— 134 — 



The fruit of X. piperitum had been distilled by us many years pre- * 

 viously and at that time (Report October 1890, 61) we also made a brief 

 reference to the oil. A small sample of the fruit distilled at that time 

 was still available and this we have again submitted to botanical exami- 

 nation, as a result of which we have confirmed its derivation from 

 X piperitum. 



The oils obtained from Xanthoxylum Aubertia, D. C, and from X. alatum, 

 Roxb., to which we have briefly referred in previous Reports 1 ), have been 

 thoroughly investigated by Semmler and Schossberger 2 ). They found the 

 first-named oil to contain an aliphatic terpene, related to ocimene and 

 alloocimene, and possessing the following properties: d 2 oo 0,8248, « D + 30°, 

 n D 1,49775. The high-boiling fractions of the oil contained a hitherto un- 

 known, monocyclic sesquiterpene, to which the authors gave the name of 

 evodene (b. p. 119 to 123° at 9 mm.; d 20 o 0,8781 ; « D — 58°; n D 1,49900). 

 Semmler and Schossberger also showed the oil to contain from 40 to 60% 

 methyleugenol, which they identified from its oxidation-product, veratric 

 acid (m. p. 180 to 181°). After being heated with amylalcoholic potash 

 liquor the refraction of the methyleugenol-fraction was considerably higher 

 than before, from which follows that the oil contains methyleugenol and 

 not methyKsoeugenol. The fractions with the highest b. p. contained phlor- 

 acetophenone dimethylether 3 ) a body of which the presence in oil of Blumea 

 balsamifera was demonstrated in our laboratory some time ago 4 ). 



In the oil of Xanthoxylum alatum the authors discovered a terpene 

 which they call xanthoxylene 5 ), but which is perhaps identical with Z-sabinene. 

 This terpene yields a monohydrochloride, b. p. 83 to 87° (10 mm), d 20 o 0,959, 

 « D — 11°, n D 1,4824; reduction of the latter with sodium and alcohol giving 

 rise to a hydrocarbon Ci Hi 8 with the following constants: b. p. 52 to 58° 

 (9 mm.), d 20 o 0,8275, « D — 17°, n D 1,4582. When ozonised, xanthoxylene 

 forms a ketone of which the semicarbazone has b. p. 123°, whereas the 

 m. p. of the sabinene ketone semicarbazone is 141°. Other constituents 

 of the oil are phloracetophenone dimethylether and also perhaps cuminic 

 aldehyde. The phloracetophenone dimethylether separates out from the 

 oil at ordinary temperature in the form of a solid mass. This ether was 

 characterised by its monobromide (m.p. 187°), its methyl derivate (m. p. 103°), 

 and its acetyl derivate (m. p. 107°). 



Ylang-Ylang Oil. Generally speaking the trade in ylang-ylang oil 

 has been exceedingly flat, although the regular supplies of our "Sartorius^ 



>) Report April 1907, 105; October 1910, 147. 



2 ) Berl. Berichte 44 (1911), 2885. 



3 ) As regards characterisation see below. 



4 ) Jonas, Report April 1909, 147. 



5 ) The name "Xanthoxylene" has already been introduced by Stenhouse on a previous 

 occasion, obviously for the same terpene. [Pharmaceutical Journ. I. 17 (1857), 19; Liebigs 

 Annalen 104 (1857), 235; see also previous page. 



