This sesquiterpene is obtained, together with isoprene and dipentene, upon the destructive distillation of caoutchouc or gutta percha.4) Thus, 5 ko. of para caoutchouc5) yield about

1) Liebig's Annalen 271 (1892), 292.

2) Compt. rend. 138 (1904), 1228.

3) Arch, der Pharm. 245 (1907), 208.

4) Williams, Jahresber. d. Chem. 1860, 495; comp. also Beilstein, Hand-buch d. org. Chem. 3rd ed., vol. 3, p. 538.

5) G. Bouchardat, Bull. Soc. chim. II. 24 (1875), 108. Comp. also A. Bouchardat, Liebig's Annalen 27 (1838), 30; Himly, ibidem 27 (1838), 40.

250 g. isoprene, 2000 g. dipentene and 600 g. heveene.1) To a smaller extent polyterpenes also are formed. Bouchardat records 255 to 265° as boiling temperature. With hydrogen chloride a readily decomposible monhydrochloride C16H24HC1 is stated to be formed.

In the tables which follow, those sesquiterpenes are mentioned which have been found in volatile oils and of which some of the physical constants are known and which do not appear to be identical with known, well characterized sesquiterpenes.

Sesquiterpene from

B. p.

d

aD

nD

Remarks

Ageratum oil2)

260°

-

-

-

-

Angelica root oil3)

240 to 270°

-

-

-

-

Angostura bark oil4) (Galipene)

255 to 260°

0,912 (19°)

+- 0°

1,50513

With hydrogen chloride, readily decomposible liquid products are formed.

Oil from the leaves of Amorpha fruticosa5)

250 to 260°

0,916 (15°)

-

1,50652

The presence of cadinene has also been proven.

Oil from the rhizome of Aralia nudicaulis

(Araliene)6)

260 to 270°

0,9086 (20°)

-7 to -8° (benzene solution)

1,49936

-

Boldo leaf oil7)

265 to 275°

-

- 7°

-

-

Calamus root oil8)

255 to 258°

0,942

(0°)

0,9323

(20°)

-

-

-

1) The name heveene was suggested by Bouchardat from the name of the plant Hevea guianensis which yields the caoutchouc.

2) van Romburgh, Report of Schimmel & Co. April 1898, 53.

3) Ciamician and Silber, Berl. Berichte 29 (1896), 1811.

4) Beckurts and Troeger, Arch, der Pharm. 236 (1898), 397.

5) Pavesi, Estratto da//' Annuario della Soc. Chimica di Milano 11 (1904), 3; Estratto da/ "Rendiconti" del R. 1st. Lomb. disc, e lett. (II.) 37 (1904), 487; Report of Schimmel & Co. October 1904, 9.

6) Alpers, Americ. Journ. Pharm. 71 (1899), 370.

7) Tardy, Journ. de Pharm. et Chim. VI. 19 (1904), 132.

8) Kurbatow, Liebig's Annalen 173 (1874), 4; comp. Schimmel's Bericht April 1889, 7 and Apotheker Ztg. 21 (1906), 987.

Sesquiterpene from

B. p.

d

«D

nD

Remarks

Oil of Carlina acaulis1) (Carlinene)

139 to 141° (20 mm.)

0,8733 (22,8°)

-

1,492

-

Cascarilla oil'2) I

178 to 181° (100 mm.)

255 to 257° (760 mm.)

0,911 (20°)

[a]„ + 23,49°

Neither of these sesquiterpenes yielded a solid

Cascarilla oil II

185 to 190° (100 mm.)

260 to 265° (760 mm.)

0,924 (20°)

[a]d + 7,36°

hydrochloride, bromide or nitrosite.

Ceylon Citronella oil3) (heavy sesquiterpene)

170 to 172° (16 mm.)

272 to 275° (760 mm.)

0,912 (15°)

+ 5° 50'

-

Crystalline derivatives were not obtained.

Conima resin oil4) (Conimene)

264°

-

-

-

-

Cryptomeria oil5) (Suginene)

-

0,918

[«]D-10°34'

-

Cadinene also is found in the oil. Suginene produces liquid addition products with

2 mol. of hydrohalogen.

Cubeb oil6)

262 to 263°

-

lasvogyrate

-

The sesquiterpene fraction consists chiefly of cadinene.

Oil from Eucalyptus haemastoma, also from several other eucalyptus oils7)

(Aromadendrene)

260 to 265°

0,9249 (19°)

-

-

-

Fire weed oil8)

240 to 310°

-

-

-

Adds 1 mol. of hydrogen chloride.

1) Semmler, Chem. Ztg. 13 (1889), 1158.

2) Thorns, Apotheker Ztg. 14 (1899), 562; Fendler, Arch. der Pharm. 238 (1900), 688.

3) Schimmel's Bericht October 1899, 19.

4) Stenhouse and Groves, Liebig's Annalen 180 (1876), 253; Journ. chem. Soc. 29 (1876), 175.

5) Kimura, Berichte d. deutsch. pharm. Ges. 19 (1909), 369.

6) Wallach, Liebig's Annalen 238 (1887), 18.

7) H. G. Smith, journ. and Proceed. Royal Soc. of N. S. W. 35 (1901); Report of Schimmel & Co. April 1902, 41.

8) Beilstein and Wiegand, Berl. Berichte 15 (1882), 2854.

Sesquiterpene from

B. p. d

!

aD

nD

Remarks

Galangal oil1)

230 to 240° [0,932

- 27° 12'

1,4922

With hydrogen chloride it yields a dihydrochloride melting at 51°.

Gurjun balsam oil2) (Gurjunene)

115 to 118° (7 mm.)

0,9207 to

0,9247

05°)

- 35° up to-130°

1,50252 (20°)

Crystalline derivatives were not obtained.

Hemp oil8) (Cannabene)

256 to 258°

0,9289 (0°)

[a]D- 10,81°

-

With hydrogen chloride a solid hydrochloride results.

Hemp resin oil4)

258 to 260°

0,898 (18°)

[«]d-8,6°

-

-

Kesso root oil5)

260 to 280°

-

-

-

A solid hydrochloride could not be obtained.

Laurel berry oil0)

abt. 250°

0,925 (15°)

- 7,227°

-

-

Lavender oil7)

130° (15mm.)

-

-

-

-

Oil from Lepto-spermum Liversidgei8)

-

0,9024 (15°)

-

1,5052 (16°)

-

Lignaloeoil9), Mexican

130 to 140° (10 mm.)

-

-

-

Adds four atoms of bromine.

Oil from Nardostachys /atamansi10)

250 to 254°

0,932 (15°)

-

-

-

1) Schindelmeiser, Chem. Ztg. 26 (1902), 308.

2) Unpublished observation made in the laboratory of Schimmel & Co.

3) Valenta, Gazz. chim. ital. 10 (1880), 479 and 11 (1881), 191; Berl. Berichte 13 (1880), 2431 and 14 (1881), 1717.

4) Wood, Spivey and Easterfield, Journ. chem. Soc. 69 (1896), 539.

5) Bertram and Gildemeister, Arch, der Pharm. 228 (1890), 486.

6) Bias, Liebig's Annalen 134 (1865), 1.

7) Semmler and Tiemann, Berl. Berichte 25 (1892), 1187.

8) Baker and Smith, Journ. and Proceed. Royal Soc. of N. S. W. 1906; Report of Schimmel & Co. October 1906, 46.

9) Barbier and Bouveault, Compt. rend. 121 (1895), 168.

10) Y. Asahina, Journ. pharm. Soc. of Japan 1907, 355; Report of Schimmel & Co. October 1907, 65.

Sesquiterpene from

B. p.

d

«D

nD Remarks

Patchouli oil1)

I. Sesquiterpene

264 to 265° (760 mm.) 59 to 96°

(3 to 4 mm.)

0,9335 (15°)

- 58° 45'

-

-

II. Sesquiterpene

273 to 274°

0,930 (15°)

+ 0°45'

-

-

Oil from Pittosporum undulatum2)

263 to 274°

0,910 (15°)

+ 0°

1,5030 (20°)

-

Sage oil3)

264 to 270°

0,9072 (24°)

+ 3° 14'

-

-

Sandarach resin oil4)

260 to 280°

0,9386 (15°)

-

1,5215

No crystalline derivatives could be obtained with hydrogen chloride, nitrosyl chloride and nitrogen oxide.

Valerian oil5)

160 to 165° (50 mm.)

-

- 9,2°

-

-

Vetiver oil") (Vetivene)

262 to 263°

(740 mm.)

135° (12mm.)

0,932 (20°)

+ 18° 19'

-

Adds 4 atoms of bromine.

Winters bark oil7) (Winterene)

260 to 270° (265°)

0,9344 (13°)

+ 11,2°

-

The hydrochloride is liquid.

Oil of European Wormseed8)

255°

0,9170

-

-

-

1) von Soden and Rojahn, Berl. Berichte 37 (1904), 3353.

2) Power and Tutin, Journ. chem. Soc. 89 (1906), 1083.

3) Sugiura and Muir, Pharmaceutical Journ. III. 8 (1877), 191, 994; Journ. chem. Soc. 1877, II. 548; Journ. chem. Soc. 37 (1880), 678.

4) Henry, Journ. chem. Soc. 79 (1901), 1149.

5) Oliviero, Compt. rend. 117 (1893), 1096; Bull. Soc. chim. III. 11 (1894), 150; 13 (1895), 917.

6) Genvresse and Langlois, Compt. rend. 135 (1902), 1059.

7) Arata and Canzonari, Anales de la Sociedad Cientifica Argentina. According to Arch. der Pharm. 227 (1889), 813.

8) Report of Schimmel & Co. October 1908, 69.

Of the artificially prepared sesquiterpenes that have not been identified with any of the well characterized ones, the following may be mentioned:

Sesquiterpene

B. p.

d

aD

nD

Remarks

Caryophyllene dichlor- hydrate of the m. p.

69 to 7001)

-

0,9191 (20°)

- 35,39°

1,49801

-

Cedrol2) (Cedar camphor resp. cypress camphor)

263,5 to 264°

0,9367 (15°)

- 85° 57'

1,49798 (20°)

A small yield of nitroso- chloride, m. p. 100 to 102°, was obtained.

Cubeb camphor3)

-

-

-

-

This sesquiterpene is said to possess constants similar to those of the hydrocarbon found with cadinene in oil of cubeb.

Sesquiterpene alcohol from

Eucalyptus Globulus4) I. Sesquiterpene

102 to 103°

(6 mm.)

247 to 248°

(748 mm.)

0,8956 (15°)

- 55° 48'

1,49287 (20°)

-

II. Sesquiterpene

265,5 to 266° (750 mm.)

0,9236 (15°)

+ 58° 40'

1,50602 (20°)

Gonystylol5)

137 to 139° (17 mm.)

0,9183 (17°)

+ 40°

-

Mol. refr. found 66,7.

Ledum camphor6) (Ledol)

264°

(752 mm.)

0,9349 (0°)

0,9237 (19°)

-

-

-

Maali alcohol7)

270,8 to 271° (754 mm.)

0,9190 (15°)

[a]D+131,99°

1,52252 (20°)

Mol. refr. found 67,98.

Patchouli alcohol8)

255 to 256°

0,9334 (15°)

- 36° 52'

-

-

1) Schreiner and Kremers, The Sesquiterpenes, Milwaukee 1904, p. 108.

2) Report of Schimmel & Co. October 1904, 24 and April 1910, 46.

3) E. Schmidt, Bed. Berichte 10 (1877), 188.

4) Report of Schimmel & Co. April 1904, 52.

5) Eyken, Recueil des trav. chim. des P.-B. 25 (1906), 44. According to Chem. Zentralbl. 1906, I. 842.

6) Rizza, Journ. russ. phys. chem. Ges. 1887, 319; Berl. Berichte 20 (1887), Ref. 562.

7) Report of Schimmel & Co. November 1908, 139.

8) Report of Schimmel & Co. April 1904, 69.

Sesquiterpenes that have not yet been further characterized have been found in the volatile oil of Blumea balsam i-fera, in the oils of basilicum, cajeput, Abies alba, fennel, hemlock needles, laurel leaves, wild thyme, and milfoil.