Commercial and scientific notes on essential oils. 41 



These statements seem to justify the conclusion that the alcoholic fractions of 

 the oil from West Australia contain a mixture of one or several sesquiterpene alcohols, 

 essentially not reacting with phthalic acid anhydride, and of santalol or of an alcohol 

 very similar to it. The result of the following oxidation tests would confirm the identity 

 of this alcohol with santalol. 



According to Semmler 1 ), santalal (wich is obtained from santalol by oxidation 

 with chromic acid anhydride in glacial acetic acid) of a boiling point of 152 to 155° 

 (10 mm.) yields a semicarbazone of a melting point of about 230°. In the repeated 

 preparation of santalal from santalol from East Indian oil we obtained on the con- 

 trary semicarbazone which melted between 215 and 219°; semicarbazones of the same 

 melting point were also obtained in repeated experiments with alcohols (from West 

 Australian oil) esterified with phthalic a6id anhydride by means of chromic acid and 

 glacial acetic acid. Depressions of the melting point amounting to more than 1° were 

 never observed in mixtures of the semicarbazones from santalol and the aldehyde 

 (from esterified alcohol of West Australian oil). 



Attempts to prove the presence of betulol by the preparation of tric^/cZobetulol 

 according to the method of Semmler 2 ) failed, both in the esterified and in the alcohol 

 preparations of West Australian oils of corresponding boiling point which did not react 

 with phthalic acid anhydride. 



From the fractions 1 and 2 we isolated by repeated fractionation a sesquiterpene 

 (65 g.) of b.p. 106 to 110° (3 to 4 mm.), d 15 o 0.9157; [«] D — 2°15'; n D20O 1.49968; this 

 fraction reacted only weakly with sodium on boiling. The solution in ether, saturated 

 with hydrogen chloride and strongly cooled, deposited after standing and evaporation 

 of the ether, scaly crystals which, recrystallised from methyl alcohol, melted between 

 79.5 and 80.5°. 



The analysis showed that these crystals represent a trihydrochloride, evidently 

 identical with that of bisabolene. 



0.1822 g. of the substance gave 0.2487 g. AgCl. 

 Chlorine found 33.76 per cent. Calculated as Ci 5 H 2 4(HCl) 3 33.97 per cent. 



Considering the small amount of this sesquiterpene-derivative its contents of this 

 oil can only amount to a few per cent. We, therefore, did not attempt in this 

 investigation to ascertain whether the oil really contains bisabolene as such, of a 

 sesquiterpene which passes into a derivative when treated with gaseous hydrochloric 

 acid. Since bisabolene is an aliphatic sesquiterpene of specific gravity 0.8759, we 

 should have to assume in our case that our sesquiterpene fraction was highly con- 

 taminated with some other sesquiterpene hydrocarbon of the same boiling point. 



We add here the results of tests of West Australian sandalwood oil conducted in 

 the Imperial Institute of London 3 ). The constants determined were:— di 5 o 0.958; 

 [«] D — 0°25'; n D 1.503; acid v. 2.9; ester v. 4.7; after acetylation 170.8; total alcohol 

 (Ci5H 24 0) 76.3 per cent; insoluble in alcohol of 70 percent. By oxidation with per- 

 manganate 8 per cent, of santalenic acid were obtained; an East Indian oil with 

 95 per cent, of santalol gave 24 per cent, of santalenic acid. These results likewise 

 indicate that small quantities of santalol were present in addition to other alcohols. 



In another journal 4 ) it is mentioned that sandalwood can be found in West Australia 

 on a area twice as large as Great Britain, and in small quantities also in Victoria, 

 New South Wales, and Queensland. It becomes more difficult, however, from year 



!) Berl. BeruMe 40 (1907), 1126. — 2 ) Ibidem 51 (1918), 420. — 3 ) Bull. Imp. Inst. 18 (1920), 162. 

 *) Chemist and Druggist 93 (1920), 1228. 



