— 51 — 
temperature. Calaminthone yields as products of reduction menth(jne 
and menthol. With the exception of the position of the double 
linking which still remains to be ascertained, the constitution of this 
ketone has thus been determined with a fair amount of certainty. 
Matico Oil. Fromm and van Emster have recently published 
the results of the examination of a matico oil which originated from 
our factory and which was marked 'heavy portions' 2). This oil had 
the specific gravity 1,123 15°? differed in a marked degree from 
the oil hitherto examined, by the total absence of asarone and matico 
camphor. About 70 to 75 per cent, passed over between 275° and 
289*^, and contained chiefly only one body, which the authors call 
matico ether, and whose formula was found as C^4^iiis^4:' represents 
a bright-yellow faintly fluorescent oil, volatilising with water vapour 
only with difficulty, which has the boiling point 282° to 285°, and the 
specific gravity 1,136 (at 17°). When kept for a prolonged time in 
a dark place matico ether acquires a brown colour, an occurrence 
which does not take place when the substance is left standing in sunlight. 
Chemically matico ether behaves very indifferently. It is attackeci 
by hydriodic acid with loss of pure methyl iodide. The methoxyl 
determinations after Zeis el correspond to the value of two methoxyl 
groups. W^hen oxidised with a 5 per cent, solution of potassium per- 
manganate, the new body yields a neutral product of the melting 
point 88^, and an acid having a melting point of 138°. The former 
is an aldehyde of the formula C^^II-^qO^, and is called by the authors 
matico aldehyde. With silver oxide it is oxidised into the acid C^lo -^10 
maticoic acid. This is identic with the acid of the melting point 138° 
obtained direct by oxidation of matico ether. 
From the portions of matico oil boiling above 275°, there can be 
isolated by oxidation with a 2 per cent, solution of potassium per- 
manganate, in addition to matico aldehyde, also homomaticoic acid, 
whose melting point lies at 96^, and to which the formula Ci^iii2^6 
belongs. Like matico aldehyde and maticoic acid, this acid also con- 
tains two methoxyl groups. 
If the fraction of the examined oil which boils above 275° (dissolved 
in glacial acetic acid, chloroform, petroleum ether, or carbon disulphide) 
is mixed with an excess of bromine, the bromide Cj^iHj3 03Br3 is 
obtained, which melts at 116°. 
^) Berliner Berichte 35 (1902), 4347. 
^) We would point out, that it was here not a question of a normal oil, but 
only of the portions which during distillation had separated out on the bottom of 
the receiver, and which therefore were heavier than water. We have observed that 
oils whose distillation-material contains a large admixture of fruit heads, are com- 
paratively richer in heavy constituents than those which have been distilled from 
leaves only. 
4" 
