39 A-40.] 



TERPINEOL 



91 



and 1-linalool by the same reagent into 

 d-terpineol (Stephan, loc. cit.). 



Or from linalool through terpin hydrate 

 (see under dipentene [9; D]), which on 

 boiling with dilute mineral acid or with 

 acetic acid gives terpineol among other 

 products (Wallach, Ann. 230, 364). 



[B.] From geraniol [36] through 

 terpin hydrate (see under dipentene 

 [9; C]) and then as above (Stephan, 

 Journ. pr. Ch. [2] 6O, 244). Geraniol 

 is also converted by strong formic acid 

 at ordinary temperatures into terpinyl 

 formate in 10-12 days. Terpinyl ace- 

 tate is produced in small quantity from 

 geraniol by heating the latter to 60- 

 70 with acetic acid containing a little 

 sulphuric acid (Stephan, loc. cit.). 



NOTE : The liquid terpineol prepared on the 

 large scale by boiling terpin hydrate with 

 dilute acids contains a mixture of isomerides 

 among which, together with the natural i-ter- 

 pineol, is a terpineol (A 8>9 -terpen-i-ol) isomeric 

 with the foregoing natural and synthetical pro- 

 ducts (Schimmel's Ber. April, 1901 ; Stephan 

 and Helle, Ber. 35, 2147). 



[C.] From limonene [9] by the action 

 of silver or lead oxide on the hydro- 

 bromide, or by the action of acetic acid 

 containing sulphuric acid on the hydro- 

 carbon (Semmler, Ber. 28, 2189). 

 Both d- and 1-limonene give terpineol 

 by this method. 



Dipentene gives terpinyl acetate on 

 heating with glacial acetic acid to 100 

 (Bouchardat and Lafont, Comp. Rend. 



102 ; I 555); 



NOTE : It is not certain that the constitutional 

 formula given above expresses the structure 

 of all the synthetical terpineols obtained by 

 the foregoing processes. 



40. Cineole; Cajepntole; Eucalyp- 

 tole. 



CH, 



H 2 C CH a 



H,C V CH, 



C' 

 H 



NOTE : For constitutional formula see Wal- 

 lach, Ann. 291, 350. 



NATURAL SOURCES. 



The chief constituent of oil of worm- 

 seed from the flower heads and stalks 

 of Artemisia maritima and vars. (Kraut, 

 Jahresber. 1862, 460 ; Kraut and 

 Wahlforss, Ann. 128, 293 ; Hell and 

 Stiircke, Ber. 17, 1970; Wallach 

 and Brass, Ann. 225, 291). 



Occurs also in oil of Artemisia vulgaris 

 (Schimmelj Gildemeister and Hoff- 

 mann, p. 891); in oil of cajeput 

 (Wallach, loc. cit. 315) ; in niauli oil 

 (66 per cent., Bertrand, Bull. Soc. [3] 

 9, 435 ; Comp. Rend. 116, 1070) ; in 

 oil of Melaleuca acuminata (Schimmel's 

 Ber. April, 1892); and in oil of M. leuca- 

 dendron, var. lancifolia (Ibid.). 



Cineole has been found also in oil 

 from the leaves of Laurus nobilis (Ibid. 

 April, 1899); in American oil of 

 peppermint (Power and Kleber, Pharm. 

 Rund. 12, 157; Arch. Pharm. 232, 

 639); in camphor oil from Laurus 

 (Cinnamomum) campkora (SchimmeFs 

 Ber. Oct. 1888; Oct. 1902); in oil of 

 sage from Salvia officinalis (Wallach, 

 Ann. 252, 103) ; in oil of spike laven- 

 der (Bouchardat and Voiry ; see under 

 linalool [37]) ; in oil of lavender (traces) 

 (Schimmel's Ber. Oct. 1893), and in 

 Portuguese oil of lavender from Lavan- 

 dula pedunculata (Ibid. Oct. 1898). 



Occurs also in German oil of sweet 

 basil from Ocymum basilicum (Bertram 

 and Walbaum, Arch. Pharm. 235, 176 ; 

 SchimmePs Ber. April, 1897 : see also 

 Hirschsohn as quoted by Gildemeister 

 and Hoffmann, p. 860, note) ; in oil of 

 rosemary from Rosmarinus officinalis 

 (Weber, Ann. 238, 89) ; in oil from 

 the root of the 'Chinese galangal/ 

 Alpinia officinarum (SchimmeFs Ber. 

 April, 1890; Schindelmeiser, Ch. Zeit. 

 26, 335), and from the root of Kaemp- 

 feria rotunda (SchimmeFs Ber. April, 

 1894) ; in oil of Bengal cardamom 

 from Amomum (Elettaria) aromaticum 

 (SchimmeFs Ber. April, 1897); in a 

 Camaroon cardamom oil from (?) Amo- 

 mum danielli (Ibid. Oct. 1897), and in 

 Malabar cardamom oil from Elettaria 

 cardamomum (Ibid. Oct. 1897; Parry, 

 Pharm. Rev. 9, 105). 



Cineole is contained also in oil of 



