Terpineol was also prepared from the second and third hour oils of this species, distilled from material growing at Nerrigundah, New South Wales. 500 c.c. boiling above 190° C. were repeatedly fractionated at 10 millimetres pressure, the following fractions being eventually obtained (temperatures uncorrected): -

The fraction 99-101° C. at 10 millimetres had: -

When shaken with 5 per cent, sulphuric acid a good yield of terpin hydrate was eventually obtained.

The fractions 101-1040 and 105-1090 gave results agreeing with those of the first sample, and geraniol was readily detected in the higher-boiling fraction.

The terpineol from the Nerrigundah oil was thus in agreement with that from the Youri material, although showing a slightly less lævo-rotation. There was, however, a difference of four years in the dates of distillation of the two samples. This species is probably the best of all the Eucalypts from which to distil an oil containing the maximum amount of terpineol.

(b) Terpineol From The Oil Of E. Phellandra

The "second hour" oil of this species was distilled for us by Messrs. Gillard Gordon, Ltd., at Braidwood, New South Wales, in November, 1919. It had the following characters: - Specific gravity at 150 C. = 0.9035; rotation aD - 1575°; refractive index at 20° C. = 1.4708; soluble in 1 1/2 volumes 70 per cent. alcohol, and contained a considerable amount of phellandrene. The cineol, determined by the resorcinol method in the portion distilling below 190° C. was 52 per cent. when calculated for the crude oil. By the phosphoric acid method the result was 30 per cent. The saponification number for the esters was 10.3; after acetylation it was 57 by heating and 25.3 in the cold with two hours' contact.

4,000 c.c. were distilled, when 80 per cent. came over below 190° C. This fraction, and the portion boiling above that temperature, gave the following results: -

By repeated fractionation of the portion boiling above 190° at 10 millimetres, 67 c.c. were obtained boiling at 100-1010 C. (uncorr.). This had the following characters: -

When shaken with 5 per cent. sulphuric acid a good yield of terpin hydrate was eventually obtained.

The terpineol in the oil of E. phellandra is thus shown to have a higher lævo-rotation than has that in the oil of E. Australiana.

(c) Terpineol From The Oil Of E. Carnea

The oil of E. carnea had a high saponification number, and an attempt was made to determine the alcohol of the ester. The oil was saponified in the ordinary way, afterwards rectified, and the fraction boiling below 190° C. removed. The higher boiling portion was repeatedly rectified under reduced pressure, when a fraction distilling at 100-1030 C. at 10 millimetres was eventually obtained. This had the following characters: -

When repeatedly shaken with 5 per cent. sulphuric acid, terpin hydrate was formed in some quantity. The terpineol in the oil of this species was thus shown to have a considerable dextro-rotation. The ester was chiefly terpinyl-acetate.

(d) Terpineol From The Oil Of E. Diversicolor

The saponification number for the original oil of this species was even higher than for that of E. carnea.

When rectified, 32 per cent. remained, boiling above 190° C. This portion had saponification number 1297 by heating, and 34 in the cold with two hours' contact. It was then saponified in the usual way and 'the volatile acids separated and determined, the result being 86.9 per cent. barium-acetate and 13.1 per cent. barium-butyrate. The saponified oil was subjected to repeated distillation under reduced pressure until a fraction was obtained boiling at 99-100° C. at 10 millimetres. This had: - -

It eventually gave a good yield of terpin hydrate when repeatedly shaken with 5 per cent. sulphuric acid.

The terpineol in the oil of this species was apparently combined with both acetic and butyric acids, but chiefly with the former. It may be assumed, therefore, that terpinyl-acetate is a constant constituent in the oils of the earlier members of the genus, and that the alcohol is highly dextro-rotatory. In the oils of the more recent groups the predominant terpineol appears to be mostly lævo-rotatory.