(F.v.M. & MlQ., Ned. Kr. Arch., IV, 140.) Cabbage or Weeping Gum.

Systematic. - A tree reaching 40 or 50 feet in height, with spreading limbs, weeping branches, and branchlets that hang down 10 or 12 feet, the latter often glaucous or reddish. Abnormal leaves alternate, petiolate, ovate to ovate lanceolate, up to 8 inches long and 3 inches broad; venation prominent, almost parallel to the mid-rib. Normal leaves lanceolate to linear lanceolate, thick, shining, acuminate, often falcate, about 5 inches long; venation almost parallel to the mid-rib. Oil glands numerous. Umbels of about six to twelve flowers, borne on axillary or lateral peduncles about 4 lines long. Buds glaucous, somewhat clavate, about 4 lines long. Calyx tube tapering to base ; operculum hemispherical, usually shortly pointed.

Fruits. - Broadly turbinate, truncate; rim red, broad, horizontal or slightly domed; valves not exserted; 4 lines long and 5 lines broad.

The main features which distinguish these fruits from E. coriacea- its nearest affinity, are their larger size and more woody nature.

Habitat. - New South Wales, Victoria, Tasmania.

REMARKS.-This tree was described by Miquel in 1856 (Ned. Kruidk. Arch.," iv, 140), on behalf of Baron Mueller, from the Tasmanian specimens of Stuart. Bentham, in bis "Flora Australiensis " (vol. iii, p. 210), synonymises it with E. coriacea, A Cunningham, under which species Mueller also places it in his " Eucalypto-graphia " (1879). Possibly Mueller had not seen specimens of Cunningham's E. coriacea when he described this species in conjunction with Miquel, and so probably was not acquainted with the New South Wales and mainland trees now going under the name of E. coriacea, that is, Cunningham's and Sieber's tree-E. pauciflora of the latter- and so considered he had a new species at the time, for we know that later he placed it under E. coriacea. Since that date it has been customary to regard the Tasmanian and mainland trees as one species, but the investigations taken in connection with our research work show that such is not the case, and that the two are separate species, and so Mueller was correct after all. The original name of E. phlebophylla is thus restored. Mueller, however, concurs in Bentham's synonym (supra) in his ' Eucalyptographia " and places the Tasmanian and mainland trees under E. coriacea in that book. This lumping of species, even his own, was characteristic of the Baron in his later work. Maiden, in his "Critical Revision of Eucalypts," agrees with Bentham's and Mueller's later classification. The differences between this species and E. coriacea, with which it has been associated by various botanists, are fully detailed in our publication on the Tasmanian Eucalypts, Roy. Soc. Tas., 1912, p. 27-9. Maiden disagrees with our classification, Roy. Soc. Tas., 1914, p. 27, but the botanical and chemical results favour separation

ESSENTIAL OIL. - Material for distillation was collected at Ttmbridge, Tasmania, in June, 1912. The yield of oil was 1 per cent. The crude oil was light olive-brown in colour, had a terpene-like odour, and consisted principally of lævo-rotatory pinene; cineol and eudesmol were both present, the latter in quantity, as it crystallised from the higher boiling fraction. The so-called "Cabbage or Weeping Gum" is common both in Australia and Tasmania. Oil was first distilled from this Eucalypt by Mr. Marsden, at Muloon, near Boro, N.S.W., in February, 1908, and it was brought under our notice by Mr. Farrell, of the Australian Eucalyptus Oil Company, on account of its strong odour of turpentine, and the low temperature at which it boiled. When submitted to us it was a colourless oil, as it had been rectified, and was found to contain a small amount of cineol, and to consist almost entirely of kevo-rotatory pinene, with some eudesmol. In September, 1910, Mr. Farrell noted this species growing at Monga, N.S.W., and he had the leaves distilled, and submitted the crude oil to us for investigation. The oil was light olive-brown in colour, had an odour of turpentine, was very mobile, and besides consisting largely of lævo-rotatory pinene, contained some cineol and eudesmol. Even more pinene was present than in the Tasmanian oil, but this may be due to the difference in the time of the year, or partly to the mode of distillation, as the Monga oil had been distilled from an ordinary pot-tank still, which naturally does not bring over the high boiling constituents so completely as when the steam is supplied from a boiler. The Monga oil had specific gravity at 15o C. = 0.8766; rotation aD - 32.5°; refractive index at 20o = 1.4679; and contained 11 per cent. of cineol by the resorcinol method. Over 80 per cent. of the total oil distilled below 170o C. (corr.).

The oil from the Tasmanian trees (our own distilling) had specific gravity at 15o C. = 0.8925; rotation aD - 22.4°; refractive index at 20o = 1.4752, and was insoluble in 10 volumes 80 per cent. alcohol. The saponification number for the esters and free acid was 3.2.

On rectification, a very small amount of acid water and volatile aldehydes came over below 157o C. (corr.). Between 157.172o 66 per cent. distilled; and between 172-192o, 9 per cent.; the temperature then quickly rose to 2650, only a few drops distilling; and between 265-2820, 20 per cent. distilled, which largely consisted of crystallised eudesmol and the sesquiterpene. These fractions gave the following results: -

The cineo was determined by the resorcinol method in the portion distilling below 192° C, and when calculated for the original oil represented 9 per cent.; the absorption, however, might include some eudesmol brought over in the distillate. The pinene was determined in the first fraction, and an amount equal to 30 per cent, of the total oil came over between 156-157o C. It had an odour resembling ordinary turpentine. The specific gravity at 150 C. = 0.8661; rotation aD - 38.1°; and refractive index at 20o = 1.4650. The nitrosochloride was easily prepared with it, and this melted at the correct temperature. It may be assumed, therefore, that 50 or 60 per cent. of the oil of this Eucalyptus consists of laevo-rotatory pinene, and this is confirmed by both the Monga and Muloon samples. Whilst the chief constituent of the oil of this species is pinene, that of the oil of E. coriucea is phellandrene. Other differences are also shown between the oils of these two species.

In August, 1919, Mr. A. R. Penfold distilled oil from the leaves of this species growing in the Braidwood District, N.S.W. The oil agreed in constituents and characters with those recorded above, and consisted practically of lævo-rotatory pinene and crystallised eudesmol. Phellandrene was absent and cineol only present in traces. The yield of oil was 1.45 per cent. The crude oil had specific gravity at 15o C. = 0.9132; rotation aD -19.1°, refractive index at 200 = 1.4836°. The saponification number for the esters and free acid was 4. A portion of the oil was acetylated in the usual way. The saponification number was then 101.8, while in the cold with two hours' contact it was 20.8. The high saponification number was largely due to the eudesmol.

On rectification the oil commenced to distil at 154° C. Between 154.169°, 35 per cent, distilled; between 169 and 190°, 17 per cent. came over; between 190-268°, 7 per cent. distilled; and between 268-290°, 38 per cent. distilled. 100 c.c. of the oil was then steam-distilled, and 60 per cent. collected. The remainder in the flask soon crystallised into a solid mass, and pure eudesmol was prepared from this.

On rectifying the first distillate no less than 50 of the 60 per cent, distilled between 155-157°, principally at 156° C. This had specific gravity at 15° = 0.8625 ; at 20° = 0.8588. Specific rotation [a]D - 50.18°, and is thus one of the highest lævo-rotatory pinenes known. The pure eudesmol had specific rotation [a]D + 27.07°, and melted at 79-80° C.