208 R. T. BAKER AND H. G. SMITH. 



He suggests the following formula for farnesol, which it 

 will be seen is an extension to the geraniol grouping : — 

 OH 3x 



>0 : CH.CHo.CH 2 .C : CH.CH 2 

 OH 3 / 



OH, 



CH 2 .0:OH.CH 2 OH. 

 OH, 



3 



Harries and Haarman (Ber. 1913, p. 1737) have also 

 investigated the structure of farnesol by oxidation with 

 ozone, and agree with the above formula. 



It will be seen that farnesol does not contain an asym- 

 metric carbon atom, and is thus inactive. The alcohol in 

 the leaf oil of Melaleuca Smithii is dextro-rotatory, so that 

 the molecule contains an asymmetric carbon atom, and 

 thus must be a different substance to farnesol. The 

 characters recorded for nerolidol (above) appear to agree 

 more closely with those so far obtained with the alcohol 

 from the oil of this Melaleuca. The difference in molecular 

 structure between these substances may perhaps correspond 

 to that between geraniol and linalool, as a tertiary carbon 

 atom appears to be present, but considerable work is 

 necessary to be carried out with this alcohol before its 

 characteristics and its molecular structure can be 

 ascertained ; and we know very little, as yet, about the 

 molecule of nerolidol. 



We propose the name melaleucol for the dextro-rotatory 

 aliphatic sesquiterpene alcohol which occurs in the leaf oil 

 of this species of Melaleuca. 



Melaleucol is an almost colourless, slightly viscous oil, 

 with a weak, but somewhat pleasant odour. When dis- 

 solved in chloroform, or in glacial acetic acid, it takes up a 

 large amount of bromine, and is thus highly unsaturated. 

 This was also shown by the permanganate reaction. 



So far, no satisfactory combination with this alcohol has 

 been obtained, so that it has not yet been isolated in a 

 perfectly pure condition. When freshly extracted from 



