PHILIPPINE TBRPENES AND ESSENTIAL OILS, III. 99 



In addition to the a and j3 phellandrene above noted, there would 

 seem to be a higher boiling phellandrene in elemi resin, boiling point 



175° to 178° at 760 millimeters; specific gravity,^ =0.8375; N^^ = 



4 D 



30° 



1.4685 ; A 82.4. This phellandrene by the above treatment also 



gives the phellandrene nitrite melting at 131°. fi phellandrene on oxida- 

 tion with dilute potassium permanganate gives the aldehyde, phellandral, 

 with an odor like cuminol, while this is not obtained with my a phellan- 

 drene. It is evident that much more extensive study is necessary to 

 clear up the diiBculties noted here and I will again take up this subject 

 when I have obtained the two standard phellandrenes, the a from bitter- 

 fennel oil, Fwniculum vulgare Mill, and the j8 from waterfennel oil, Phel- 

 loMdrium aquaticum L. for comparative purposes. Semmler ^° oxidized 

 phellandrenes with dilute potassium permanganate and the first products 

 which he obtained he subsequently oxidized with lead superoxide, thus 

 separating quantilively 1-isopropyl succinic acid from a phellandrene, and 

 from /3 phellandrene a isopropyl glutaric acid, both being crystalline 

 compounds easily identified. Semmler does not give the exact condi- 

 tions under which he made these oxidations. I have oxidized my a 

 and j8 phellandrenes with potassium permanganate iinder various con- 

 ditions, but have never been able to obtain quantitative yields of these 

 aeids.^'^ Unless quantitative yields can be obtained, it is evident that 

 the method is not of much value in deciding the difficult question as to 

 whether a sample of a phellandrene contains a small quantity of another 

 phellandrene. 



THE BESIDUE FEOM THE DISTILLATIOK OF ELEMI. 



From 12 to 18 per cent of terpenes are obtained by the distillation 

 of elemi in vacuo, and from 12 to 15 per cent of a higher boiling oil, 

 of which one of the constituents has recently been proved by Semmler ^- 

 to be elemicin, (allyl-l-trimethoxy-3,4,5-benzol). The distillation resi- 

 due, usually amounting to about 70 per cent of the elemi, is a light 

 brown, transparent, solid resin, with a brillant : fracture. This elemi 

 residue is completely and easily soluble in the cold in the following 

 solvents : Alcohol ; ether ; benzol ; petroleum ether ; ligroin ; xylol ; 

 eholoroform; amyl acetate; acetone; methyl alcohol; carbon tetra- 

 chloride; ethyl acetate; turpentine; amyl alcohol, and glacial acetic acid. 



•"Ber. d. deutschen chem. Ges. (1903), 36, 1749. 



" Kondakow (Jouni. f. prakt. Chem. (1908), n. s. 73, 42) has recently proved 

 that, contrary to the long accepted view, the phellandrene from Phellandrium 

 aquaticum is not an individual terpene, but contains over 20 per cent of pinene. 

 He announces a thorough investigation of the whole phellandrene ehemistrj'. 

 Kondakow's work throws grave doubt on the quantitative yields claimed by 

 Semmler for the oxidation of these terpenes with potassium permanganate. 



"Ber. d. deutschen chem. Ges. (1908), 41, 1768, 1918, 2183. 



