The leaves of Litsea odorifera, Valeton, one of the Lauraceae of Java, are known there as trawas leaves and are sold as a popular remedy. According to van Romburgh1) they yield a volatile oil of the following properties: d15o0,836 to 0,846; aD - 0°10' to - 7° (in a 200 mm. tube). The bulk of the oil distils at 233° (120 to 125° under 10 mm. pressure). With semicarbazide it forms a semicarbazone melting at 116°, from which a ketone was regenerated. This ketone van Romburgh treated with potassium permanganate and thus obtained another ketone (m.p. 12°; b.p. 234°; d17o0,829; m.p. of semicarbazone 124°) which proved to be methyl nonylketone. From the oxidation liquid, an acid C10H18O3, m.p. 49°, viz., 2-ketodecylic acid, was isolated. Upon oxidation with chromic acid and sulphuric acid, it yielded suberic acid, whereas upon oxidation with sodium hypobromite it yielded azelaic acid and carbon tetrabromide. Hence the unsaturated ketone contained in the oil must be nonylene-1 -methyl ketone. Inasmuch as the semicarbazone mixture obtained from the original oil could not be resolved into its components by recrystallization, the regenerated ketone mixture was brominated with a methyl alcoholic solution of bromine. When thus treated it was almost exclusively the unsaturated ketone which reacted. After the saturated ketone had passed over, the dibromide distilled at 204° (15 mm.). From this the bromine was removed by means of zinc dust and alcohol, whereby a ketone with the following properties resulted: m.p. - 7°; b.p. 235°; d11,5o0,848; mol. refr. 52,47; computed for C10H20O/7 52,51.
In like manner the alcohols of the trawas oil were separated. They proved to be \-methyI-n-nonylcarbinol (aD - 5° 40') and undecene-1-ol-10 (b. p. 233°; d10o0,835). The methylnonyl-carbinol was characterized by oxidation to methyl-n-nonylketone. The undecenol yielded, upon oxidation with chromic acid and sulphuric acid, a ketone the semicarbazone of which melted at 113°. Upon oxidation with potassium permanganate it yielded 2-ketodecylic acid.
1) Koninkl. Akad. Wetensch. Amsterdam, Meeting of Oct. 28, 1911, p. 325; Report of Schimmel & Co. April 1912, 121. Four oils labeled as Trawas olie1), when examined in the laboratory of Schimmel & Co., revealed the following properties: d16o0,9084 to 0,9222; aD - 18°7' to - 20°54'; nD20o1,46377 to 1,46506; soluble in 1 vol. or more of 80 p.c. alcohol, the diluted solution showing faint opalescence. One of the principal constituents is cineol2), the presence of which could be recognized by its odor. In other respects the odor reminded one of that of cardamoms.