Commercial and scientific notes on essential oils. 81 



Our friends say that in Java only the seeds are distilled. The oil obtained in a 

 comparatively small quantity is not exported but consumed in the country. It is con- 

 sidered inferior to the American product, as it is said to contain less ascaridole. The 

 wormwood cultivation in Java is rather difficult, as the seeds do not ripen at the same 

 time. The plant itself remains low and herbaceous. Plantations on a large scale have 

 been abandoned, as it was recognized that it would be impossible to compete with 

 the United States under normal conditions. 



Chenopodium herb Oil. — As is known, the American wormseed oil is distilled from 

 the seeding plant of Chenopodium ambrosioides, L., var. anthelminticum, Gray. We had 

 an opportunity of late to distil the herb by itself and shall here report on our experience. 



Fresh chenopodium herb, without seeds, yielded 0.0057 per cent, of an olive-green 

 oil showing the following constants, di 5 o 0.8552, « D ~M°> n D20 o 1.48141, acid v. 2.7, 

 ester v. 28.9, soluble in 5 vols, and more of 90 per cent, alcohol with slight opalescence. 



From a second sample of herb, just beginning to seed, 0,034 per cent, of a brown 

 oil were obtained, which had a higher specific gravity and a higher index of refraction 

 and dissolved a little better than the one before mentioned: di 5 o 0.8795, « D + 1°15', 

 n D a>o 1.48403, soluble in 1.4 vols, and more of - 90 per cent, alcohol. 



The extremely feeble odour was remarkable with both oils. They lacked almost 

 completely the typical smell of ascaridole, so that it is to be supposed that they con- 

 tained very little of this essential constituent. This would account perhaps for the 

 low specific gravity and the insufficient solubility. It is remarkable too that the oils 

 were dextrorotatory. 



We are unable so far to explain these abnormalities. It is questionable whether 

 they are only due to the absence of seeds, or whether the fact that the herb was 

 grown in Germany, under conditions of climate and soil differing from those in America, 

 is responsible for them. 



Since some confusion exists as to the question to which constituent of the oil 

 the anthelmintic action is due, Th. A. Henry and H. Paget 1 ) undertook a re-examination 

 of the oil. Six samples of commercial oils were used, with the constants: — d|£ 0.9582 

 to 0.9723, [«] D i5o — 4.5 to — 6.8°. The oils were separated by distillation under 15 mm. 

 pressure into three fractions: — 1) b. p. below 84° (25 per cent.), 2) 84 to 104° (15 per cent), 

 3) 104 to 118° (55 percent), the residue (5 per cent.) being chiefly ascaridole glycol. 

 The first fraction consisted mainly of hydrocarbons, furthermore butyric acid (Ag-salt), 

 methyl salicylate (below 5 per cent; m. p. of the salicylic acid 156°; benzoate of the 

 ester, m. p. 83°). The hydrocarbons were «-terpinene (nitrosite, m. p. 155°), a new 

 Isevorotatory terpene (with the approximate constants: b. p. 177 to 178° [760 mm.], 

 d 16 o 0.847, [a] D150 — 57°, n D20 o 1.484; tetrabromide, m. p. 117°, inactive) and £>-cymene. 

 The second fraction contained hydrocarbons and ascaridole, the third consisted of 

 nearly pure ascaridole (b.p.108 to 110° [15 mm.], d 15 o 1.0120, [a] m5 o — 0.5°). 



According to the statements of the authors, sylvestrene, limonene, phellandrene, 

 safrole and camphor were absent. The new terpene, which could not be separated 

 from a-terpinene and />cymene, yielded on oxidation with potassium permanganate 

 acetic acid, isobutyric acid and a minute amount of a volatile acid, m. p. 117°, 

 crystallising in long, slender needles, but insufficient for examination. On oxidising 

 «-terpinene with potassium permanganate in acetone solution, the authors obtained 

 two optically inactive forms of a.^-dihydroxy-a-methyl-^-isopropyladipic acid (m. p. 203 



1 ) Journ. chem. Sod. 119 (1921), 1714. From a copy kindly furnished by the authors. 



