Poy Nia TOY a a 
74 REPORT OF SCHIMMEL & Co. APRIL 1914. 
under the name of “Pagsainguin Oil”, and which was said to be the product of the 
resin of Canarium Cumingu, Engl. (N. O. Burseracece). It was pointed out afterwards — 
that the oil, as appeared from a paper by R. F. Bacon) was derived from another 
species of Canarium, to wit, C. villosum, F. Vill. Bacon found an oil of this kind to 
contain d-a-pinene, dipentene, and formic acid. We suspected at the time that the 
principal constituent of our sample, a pale-green oil (dis.0,8627; &p +-11° 3’; np0 1,47245; 
sol. in 3 vols. a.m. of 90 p.c. alcohol), was p-cymene. We are now able to report 
with regard to the chemical constitution of this oil that our surmise has been confirmed, 
but that for the rest we have found it to contain other hydrocarbons than those which 
had been found in it by Bacon. 
~The sample at our disposal amounted only to about 45 grams; it distilled over 
between 34 and 50° (4/5 mm.) and was split up in the following fractions: — 
34° (4 to 5 mm.); abt. 20 gr., camphoraceous odour. 
34 to 43° (4 to 5 mm.); abt. 5 gr., p.b. 167 to 171° (ordiipress): 
43 to 50° (4 to 5 mm.); abt. 15 gr.; odour of cymene. 
Residue: resinified oil. 
2 ACS Se 
The portions of the first fraction which distilled over between 161 and 164°, 
representing about 8 grams, were hydrated by the familiar method with glacial acetic 
and sulphuric acids; the ester-fraction (b. p. 65 to 80° at 5mm.) of the reaction-product 
being saponified with alcoholic potash. Although the saponified oil had a pronounced 
odour of isoborneol, we were unable to obtain from it any solid alcohol by cooling. 
Lack of material precluded us from definitely establishing the presence in the fraction 
of camphene. 
Portions of the 1St and 2"¢ fractions boiling between 164 and 169° (7 grams) were 
oxidised with an alkaline permanganate solution under ice-cooling, for the purpose of 
testing them for 6-pinene. The salt which crystallised out from the condensed oxidation- 
liquid in the form of the characteristic scales of sodium nopinate, afforded nopinic 
acid when acidulated, and after repeated recrystallisation this acid melted from benzene 
at 124 to 125°. The presence of $-pinene was thereby established. 
The characters of the 3'4 fraction were as follows: dis0 0,8620, «p + 8°26’. It gave 
no phellandrene-reaction. The bulk distilled over between 174,5 and 176°; in view of 
its unmistakable odour of p-cymene it was first of all oxidised with dilute perman- 
ganate solution, after which the unattacked oil, driven off with steam (which possessed 
almost the same properties as those of the original fraction), was further oxidised 
with strong permanganate solution at water-bath temperature. We only succeeded in 
obtaining minute quantities of p-hydroxyisopropylbenzoic acid, m. p. 155°, from which, 
by heating with hydrochloric acid, p-csopropenylbenzoic acid, m. p. 159 to 160°, was 
obtained, proof of the presence of p-cymene being thus afforded. It is certain, however, 
that the oxidised oil contained, in addition to a considerable proportion of p-cymene, 
another hydrocarbon of the terpene series. The portions of fraction 3 which boiled 
between 176 and 179° were tested for terpinene (nitrosite reaction) with a negative 
result. 
According to the investigation described above, pagsainguin oil therefore contains 
besides /-?-pinene, p-cymene, and probably also camphene. In any case, @-pinene forms 
the principal constituent. 
1) Philippine Journ. of Sc. 5 (1910), A, 257; Report April 1911, 60. . 
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