- 118 - 



The first and second fractions contained chiefly santene, the third 

 contained the bodies which we examined in special detail, and partly also 

 sesquiterpenes. The fifth and sixth fractions consisted almost entirely 

 of sesquiterpenes. 



isovaleric aldehyde. The first fraction possessed a particulary sharp 

 and acrid odour, which caused the presence of fatty aldehydes to be sus- 

 pected. We succeeded in isolating the latter by shaking with bisulphite 

 liquor. The product obtained by the decomposition of the bisulphite 

 compound (soluble in water), with soda, was however, not uniform but 

 boiled between 50 and 130°. One portion, b. p. 90 to 95°, consisted of 

 /sovaleraldehyde, of which the thiosemicarbazone, prepared in the familiar 

 manner, melted at 49 to 53 01 ). The fraction of which the b. p. lay bet- 

 ween 100 and 105° was particularly distinguished, by a sharp odour. No 

 n-valeric aldehyde, of which the b. p. is about 102°, could be detected. 



San ten e. The santene- fraction was purified by repeated crystalli- 

 sation over potash and sodium. The b. p. of the principal portion was 

 from 139 to 141°. The santene obtained by mixing the separate fractions, 

 possessed the following constants: b. p. 140 to 141° (770 mm.), di 5 o 0,869, 

 a D — 0°16', n D20O 1,46436. 



Santenone. The third principal fraction (d i5 o 0,9899; « D — 21°35') 

 consisted of a mixture of several compounds, from which we did not 

 succeed in separating single constituents by fractionation. In the course 

 of the examination of the first runnings of the sandalwood oil, F. Muller 2 ) 

 had isolated by means of semicarbazide from the portions boiling between 

 80 to 100° (15 mm.), a ketone CnH 16 0, called santalone, and identified 

 it from its semicarbazone and its oxime. Besides the santalone-semi- 

 carbazone, m. p. 175°, he obtained a still smaller quantity of a sparingly 

 soluble semicarbazone, melting at 224°. 



For the purpose of isolating the ketones, each separate portion of 

 the principal fraction (which was split up by careful distillation), was 

 treated with semicarbazide. From the fractions of which the b. p. lay 

 between 180 and 200°, (65 to 80° at 6,5 mm.), a considerable yield was 

 obtained of a semicarbazone which was sparingly soluble in alcohol. The 

 crude semicarbazone melted at 213 to 214°, and the purified product 

 obtained by repeated recrystallisation from alcohol, at 222 to 224°. 



0,1457 g subst.: 0,3270 C0 2 , 0,1171 g H 2 0. . 

 Found Calc. for Ci H 17 N 3 O 



C 61,21 °/o 61,52°/o 



H 8,93°/o 8,71 °/o 



*) Neuberg and Neimann (Berl. Berichte 35 [1902], 2052) give the m. p. of pure isovaler- 

 aldehyde thiosemicarbazone, as 52 to 53°. 



2 ) Arch, der Pharm. 238 (1900), 366; Report October 1900, 59. 



