— 124 



a mixture of mono- and di-acetate. The acid obtained by oxidation of 7 g. 

 of the enolic acetate with permanganate in acetone solution, when 

 recrystallised from alcohol, melted at 148 to 152°. 



0,1312 g. silver salt: 0,0518 g. Ag. 

 Found Calc. for Ci Hi 3 O 2 Ag 



Ag 39,49 °/o 39,54%. 



In order to establish the identity of the acid with teresantalic acid, 

 we isolated the latter from sandalwood oil by shaking with 3% caustic soda 

 liquor. The teresantalic acid obtained in this manner melted after repeated 

 recrystallisation from alcohol at 154 to 156°, and when it was mixed with 

 the acid prepared from the aldehyde the m. p. was not depressed. The 

 aldehyde which was isolated from the first runnings of sandalwood oil 

 is therefore identical with the nor-triq/cfoeksantalal which was obtained by 

 Semmler from eksantalal by the decomposition of santalol. 



Nor-triq/cfoeksantalal 



From E. I. sandalwood oil (Schimmel $ Co.) From santalol (Semmler) 



B. p 86 to 87° (6 mm.) 



d 20 o 0,9938 



« D — 38°48' 



Hd2oo 



Mol. refr 



Semicarbazone .... 

 Nor-tric*/cZoeksantalic acid 

 Teresantalic acid .... 



H 2 C 



m.p. 



H 



C 



1,48393 

 47,20 



223 to 224° 



91 to 93° 



148 to 152° 



.CH 3 



92 to 94° (11 mm.) 



0,9964 



— 30,8° 



1,48301 



47,00 



224° 



93° 



156° 



C — CH 2 — C 



t^ 



O 

 H 



I CH 2 I 

 HC C — CH 3 



v 



H 



Noreksantalal is the first aldehyde with 11 carbon atoms which has 

 so far been discovered in any essential oil. 



The body also occurs in the normal commercial sandalwood oil. 

 When treating 500 g. sandalwood oil with bisulphite we obtained from the 

 bisulphite compound (which dissolves in water) 0,82 g. aldehyde. The 

 semicarbazone melted at 221 to 223°; with noreksantalal semicarbazone 

 its melting-point was not depressed. 



Santalone. We tried, by careful fractionation, to isolate santalone 

 from the fractions which had been freed from nor-trict/cfoeksantalal, but 



