64 



directions, making a very tine exhibit. The melting point of tlie pure crystals 

 was gi° C. On analysis the following results were obtained: — 



0"2273 gram gave 0-2385 gram H.,0, and 0-6756 gram CO,. 



H = 11-66 and C = 81-07 P^r cent. 

 C,-H,,P requires H = 11-71 and C = 81.08 per cent. 



A second analysis gave corresponding results. A sesquiterpene alcohol was thus 

 indicated. 



The crystals were readily soluble in alcohol, even \\hen this was somewhat 

 dilute ; they were also soluble in ether, in petroleum ether, in glacial acetic acid, 

 in chloroform, in acetic ether, and other organic solvents. The crystals were 

 Ijevo-rotatory, and 0-5 gram dissolved in 10 c.c. alcohol, had a rotation in a i dcm. 

 tube — i-45°. the specific rotator}- power from this is [«]„ = — 29°. 



\\'hen boiled with acetic anh\-dride in the usual wav, onlv a liquid acetate 

 was obtained. 



When the crystals were heated with zinc chloride at 170-180° C, water 

 added when cold, and the solution steam-distilled, a blue oil was obtained; 

 this was at first a little green, but it became bright blue on standing some hours. 

 The blue colour slowly faded if the air had full access. 



When the crystals were gently heated with phosphoric anhydride, the colour 

 changed to bright red and purple. \Mth concentrated sulphuric acid the crystals 

 were dissolved easih' to a vellow colour which soon became orange, and on 

 standing, to a pink colour on the edges. \\'hen the dehydration was somewhat 

 complete, a thick liquid separated. With strong nitric acid the crystals became 

 an oily mass, which after a short time were deep crimson, and purple to violet on 

 the edges, the colour eventually fading away. 



The above results show the crystallised portion of the oil of Callitris wood 

 to be the sesquiterpene alcohol, Guaiol. Guaiol was originally isolated from the 

 oil of guaiac, or guaiacum, which was first prepared commercially by Schimmel 

 & Co., and brought into commerce as a jjerfumery oil. This oil was distilled 

 from the wood of Bulnesia sarmienti, l.or., a tree belonging to the N.O. 

 Zygophyllaceae, which is known as " Palo balsamo," in Argentina, and supplied 

 under that name*. .A portion of this substance was kindly sent to us by 

 Messrs. Schimmel & Co., and it gave identical reactions with our Guaiol. 



The timber of the " Stringybark Pine," Callitris Macleayana, was treated 

 similarly to that of C . glauca, and a srmi-cr\stallinr prnrlurt obtained by steam 

 di<till;ifioii. Tlii^ was of a deep red colour, and \n odour was less distinctive 



•Schimmel and Co.'s Reports .\pril, iSoR, p. 28, aiul Octobi^r, 1X98, p. J9. Also Gildemeister& HoMmann , 

 "The Volatile Oils," p. .\ii. 



