- 56 - 



removal of the linalool, or addition of waste products which originate 

 from the manufacture of linalool from linaloe oil, exert a rather large 

 influence on the rotation of the oil, which not infrequently changes 

 into dextrorotation, whilst the other properties are but slightly altered. 

 But the saponification number which in normal oil lies between i and 25, 

 generally increases then up to 30- — 45, and thus also becomes a betrayer 

 of the adulteration. In such case fractional distillation in vacuo will 

 readily show that the oil is poor in linalool, and therefore adulterated. 



On the other hand, dextrorotation can also be often observed in 

 linaloe oil, if the individual fractions collected during the distillation 

 are not mixed equally. Fractional distillation will here also give the 

 required information, at any rate 1-linalool can always be isolated from 

 such an oil. 



For this reason the observation made in our laboratory is all the 

 more interesting, that dextrorotatory linaloe oil of otherwise good quality 

 also exists. 



The oil examined had the following constants: d 15 o 0,8793; 

 a D -\-7°5 l 'i ac id number 1,02; ester number 3,88; soluble in 1,7 

 and more vol. 70 per cent, alcohol. 



This oil differs from the above-described abnormal oil by its low 

 ester number, and the further examination showed that the oil was 

 quite normal. On fractional distillation a fraction boiling between 94 

 and 98 (13 mm.) was obtained, which represented about 65°/ of the 

 oil, and which was identified on further examination as d- linalool: 

 d 15 o 0,8701; «d -|- ii° 15'; n D20° 1,46209. The phenyl urethane 1 ). 

 produced from it melted at 65 ; oxidation with chromic acid mixture 

 yielded citral. 



Unfortunately we have been unable to ascertain anything more 

 definite about the origin of the oil, and we must therefore content 

 ourselves with mentioning the observation made by us. 



Matico Oil. Some time ago Fromm and van Emster 2 ) reported 

 on the composition of matico oil. The authors isolated from the 

 heavy portions of an oil distilled by us, as principal constituent, an 

 unsaturated phenol ether "matico ether", to which they ascribed the 

 formula of a methylbutenyl-dimethoxy-methylenedioxybenzene. On 

 oxidation matico ether yielded an aldehyde and also an acid; with 

 regard to the relative situation of the substitutes in the benzene- 

 nucleus nothing was stated. Thorns 3 ) took up the examination of 



*) The linalylphenyl urethane, in 10 per cent, alcoholic solution, showed a rotation 

 of -\- i° 6'. As a trial showed that the phenyl urethanes rotate in the same way 

 as the corresponding linalools, this also proves that we had here to deal with 

 d - linalool. 



2 ) Berl. Berichte 35 (1902), 4347, — Report April 1903, 51. 



3 ) Arch, der Pharm. 242 (1904), 328. 



