(Turcz., in Bull. Mosc, 1849, ii, 23, Syn. E. leptophylla, Miq.)

A Mallee.

Systematic. - A tall shrub, with several thin stems, branched from near the base, with a smooth, red, or ashy-grey bark, coming off in thick flakes, branches erect. Leaves narrow-lanceolate, about 3 inches long, under 1/2 inch wide, light green in colour, somewhat shining, generally terminated by a short, narrow, hooked apex, from which the specific name is, in this instance, derived, conspicuously black-dotted, especially underneath. Peduncles mostly in the axils of the leaves, each bearing an umbel of about six to eight small flowers; operculum obtusely conical or acuminate, occasionally of a reddish colour.

Fruit. - Small, globular, or pear-shaped, more or less shining; rim comparatively broad, sometimes countersunk; valves thin, acuminate, tips just exserted; 2 to 3 lines long and up to 2 lines in diameter.

E. odorata and E. Behriani more closely match these than any other.

Habitat. - Far interior of New South Wales; Western Australia; South Australia; Victoria.

ESSENTIAL OIL. - Leaves and terminal branchlets for distillation were forwarded by Mr. Walter Gill, the Conservator of Forests, South Australia. The material was collected at the Parilla Forest Reserve, of that State, in November, 1919. The yield of oil was 1.4 per cent. The crude oil was of an orange-brown colour, and had an odour indicating those of the "Mallee" oils, allied to the "Box" group. Aromadendral was quite pronounced. The constituents present besides the aromadendral were dextro-rotatory pinene, cymene, cineol, the sesquiterpene, and alcoholic bodies. Phellandrene was absent.

The crude oil had specific gravity at 15 °C. = 0.9111; rotation aD - 2.4°; refractive index at 200 = 1.4754, and was soluble in 5 volumes 70 per cent. alcohol. The saponification number for the esters and free acid was 13.5; after acetylation, it was 54.5, thus indicating 11.6 per cent. of free alcohols having a C10Hl8O molecule.

On rectification, 1 per cent. distilled below 1600 C. (corr.). Between 160-172°, 10 per cent. distilled; between 172-192°, 71 per cent. came over, and between 192-260°, 18 per cent. distilled. These fractions gave the following results: -

I he cineol, determined by the resorcinol method in the portion distilling below 192°, and calculated for the original oil, was 40 per cent. By the rapid phosphoric acid method it was 20 per cent., showing the presence of a considerable amount of constituents, other than cineol, absorbed by the resorcinol.

400 c.c. of the crude oil were distilled, and the portion which came over below 188° C. (corr.) separated; this equalled 66 per cent. This portion had specific gravity at 15° = 0.8976; rotation aD + 1.2°; refractive index, 1.4706. The saponification number for the esters and free acid was 9-2. After acetylation this was 29, indicating 5.6 per cent. of alcoholic bodies with the C10H18O molecule. The aldehydic absorption was 5 per cent.

The cineol in this large portion, determined by the resorcinol method, was 45 per cent., and by the phosphoric acid method 35 per cent. This result indicates that bodies other than cineol were absorbed by the resorcinol. No less than 11 per cent. distilled between 188-192°, which portion was evidently largely absorbed.

The aromadendral was separated by acid sodium sulphite from the portion boiling above 188°; when purified it had optical rotation aD - 49.8°.

The cymene was determined in the portion distilling below 1880 C. The cineol was removed by phosphoric acid, and 50 per cent. resorcinol. The remaining oil was distilled, and the required fraction separated. This had specific gravity at 15° C. = 0.8642; rotation, nil, and refractive index at 20° = 1.4845. A portion was oxidised by potassium permanganate in the usual way. The finally prepared acid melted at 155-156° C, thus indicating p-oxyisopropyl-benzoic acid, the oxidation product of p-cymene.