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Methyl heptyl ketone: Methyl nonyl ketone: 
Boiling point 194,5° to 195,5° Boilingpoint 2 2 9°to 2 33°(759mm), 
(763 mm). „ of the ketone regenerated 
Specific gravity d"^ 0,8296. from the^semicarbazone 231,5° 
Melting point of the semicarbazone ^3^,5 (7^^ mm). 
119° to 120° Specific gravity d^ 0,8263. 
Melting point of the semicarbazone 
122°. 
Valeric acid, present in the oil perhaps as ethyl ester^ was found 
on saponification of a fraction boiling from 165° to 170°. 1-Pinene 
was contained in the portions of the same boiling point, limonene and 
cineol in the fractions boiling from 170° to 185°. The presence of 
this hydrocarbon was proved by the nitrosochloride and the latter's 
nitrol piperidide. The two last-named bodies could be identified by 
the tetrabromide (m. p. 103°) and the iodol derivative (m. p. 114° 
to 115°) respectively, and by the hydrobromide of cineol (m. p. 55° 
to 56°). From the saponification liquors of the fractions boiling 
above 185°, an acid was obtained which distilled below 120°, and 
which was recognised as acetic acid by the analysis of its silver salt. 
Special interest is also attached to the presence of methyl heptyl and 
methyl nonyl carbinols in oil of rue, the secondary alcohols produced 
by Mannich and by Houben from the corresponding ketones. The 
authors succeeded in detecting the bodies in the fractions of the 
boiling points 190° to 200° and 210° to 235° respectively. The 
physical constants of the compounds are as follows : 
Methyl heptyl carbinol: Methyl nonyl carbinol: 
Boilino- point IQ=^° to 106^ (obtained from the acetyl compound of 
^ r 1 1 the crude carbinol) 
„ of the carbmol purified by 
the acetyl compound 198° to Boiling point 231° to 233°. 
200° (765 mm). Optical rotation ajy — 1° 18' 
Specific gravity d ^-f-^ 0,8273 (25 mm). 
Optical rotation — 3° 44^ 
(50 mm). 
The corresponding acetates boil at 213° to 215° and 245° respectively. 
Elementary analysis, and the formation of the ketones of the 
corresponding boiling points on oxidation of the carbinols with chromic 
acid, prove that the two products may be considered as methyl heptyl 
carbinol and methyl nonyl carbinol. 
The oil passing over between 250° and 320° has a blue colour 
and a herb-like odour. The ketone content, according to the authors, 
amounts to 80 per cent., the content of alcohols to about 10 per cent. 
