— 72 — 



to consist in great part of the alcohol terpinenol, which also occurs 

 in oils of cardamom and majoran. The sample of juniper oil which 

 was used by us for the purposes of investigation had the following 

 constants, viz., d^o 0,8740, «d — 7 20', sap. no. 7,2. In order to 

 recover the oxygenated portions of the oil, which are more readily 

 soluble in dilute alcohol than are the hydrocarbons, the sample was 

 extracted repeatedly with 70 per cent, alcohol, and the body which 

 was found in the alcoholic extract recovered after the solvent had 

 been distilled off. It appeared in the form of an oil possessing a 

 pleasant odour of juniper berries, and was found to possess the foll- 

 owing constants: d^o 0,9300, «d — 3°44- / , sap. no. 21,8, sap. no. after 

 acetylation 136, corresponding to 41,65 per cent, alcohol C 10 H 18 O. 

 The alcohol -content, determined by Boulez' method 1 ), was 56,2 °/ 

 C 10 H 18 O. When the oil was fractionated (8 mm.) 7o°/ passed over 

 between 86 and 110 , while 3O°/ distilled between no and 155 . 

 From the principal part a portion was separated by repeated frac-' 

 tionation. This was found to consist in the main of terpinenol -4, 

 and possessed the following constants: b. p. 93 to 95 (8 mm.) 215 

 to 220 (750 mm.); di 5 o 0,9400; «d -j- I3°6 r . Oxidation of this 

 fraction with diluted permanganate of potassium, under cooling, gave 

 a glycerin, 1, 2, 4 - trihydroxy terpane, m. p. 114 to 11 6°, which had 

 already been obtained by Wallach 2 ) from terpinenol-4. 



Analysis: 0,1350 g material: 0,3150 g C0 2 , 0,1256 g H 2 0: 

 found : calculated for C 10 H 20 3 : 



C 63,64 63,83 o/ 



H 10,34 10,63% 



When this glycerin was boiled with dilute sulphuric acid there 

 was formed, in addition to cymene, carvenone, which was identified 

 from its semicarbazone, m. p. 202 . When further oxidised with per- 

 manganate, the glycerine also yielded a, a'-dihydroxy-a, a'-methyl iso- 

 propyl - adipic acid, m. p. 205 . Inactive acid was probably mixed 

 with this body, because when it was boiled with hydrochloric acid the 

 result was not the dilactone of the active acid, melting at 63 to 64 , 

 but the dilactone with m. p. 73 to 74 , which, according to Wallach, 

 is a derivative of i-a, a'-dihydroxy-a, a'-methyl w^-propyladipic acid. 

 Part of the principal fraction was warmed up with twice its quantity of 

 1 00 °/ formic acid, when water was given off, and hydrocarbons pro- 

 duced, which partly distilled at 180 . When the hydrocarbons were 

 oxidised with diluted solution of permanganate the resultant products 

 were the erythritol, m. p. 237 to 23 8°, characteristic of 7-terpenene 

 and i-a, a'-dihydroxy-a, a'-methyl /^-propyladipic acid, m. p. 188 , 



1 ) Comp. Report April 1907, 120. 



2 ) Liebig's Annalen 362 (1908), 278; Report November 1908, 179- 



