* cc 
Recently, y. pate ‘dad U. Kehr! 2) have Road 15 per cent. citronellal to be 
nt in the oil, nothing, however, appearing in the abstract available as to the method 
EP idenuheation.: The ‘oil was colourless, mobile and smelled of citronella oil. 
8511; [@]p200-+ 45.459; acid v. 1.35; ester v. of the aldehyde-free oil 18.78. The 
Idehydes contained principally terpenes and yielded with nitrous acid a nitrite, 
p. 203 to 2049; [e], + 159. 9°, On oxidation with potassium permanganate and 
subs equent treatment with, acids it yielded a substance - ‘smelling of cuminaldehyde, 
- semicarbazone of which showed a m. p. of 203 to 204°, agreeing with that of 
ahydrocuminaldehyde prepared from 6-phellandrene in the like manner. However, 
‘@-phellandrene isolated by- Wallach from the oil of Phellandrium aquaticum is dextro- 
ees otatory and yields a levorotatory nitrite. Hence it is probable that xanthoxylum oil 
contains lzvorotatory 8-phellandrene, whose rotation appears to be inversed cue to 
‘the e Pe: of a dextrorotatory Ernore. 
Oa 
= ye 
<> 
@ Mt Paced padiut, Oil, pees: In addition to the numerous ; components of japanese 
. Pe eppermint oil, we have recently found a body hitherto unknown, the , y-hexenol ester 
0 - phenylacetic acid. The ester is remarkable by its strange, most lasting smell, and 
0 ccurs in the fractions boiling between 250 and 310°. On. Saponifying these fractions 
wit alcoholic potash, phenylacetic acid and hexylene alcohol result. The latter, on 
~ clos e investigation, was not identical with the «, 6-hexenol such as found in the green 
4 eaves of numerous plants by Curtius and Franzen, but revealed itself as B, y-hexenol 
_ CH; - CH, - CH: CH - CH, - CH.OH. The position of the double linking was manifested 
, by the results of oxidation, potassium permanganate leading to propionic acid, and 
Riek omic acid to 4, @-hexylenic acid. The ‘latter appeared, by transposition OF they 
double bond on ‘saponification, in accord with Fittio’s observations, from the hexenyl 
‘jamie . 
_ ester of 2, y-hexylenic acid formed primarily by oxidation. 
By y-Hexenol has the following. constants: — b, p. 55 to 56° (9 mim. iy 155, fe 156° at : 
mean atmospheric pressure; d150 0.8508; nee 0°10’; np200 1.48030. It-adds two atoms 
f, bromine. The smell reminds, in great dilution, of grass and fresh green leaves. 
os The following Bales were prepared from the hexenol from Japanese pepper- | 
cori it int oil: — } 
- Hexenyl eyes CusHigOo. B. p. 135 to. “136° (4 ual 299° on mm.); 
—  dhts0 1.000; @p -E. 0; npa90 1.49810. | : 
ey Hexeny! benzoate CisHigO2. B. i. 134 to 135° We mm); diso 1.0083; Beg: 
-——— pe9o 1.50560. : 
--—- Hexenyl- acetate CsH,,0>. ~—=B. p. 76 to 76° (23 mm.) ; ai 0.9077: Oy ey 
ee “Hyogo 1.42355. 
__Hexenyl formiate C;Hi202. B. p. 66° (35 mm.); \docogiay- ay + 0, Mowe “49685. 
-__—-Hexeny! «-naphthylurethane CizHioO.N, m. p. 70 to 71°. 
_ Hexenyl acid phthalate Cis Aig On, ligatd, yielding a well- crystallizing silver salt 
melting at 126°. ) 
ga this connection, we report on the hess, performed by us some. time 
oy the pie Goal corresponding to the above-mentioned a, 6-hexylene' alcohol, the 
‘at 
os 1) Report October 1890, 61. For later 4) SN, see Report October 1916, 41.. — 2) Yakugakuzasshi 
<a ») No. 415; Apotheker Zig. 32 wer) 550. / 
~ 
