RESULTS OF EXAMINATIONS. 29 



Table 6 shows that the specific gravity of the fractions gradually 

 decreases from the third to the ninth fraction. This may be due to 

 the presence of a small amount of limonene. However, on redis- 

 tillation, about 90 per cent of the fractions which first boiled between 

 162.4 and 194.9, boiled between 156 and 165, which showed that 

 they consist largely of pinene. The higher boiling point on the first 

 distillation may be explained by the retarding effect of the large 

 amount of high boiling sesquiterpene present. 



p-pinene. The portion which boiled between 160 and 170 on 

 redistillation, amounting to 12 per cent, was oxidized with K^Mn-jOg. 

 About 0.5 per cent of nopinic acid, the characteristic oxidation 

 product of /3-pinene, was recovered; it melted at 123. 



Cadinene. The residue boiling above 194.9 distilled between 

 118 and 145 at 20 mm. pressure. A fraction representing 50 per 

 cent of the total was collected between 135 and 140, the specific 

 gravity of which was 0.9173, the index of refraction 1.4925 and the 

 specific rotation [a] D = +15.41; the color was faint green. This 

 fraction, to which the characteristic odor of the original oil is due, 

 gave a dihydrochloride melting at 118. A 5.94 per cent solution of 

 the dihydrochloride in ether gave the optical rotation 00200= 1.89. 

 Cadinene is accordingly the sesquiterpene present. When five drops 

 of the cadinene fraction were dissolved in 2 c. c. of acetic anhydride 

 and a drop of concentrated sulphuric acid added a green color was 

 produced, which became blue, then purple, and finally red. When 

 glacial acetic acid 1 is used in place of acetic anhydride a red color is 

 produced almost immediately. This appears to be the first recorded 

 occurrence of cadinene in a turpentine oil. 



EXAMINATION OF THE ROSIN. 



A sample of WG rosin had the following properties: Specific 

 gravity, 1.060; acid number, 155.2; saponification number, 164.1; 

 ether number, 8.9. The rosin distilled between 240 to 255 at 10 

 mm. pressure. A few long prismatic crystals formed on the sides of 

 the receiver, but could not be isolated because of adherent oily prod- 

 ucts. The viscous distillate hardened to a faint yellow, amorphous 

 mass. All attempts to secure a crystalline body from either the 

 original rosin or the distilled rosin were unsuccessful. 



A portion of the white resin acids from the original oleoresin, 

 which had settled to the bottom of the container, was pressed in a 

 hand press until the greater portion of the intermingled liquid prod- 

 ucts had been removed. The white, waxy cake, after four crys- 

 tallizations from acetone, yielded crystals melting at 129 to 130. 

 When these were dissolved in hot absolute alcohol, and a few drops 



Compare Wallach, Annalen, p. 87, vol. 238, 1887. 



