PHILIPPINE TERPENES AND ESSENTIAL OILS, IV. 263 



while warm, but when cooled, solidified to a crystalline mass, like rose oil. In 

 1894 - the same firm speak of a ehampaca oil of a reddish-yellow color, with an odor 

 reminding one somewhat of cassia flowers, which also separated considerable 

 quantities of crystals. In 1897 8 this firm obtained a ehampaca oil originating 

 ih Manila, of specific gravity of 0.938, optical rotation. — 58°. 2 and ester number 

 77.3. They also state that the oil had -a slight resemblance in odor to that of 

 ylang-ylang and, like the latter, contained benzoic acid. In 1907 10 the same 

 firm report the following substances as occurring in ehampaca oil : Linalool, about 

 00 per cent; small amounts of geraniol and of eugenol methyl ether; and in the 

 lower boiling portions, the methyl ester of methyl ethyl acetic acid. 



In so far as Manila oils are concerned, I consider that these reports 

 do not represent an oil from the yellow ehampaca flower, as so far as I am 

 ahle to learn there never has been a time in Manila when as much as 1,000 

 kilos of flowers were available at any one time. 



1 have worked only with the oil from the yellow ehampaca, and have 

 not made any studies on the one from the white flowers. It is probable 

 that these reported oils represent distillations of ehampaca mixed with 

 other flowers. In the Manila oil of 1897 these other flowers were prob- 

 ably ylang-ylang, because of the odor and physical properties of the 

 oil and of the presence of benzoic acid, which I do not find in my eham- 

 paca oils. 



Several synthetic oils have been announced, the only one of which I 

 have seen possessed a very poor imitation of the true ehampaca odor. 

 Our investigations on this oil have not advanced very far, but some data 

 which may be of interest will be recorded. 



The yield appears to be over 0.2 per cent. The crude oil on standing separated 

 a large amount of a crystalline solid. This was filtered and an additional 

 quantity of it was again separated by the addition of ether, in which the solid 

 is quite insoluble. The remaining oil, after standing for some weeks in the 

 laboratory, continued to solidify until it gradually became semisolid. The second 

 solid which separated was amorphous and appeared to be resinous in nature. If 

 this semisolid extract is treated with 70 per cent alcohol, about half of it separates 

 in the form of the amorphous, brown, odorless body. This was filtered and the 

 filtrate concentrated at 40° in vacuo until a brown oil separated, which had a 

 very fine odor of ehampaca, and was readily soluble in 70 per cent alcohol or 



OAO 



stronger. Our oil had the following constants: Specific gravity, 0.9543; 



' 30° 



OAO 



refractive index, N . 1.4550; saponification number. l(i(). Another oil had 

 D 



30° 30° 



specific gravity. — , 1.020; refractive index. N rr_, 1.4830; saponification aumber, 



'30° D 



180. The second oil had the finer odor. The oils were too dark to permit of 

 determinations of the optical activity. My ehampaca oil is neutral. The recent 

 oil examined by Schimmel and Company 11 contained a considerable proportion of 



acid, especially of methyl ethyl acetic acid. 



» 



s /bill (1894), 1, 58. 

 9 Ibid. (1897), 1,11. 



10 Ibid. ( H)()7). 2. 



11 hoc. cit. 



