- 96 - 



duction. If the future proves that these results are crowned with 

 success, a new and important source of supply for the production of 

 a "turpentine oil" might thus be opened up, and at the same time 

 colonisation be facilitated. 



According to a method indicated by Lor en z 1 ) but not described 

 more in detail, it is possible to "extract" from pine wood "turpentine" 

 and rosin by means of distillation in vacuo, at a temperature at which 

 the wood is not decomposed. Both products are said to be of best 

 quality, and the turpentine especially "water white". 



Oil of Umbellularia californica. We have already on a 

 previous occasion referred to F. Tu tin's 2 ) experiments for clearing up 

 the constitution of umbellulone. The continuation of this work deals 

 in the first place with the reduction of umbellulonic acid 3 ). If this 

 acid is treated with sodium and alcohol, there is formed, with ring- 

 disruption and addition of two atoms hydrogen, a hydroxy acid with a 

 side-chain. This-, acid yields a lactone of the b. p. 246 to 248 , and 

 is oxidised by permanganate in the presence of an excess of alkali, 

 into acetic acid and isopropyl succinic acid. As has been shown at 

 the time, umbellulonic acid must contain either a methyl pen tarn ethylene, 

 or a dimethyl tetramethylene ring. A hydroxy acid which on subsequent 

 oxidation yields acetic acid and isopropyl succinic acid, can only 

 originate from the ketonic acids: — 



,CH.(CH 8 ). CH 2 



COOH.CH< 



-CH 2 CH.CO-CH 3 



I. 



/C(CH 3 ) 

 COOH.CH( XCH-CO-CH, 



\CH 2 — / 



II. 



and would correspond to the formula 



CH 3 • CHOH • ;CH 2 • CH 2 • CH(COOH) , CH(CH 3 ) 2 , 



i. e. it would be a (3-hydroxy-a-isopropyl caproic acid. Now, as has 

 previously been proved, formula II belongs to pinononic acid. For 

 this reason, only formula I can apply to umbellulonic acid, and further, 

 for umbellulone itself the formula previously drawn up: — 



*) Oil, Paint and Drug Reporter 69 (1906), 38. Accord, to Zeitschr. f. angew. 

 Chem. 20 (1907), 626. 



2 ) Journ. chem. Soc. 89 (1906), 1104; Report October 1906, 79. 



3 ) Ibidem 91 (1907), 271. 



