90 



ALCOHOLS 



would therefore give citronellol on re- 

 duction (Harries and Schauwecker, loc. 

 tit.). 



NOTE : According to Bouveault citronellol 

 and rhodinol are isomerides (see for summary 

 Bull. Soc. [3] 23, 458 ; also under menthone 

 [129]). 



39. Terpineol; Terpilenol; Terpene 



Hydrate ; Menthenol ; 

 A 1 -8-Hydroxytetrahydrocymene ; 

 A^Terpen-S-ol. 



CH 3 

 H 2 C CH 



[38 B-39 A. 



H 2 C 



CH, 



V 



CH 3 .C(OH).CH S 



NOTE : For constitutional formula see Wag- 

 ner, Ber. 27, 1652. 



NATUEAL SOURCES. 



i-Terpineol (and acetate) occurs in 

 oil o cajeput from Melaleuca leucaden- 

 dron and var. minor (Voiry, Comp. 

 Rend. 106, 1538; Bull. Soc. [2] 50, 

 108), and in niauli oil from Melaleuca 

 viridifolia, New Caledonia (Bertrand, 

 Bull. Soc. [3] 9, 433 '> Comp. Rend. 

 116, 1070); in oil of Ceylon cardamom 

 from Elettaria cardamomum, var. major, 

 Smith (Weber, Ann. 238, 98) ; and in 

 oil of Malabar cardamom (d-terpineol) 

 from M cardamomum (Schimmel's Ber. 

 Oct. 1897; Parry, Pharm. Journ. 9, 



105); 



Oil of sweet marjoram from Origanum 

 majorana contains d-terpineol (Biltz, 

 Ber. 32, 995). Terpineol is contained 

 in the oil of Lindera sericea, the ' kuro- 

 moji' oil of Japan (Kwasnik, Arch. 

 Pharm. 23O, 265); in the Japanese 

 ' kesso ' oil from the root of Valeriana 

 officinalis, var. angustifolia (Bertram and 

 Gildemeister, Arch. Pharm. 228, 483) ; 

 and in oil of fleabane from the N. 

 American Erigeron canadensis (Kremers 

 and Hunkel, Pharm. Rund. 13, 137). 



1-Terpineol is probably present in 

 lemon-grass oil (Tiemann, Ber. 32, 835). 



d-Terpineol is contained in oil of lovage 

 from the root of Levisticum officinale 

 (Schimmel's Ber. April, 1897, p. 27, 

 and Oct. 1897, p. 9, note). The oil 

 from Calif ornian bay ( Umbellitlaria cali- 

 fornica) contains a mixture, 'terpinol/ 

 of which terpineol is one of the con- 

 stituents (Stillmann, Ber. 13, 630; 

 Wallach, Ann. 230, 251). Oil of Gar- 

 denia contains terpineol (Parone, Boll. 

 Ch. Farm. 41, 489; Ch. Centr. 1902, 



2, 703)- . 



The oil of the rind of the sweet 

 orange (see under linalool [37] : Stephan, 

 Journ. pr. Ch. [2] 62, 523 and Schim- 

 mel's Ber. Oct. 1900) contains 39-4 per 

 cent, of d-terpineol. Oil of Mexican lina- 

 loe (see under geraniol [36] : SchimmeFs 

 Ber. Oct. 1900; Ch. Centr. 1900, 2, 970) 

 contains terpineol. So also does man- 

 darin oil from Citrus madurensis (Schim- 

 meFs Ber. Oct. 1901 ; Ch. Centr. 1901, 

 2, 1007). Oil of spike from Lavandula 

 spica may contain terpineol (Bouchardat, 

 Comp. Rend. 117, 53; 1094). 



1-Terpineol is contained in the oil of 

 Asarum canadense (Power and Lees, 

 Proc. Ch. Soc. 17, 21O; Trans. 81, 65). 

 Camphor oil from Laurus camphora pro- 

 bably contains terpineol (Schimmel's 

 Ber. Oct. 1888). d-Terpineol is pre- 

 sent in oil of lemon (Schimmel's Ber. 

 Oct. 1902; Ch. Centr. 1902, 2, 1207), 

 in French neroli oil (Ibid.}, and in petit- 

 grain oil from Paraguay (Ibid.). 



NOTE : No method for resolving inactive 

 terpineol into its optical isomerides is at 

 present known. 



SYNTHETICAL PROCESSES. 



[A.] \-Linalool [37] gives d-terpineol 

 and its acetate with geraniol on heating 

 with acetic anhydride to 150-160 

 (Schimmel's Ber. April, 1898 ; Stephan, 

 Journ. pr. Ch. [2] 68, 109). The 

 crude product thus obtained is the 

 ' licarhodol ' of Barbier (see under 

 geraniol [36 ; B]). 



Or linalool on treatment (below 20) 

 with acetic acid containing \ per cent, of 

 sulphuric acid gives 45 per cent, of its 

 weight of d-terpineol and 10 percent, of 

 geraniol (Stephan, loc.cit.}. d-Linaloolon 

 treatment with strong formic acid below 

 2O is largely converted into 1-terpineol, 



