— 126 — 



next Report, makes it probable that it represents teresantalol Ci Hi 6 O, 

 m. p. 113°, a body which has already been prepared by Semmler and 

 Bartelt 1 ) by reducing the ester of teresantalic acid with sodium and 

 alcohol. 



Santalene. The investigations of Guerbet 2 ), and more recently of 

 Semmler 8 ) have shown that the sesquiterpene of sandalwood oil may be 

 split up by fractionation into two hydrocarbons («- and /^-santalene), of 

 which the constants show marked divergencies. As the first runnings of 

 sandalwood oil consists to the extent of about 30% of sesquiterpene, we 

 took advantage of the occasion to prepare santalenes of the highest pos- 

 sible purity by careful fractionation. Without entering into details we 

 may state that the boiling point lay between 118 to 126° (7 mm.). As 

 the boiling point rose the density decreased and the rotation increased. 



Fraction 1: B. p. 118° (7 mm.); 252°(753 mm.); d 15o 0,9132; « D — 3°34'; 



n D15Q 1,49205; mol. refr. 64,87; 

 Fraction VI: B. p. 120° (7 mm.) . . . . ; d 20O 0,9058; « D — 11°10'; 



n D 2oo 1 ,49 062 ; mol. refr. 65,23; 

 Fraction IX: B.p. 121 to 122° (7 mm.); d 20 o0,8944; a D — 17°34'; 



n D20 ol,49110; mol. refr. 66,06; 

 Fraction XIII: B.p. 124° (7 mm.) . . . . ; d 20 o0,8939; « D — 23°40'; 



n D 2ool,49157; mol. refr. 66,17; 

 Fraction XVI: B. p. 125° (7 mm.) . . . . ; d 20 o0,8939; « D — 37° 40'; 



n D2 oo 1,49394; mol. refr. 66,43; 

 Last Fraction: B.p. 125 to 126° (7 mm.); d 20O 0,8940; a D — 41°3 f ; 



n D 2oo 1,49460; mol. refr. 66,53. 

 Comparison of the molecular refractions also demonstrated clearly 

 that the first fraction must contain a tricyclical, and the last bicyclical, 

 sesquiterpene. A similar favourable result of the fractionation is also 

 expressed in a comparison of the values of optical rotations. «-Santelene 

 had a rotation of « D — 3° 34'; /^-santalene of « D — 41° 3'. 



The fact, established by Semmler's experiments, that very close re- 

 lationship exists between the santalenes and the santalols (hydrocarbon 

 and alcohol), makes it probable that the rotation of pure ^-santalene is a 

 little lower than the value obtained by us. Perhaps «-santalene, like the 

 tricyclical «-santalol, may be faintly dextrorotatory. This is very clearly 

 shown by comparing the constants of the santalenes with the values re- 

 cently observed by us for «- and /?-santalol (purified by means of the acid 

 phthalic esters). We have also added to our table the constants of san- 

 talene observed by Guerbet and by Semmler, thus showing still more 

 clearly the success of the improved separation. 



*) Berl. Berichte 40 (1907), 3101 ; Report October 1907, 88. 



2 ) Compt. rend. 130 (1900), 417; Journ. de Pharm. et Chim. VI. 9 (1900), 224; Report 

 April 1900, 42. 



3 ) Berl. Berichte 40 (1907), 3321 ; Report October 1907, 85. 



