibly the oil also contains pinene, for fraction 150 to 160° yielded traces of a nitrosochloride which, however, could not be characterized because of the small amount. Of acids the presence of caprinic acid (silver salt 38,52 p.c. Ag) and oleic acid (silver salt 27,54 p.c. Ag) were ascertained. It is noteworthy that the oil examined by Asahina and Nakamura contained no anethol but eugenol which was wanting in the oils previously examined.