_ COMMERCIAL AND SCIENTIFIC NOTES ON ESSENTIAL OILS. 63: 
nitric acid becomes permanent. If the red solution is diluted and made alkaline with — 
_ sodium hydroxide, a dark-green coloration appears which is not absolutely permanent. 
_ The oxime (m. p. 107°) and the dimethyl! ether (m. p. 102 to 103°) could be prepared, and 
_ the proof deduced that in hydroxypzonol there is a monomethyl ether of the 2, 4, 6-tri- 
hydroxyacetophenone present. The position of the methoxy group (probably the para- 
_ position, pzonol gives quite similar reactions) could not be decided however with certainty. 
The red rosin of Xanthorrhea Preiss was also dissolved in alkali and subjected 
to steam distillation. Slightly over 1 percent. of a yellow strongly smelling oil passed 
_ over that at 20 mm. was separated into five fractions (110 to 155°, 155 to 165°, 165 
— to 185°, 185 to 200°, 200 to 210°). The small residue was Somewhat viscous and 
_ uncrystallisable. Fraction 3 contained chiefly pzeonol and a small quantity of a non- 
_ ¢rystallising oil. Fraction 4 proved to be hydroxypzonol. Fraction 5 was solid and was 
recrystallised from alcohol (m. p. 69.59). Probably a methoxydiphenyl ether was present, 
_ but an exact proof was not forthcoming. From fraction 1 a colourless oil was obtained 
_ by distillation 118 to 120° (20 mm.), whose identity with /-citronellol was established 
_ (silver salt of the citronellylphthalic ester acid; m.p. 125°). The higher fractions of 
' the raw oil had a mint-like smell, and it is to be assumed that isopulegol was present 
_ that had probably been formed from citronellal during the frequent distillations’). 
_ a Tee Ee 
Oil of Xanthoxylum ailanthoides.— Our note on the essential oil of the leaves 
of Xanthoxylum ailanthoides, Sieb. and Zucc. (Report October 1916, 62) is amplified by 
the following information from Raspe 8 Co.%), Kobe. The rutacea grows wild in Suruga 
_ in Idzu, on the island Oshina in Idzu and on the Liukiu and Ogasawara Isles. In 
. Chadesaacs the plant in named Ako. 
(a) Oil from old leaves (Dshukuyo-oil). Colgir orange yellow, smell and taste 
pleasant somewhat piquant. Yield 0.5 percent. Angle of Rotation is a, + 6.35°, not 
@, — 6.35° as stated in Journ. Soc. chem. Industry 34 (1915), 1270%). B.p. 200 to 240° 
_(ord. press). The oil formed many crystals on being shaken up with sodium bisulphite 
solution. On standing over night in ice-cupboard the whole formed a crystalline mass. 
The chief constituent methyl- n-nonylketone, was identified by the constants (b. p. about 
232°; diso0.8302; freezing point 10°), and by the semicarbazone (m.p.123°). At 14mm. the 
five following fractions were obtained from oil treated with sodium bisulphite solution: — 
65 to 80°, about 10 per cent. of the raw material, smell strongly of pinene; 80 to 90°, about 
30 per cent. of the raw material, smelt strongly of ketone, and consisted mostly of 
methyl-n-nonyl ketone; 90 to 100°; 100 to 120° and 120 to 130°. Methyl-n-heptyl 
ketone appeared also to be present in the oil. ; | 
(b) Oil from partly old leaves (Han-dshukuyo-yu). Colour bright yellow; angle ‘Oh y 
rotation is a) +5.75°, not —5.75°°%). The ketone content was pate tee greater than 
that of the oil from old leaves. 
_ -(e) Oil from fresh leaves (Shinga-yu). Colour S cflowiaiwecn odour ales saneee 
than that of (a), and (4). Angle of rotation ¢p ++ 6.63, not ¢p — 6.63?). 
| Yamakosho leaf Oil. — Angle of rotation of this oil is ae 18.8°4), not «— 18.8°, 
as stated in Journ. Soc. chem. Industry 34 (1915), 7270°). 7 
1) Cf. Report April 1909, 96. — 2) Y. Shinosaki, Report of the Industrial Laboratory (Kogyo Shikenjio) Tokyo, 
March 1916. Yakugaku Zashi 1906, 1095. — *) Cf. Report 1916, 62, — *) Y. Shinosaki, Report of the Industrial 
Laboratory (Kogyo Shikenjio) Tokyo, March 1916. Yakugaku Zashi 1906, 1095. — 5) Cf. Report 1916, 63. 
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