258 



BACON. 



resin in vacuo (4 to (J millimeters) giving a total of 390 grams of oil 

 (about 11 per cent). The latter had an odor like that obtained during 

 a similar distillation of Manila elemi (('. luzonicum A. Gray), and the 

 aqueous portion of the distillate contained a' considerable amount of 

 formic acid, although there were no visible evidences of decomposition 

 of the resin during the distillation in vacuo. The oil was then distilled 

 six times over sodium, using a column of glass beads in the neck of the 

 distilling flask, and gave the following fractions : 



Fraction No. 



Weight, 



Boiling 

 point. 



Retractive 



30 



index, N-g- 



Specific 



., 30 

 gravity, ^- 



Optical ro- 



30 



tation, A p. 



1 . ... . 



Grams. 

 102 

 19 

 45 

 40 

 47 

 10 



o 

 154-158 

 158-161 

 161-165 

 165-170 

 170-175 

 175-180 



1.4645 

 1.4660 

 1. 4690 

 1. 4730 

 1.4770 

 1. 4795 



852 

 851 

 850 

 849 

 849 



39.4 

 34.7 

 29.4 

 21.1 

 13.5 



2 



3 



4 ... 



5 . 



6. 









The residue was a thick, brown, viscous oil, which was attacked by 

 sodium when an attempt was made to distill it over that metal. 



Fraction No. 1 had a strong odor of pinene, and Nos. 1, 2, and 3 each 

 readily gave large yields of pinene hydrochloride, melting at 125°. 

 From the higher boiling fractions a very small quantity of dipentene 

 was obtained, the tetrabromicle melting at 124°. 



The principal constituent of the volatile oil of this sample of the 

 pagsainguin resin is therefore d-pinene. In a previous paper 3 I have 

 shown, from the examination of a very large number of specimens of 

 Manila elemi from individual trees, that the terpenes found in these 

 trees vary quite markedly from tree to tree, and that one tree usually 

 yields but a single terpene. The same would probably seem to hold 

 good for the pagsainguin resin, and it appears probable that these 

 Canarium trees manufacture a large series of terpenes and also the parent 

 substance of terpenes, p-eymol. The next step will be to study the resin 

 from one tree for a considerable length of time, to discover whether, 

 for example, an individual tree always gives a resin containing pinene, 

 or whether at one time it yields a product having pinene as .a constituent, 

 at another, a resin containing phellandrene, etc. This work will be 

 continued in this laboratory, as the resin should be of considerable value 

 in making clear the physiologic process of the plant in the formation of 

 resins. 



3 Loc. cit. 



