This section is from the book "A Research On The Eucalypts Especially In Regard To Their Essential Oils", by Richard T. Baker, Henry G. Smith. Also available from Amazon: A Research On The Eucalypts And Their Essential Oils.
(J.H.M., Proc. Linn. Soc, N.S.W., 1904, p. 475.)
Systematic. - A tree of medium height, with a peppermint baric. Abnormal leaves narrow, ovate lanceolate, petiolate, alternate, thin, margin slightly crenu-late, usually under 3 inches long. Branchlets angular. Normal leaves broad lanceolate, oblique to falcate, acuminate, up to 10 inches in length, older leaves rather thick and shining; venation not prominent, except in young leaves, intramarginal vein distart from the edge, lateral veins spreading, oblique. Peduncles axillary or lateral, 3 to 6 lines long with umbels of six to twelve flowers. Buds clavate; calyx tube narrow, conoidal, tapering to a slender pedicel; operculum hemisphere al, sometimes shortly pointed.
Fruit. - Pyriform or inclined to conical, shortly pedicellate, only slightly contracted at the orifice; rim broad, flat or slightly domed, shining, reddish in colour; valves scarcely exserted; 5 lines long and 3 1/2 lines in diameter.
These might easily be mistaken for E. campanulata, which they somewhat resemble. The next in similarity are E. virgata and E. Sieberiana.
Habitat. - Coastal and Coast Range districts of New South Wales; and Gippsland, Victoria.

REMARKS. - Only in herbarium material is it possible to confound it with the species mentioned under the fruits. The field characters, however, especially the bark (peppermint), are sufficient to distinguish it from those.
ESSENTIAL OIL. - Leaves and terminal branchlets for distillation were obtained from Nowra, N.S.W., in March, 1912. The yield of oil was 1.2 per cent. The crude oil was light amber in colour, and had an odour similar to that given by the cineol-phellandrene Eucalyptus oils generally, with a secondary one somewhat aromatic. The oil was fairly rich in cineol; contained some phel-landrene, although this was small in amount at this time of the year; pinene was present and rather a large proportion of what appears to be the liquid form of eudesmol. This is shown by the constants for the third fraction, and also by those obtained with the higher fractions of the portion boiling above 1900 C, in the first distillation. It is doubtful if piperitone was present, if so, the amount was very small. A small quantity of a solid paraffin was detected, and terpineol was also present.
The crude oil had specific gravity at 150 C. = 0.9207; rotation aD + 2.9°; refractive index at 200 = 1.4737, and was soluble in 2 volumes 70 per cent, alcohol. The saponification number for the esters and free acid was 3.7.
On rectification 1 per cent, distilled below 173° C. (corr.). The odour of valeraldehyde was pronounced in this portion. Between 173-1940, 67 per cent, distilled; between 194-245,° 8 per cent, came over, and between 245-2780, 19 per cent, distilled. These fractions gave the following results: -
First traction, sp. gr. at 15 C . | = | 0.9070; rotation aD - 0.3o ; refractive index at 200 = 1.4636. | |||
Second | " | " | " | = | 0.9154; rotation aD + 0.3°; refractive index at 200 = 1.4707. |
Third | " | " | " | = | 0.9396; rotation aD + 12.4°; refractive index at 200 = 1.5000. |
The cineol was determined by the resorcinol method in the first fraction; when calculated for the crude oil the result was 51 per cent. By the phosphoric acid method it was 40 per cent, when calculated for the crude oil.
The first fraction had a yellowish tint, due to the influence of the phenols, and was rich in cineol. The saponification number was only 2.3, so that low-boiling esters were practically absent.
A portion of the oil boiling above 1900 was acetylated, the saponification number for this was 74.6. This high number was due to the eudesmol, which was present in the liquid form.
Determinaiion of the higher boiling portion. - 100 cc. of the oil boiling above 1900 C. were again distilled. 3 per cent, came over below 1830 C. Between 183-208°, 19 per cent, distilled; between 220-2650, 19 per cent, came over, and between 265-2900, 50 per cent, distilled. These fractions gave the following results: -
first fraction, sp. gr. at 15 C. | = | 0.9179; rotation aD + 1.4o , retractive index at 200 = 1.4684. | |||
Second | " | " | " | = | 0.9337; rotation aD + 3.6°; refractive index at 200 = 1.4874. |
Third | " | " | " | = | 0.9523; rotation aD + 18°; refractive index at 200 = 1.4983. |
The first fraction contained a good quantity of cineol. It is possible that terpineol was present in the second fraction, as the indications were for that alcohol. The third fraction consisted largely of the liquid form of eudesmol and the sesquiterpene.
Both the second and third fractions were acetylated with the following results: -
Second fraction, saponification number before | = | 4.8; | after | = | 96.8. | ||||
Third | " | " | " | " | = | 2.8; | after | = | 91.8. |
This result indicates that about 35 per cent. of eudesmol was present in the third fraction.
One hundred cubic, centimetres of the crude oil were distilled under reduced pressure, and the lower boiling portion removed. The oil distilling between 138-148° C. under 7 millimetres pressure was again distilled and separated into two fractions; one distilling between 130-134° C, under 7 millimetres, the other between 140-146° C. under 5 millimetres pressure. The two fractions gave the following results: -
First fraction, sp. gr. at 15o C | = | 0.9040: rotation aD + 8.6o; retractive index at 200 = 1.5023. | |||
Second | " | " | " | = | 0.9697; rotation aD + 15.4°; refractive index at 200 = 1.5058 |
A portion of the second fraction was boiled with water under a reflex for four days, but the crystalline form of eudesmol was not obtained. A portion seeded with eudesmol" had not crystallised after fourteen days, although the crystals had apparently grown. The identity of this alcohol is thus not so com pletely shown as was the case with the oil of E. Rossii, for instance, which was changed into the crystalline form on distillation under reduced pressure. (See under that species, and also the article dealing with eudesmol.)
 
Continue to: