518 Transactions. 



Art. LVI. — Studies on the Chemistry of the Neiv Zealand Flwa. 

 By T. H. Easterfield and J. C. McDowell, B.Sc. 



lEead^before the Wellington Philosophical Society, [27th [October, 1915.] 



PART v.— THE CHEMISTRY OF PODOGARPUS TOTARA AND PODOCARPUS 



SPICATUS. 



(1.) PODOCARPUS TOTARA. 



In Part iv of this series (Trans. N.Z. Inst., vol. 43, 1911, p. 55) it was 

 mentioned that a crystalline substance can be extracted by alcohol from 

 totara sawdust. 



In a preliminary experiment 150 grams of dry totara sawdust were 

 boiled for two hours and a half with 90 per cent, alcohol, and yielded 

 18 grams of vacuum-dry resinous extract. About 70 per cent, of the 

 extract was soluble in ether, yielding a light-coloured solution. The residue 

 obtained by evaporating the ethereal solution was amorphous, but yielded 

 beautiful crystals when its solution in light petroleum was allowed to evapo- 

 rate spontaneously. Thirty kilograms of totara sawdust were then percolated 

 with alcohol, and the extract treated in the same way as in the preliminary 

 experiment, but, owing to the difficulty of treating such a large quantity 

 without special appliances, a smaller percentage yield of dry extract was 

 obtained. 



The residue left, on evaporating the light petroleum extract of the resin 

 prepared by alcohol can be distilled in a partial vacuum without decom- 

 position, and this is the quickest method of purifying the material. The 

 distillate is a light-yellow liquid, which solidifies to a transparent glass if 

 quickly cooled. The glass may be kept for months without showing any 

 sign of crystallization, but, if it be moistened with light petroleum, crystals 

 rapidly begin to form. 



The name " totarol " is proposed for this crystalline substance, since, as 

 will be shown, it is a tertiary alcohol. 



Pure totarol melts at 127° C. (corrected) ; in a 4-per-ceiit. alcoholic 

 solution the specific rotation [A]d = 42-08° ; in an 8-per-cent. solution the 

 value is 42-18°. It is insoluble in water and aqueous alkali, intensely 

 soluble in alcohol and ether ; 100 grams of light petroleum (b.p. 50°-80°) 

 dissolve 18 grams of totarol at 15° C. A very small quantity of alcohol 

 prevents the substance from crystallizing from light petroleum. 



An alcoholic solution of totarol is neutral to phenol-phthalein, and does 

 not react with alcoholic potash, hydrochloric acid, or ferric chloride. 



The chemical formula for totarol is C20H30O, as shown by the following 

 analyses and molecular- weight determinations : — 



I. 0-1057 grams yielded 0-3248 gm. COg and 0-0997 gm. HgO. 

 II. 0-1003 „ 0-3076 „ 0-0949 „ 



III. 0-1162 „ 0-3569 „ 0-1099 „ 



Calculated for 



C =83-9 



H = 10-49 . . 



