Oil From The Wood. From the sawdust of the southern cypress, Taxodium distichum, Rich, growing in the swamps of Virginia, A. P. Odell3) obtained with 95 p. c. alcohol an extract which, upon distillation under diminished pressure (35 mm.) yielded a fraction boiling between 180 and 190° and another between 217 to 222°. From the first fraction a substance with the following properties was isolated: b. p. 182 to 185° (35 mm.); d20o/4o 0,9469; aD dextrogyrate; nD20o 1,5040. As to elementary composition, it corresponded with the formula C12 H20 O. The molecular refraction (found 56,29, computed 53,16) indicated the presence of two double bonds the presence of which was verified by the addition of four atoms of bromine. This new substance, named cypral by the author, is regarded as an aliphatic aldehyde, since it yields the characteristic reactions with silver nitrate and fuchsin sulphurous acid.
1) The Cypresse des Montezuma, which occurs in the cemetery of Santa Maria del Tule near Oaxaca. It has a height of 40 m. and the circumference of its trunk is said to measure 30 m. De Candolle estimated the age of this tree at 6000 years, von Humboldt at 4000 years.
2) Report of Schimmel & Co. April 1909, 98.
3) journ. Americ. chem. Soc. 33 (1911), 755.
The higher boiling portions of the alcoholic extract contained a hitherto unknown sesquiterpene which Odell named cypressene, and which was characterized by the following constants: b. p. 218 to 220° (35 mm.), 295 to 300° (778 mm.); d18/4 0,9647; [a]D20o+6,53°; nD22o 1,5240. The molecular refraction was found to be 64,66, indicating one double bond (computed 62,55). In accordance therewith the sesquiterpene added 2 atoms of bromine. With moderately concentrated nitric acid cypressene yielded a yellow, amorphous oxidation product, with concentrated sulphuric acid a decidedly red color.
Oil From The Comes. The same investigator1) has likewise prepared and examined the oil from the cones. Cones distilled in September yielded one percent, of a greenish-yellow oil that had the odor of pinene. Cones collected later in the year yielded 1,5 to 2 p. c. of oil that was darker in color and more decidedly lemon-like as to odor, d 0,86 and 0,850; aD + 18,0 and +35,5°; alcohol content 2,5 p. c. The oil contained about 85 p. c. of d-a-pinene (b. p. 156 to 157°; d18o/4o0,8616; [a]D + 30,8°; nD20o 1,4655; m.p. of nitrosochloride 103°), and 5 p. c. of d-limonene (m". p. 175 to 180°; d18/4oo 0,9567; [a]D20o + 98,3°; nD20o1,4748; m.p. of tetrabromide 104°, of nitrosochloride 105°), also 2 p. c. of a fraction which probably contained a pseudoterpene alcohol as indicated by the flocculent precipitate produced upon the addition of Beckmann's reagent. In addition the distillate contained 3 p. c. of carvone (d18/4oo 0,960; nD20o1,500; m.p. of semicarbazone 162 to 163°), also 3 p. c. of a dextrogyrate, tricyclic sesquiterpene probably identical with the cypressene of the wood oil, which had the following properties: d18/4o 0,9335; nD20o1,5039.
1) Journ. Americ. chem. Soc. M (1912), 824.