NEW PHILIPPINE ESSENTIAL OILS. 



343 



The neutral portion, weighing 9.3 grams, -was distilled at 16 millineters 

 pressure. The following fractions were obtained: 



Fraction. ^^^^^ Weighu I 



TTT 



'C. Grams. 



80to90 ■ 3.8 



90to98 2.0 



98 to 110 1.5 



UOtolSS 1.0 



[ 



Residue 



1.0 



Fractions I and II were united and treated with phthalic anhydride in 

 benzene, but no primary alcohols were obtained. The odor of the oil was very 

 suggestive of linalool. Oxidation with chromic acid mixture gave citral, which 

 was identified by its B-naphthocinchoninic acid compound melting at from 196° 

 to 197°. 



Fraction lU appeared to consist of a mixture of the second and fourth frac- 

 tions. 



30° 

 Fraction IV, weight about 1.0 gram, had a specific gravity, — ^, of about 



on° 

 1.09. and the refractive index, '—-, 1.5130. Its odor somewhat resembled that 



D 



of methyl eugenol. Therefore it was oxidized with potassium permanganate 



in the cold, and about 0.15 gram of veratric acid, melting point 179° to 180°, 



was obtained. 



No phenolic substances were identified with certainty. After passing carbon 

 dioxide into the alkaline solution and extracting with ether, 5.5 grams of oil 

 were obtained. An attempt was made to distil this portion at 13 millimeters 

 pressure, but only a few drops distiUed below 200°. This distillate had a 

 strong odor closely resembling that of thymol. Although it behaved toward 

 alkalies as a phenol it gave no color with ferric chloride, resembling thymol 

 in this respect. It did not crystallize, probably owing to the presence of other 

 substances. 



The residue in the distilling flask appeared to have polymerized to a resin. 



After the neutral and phenolic stibstanees had been removed, the solution was 

 acidified with sulphuric acid and extracted with ether. After evaporation of 

 the ether the acids were neutralized with soda and a dilute solution of calcium 

 acetate was added. This removed most of the chlorophyll and a small amount 

 of one of the higher fatty acids." The methylethyl acetic acid in the filtrate 

 was precipitated as the silver salt, weight 1.2 grams. 1.2000 gram of substance 

 gave 0.624 gram Ag. 



Calcalaied for CsHjO^Ag. 

 per cent. 



A2= 51.4 



Found, 

 per cent. 



52.0 



"The substances other than methjlethyl acetic acid in the acid fraction 

 weighed about 0.5 gram. These appeared to c-onsist of chlorophyll and a very 

 small amount of a liquid, odorless, fatty acid. 

 104660 5 



