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.
(R.T.B., Proc. Linn. Soc, N.S.W., 1906, p. 303).
Systematic - A tall tree, attaining a height of 100 feet, with a dark-coloured, stringy bark, persistent to the branchlets. Abnormal leaves opposite, sessile, cordate, ovate, acuminate, thin, pale-coloured on the under side, shining, up to 6 inches long and 3 inches broad. Normal leaves lanceolate falcate, up to 9 inches long and from 1 to nearly 3 inches wide, often very oblique at the base especially the larger leaves, coriaceous, pale-coloured on both sides; venation less pronounced than in abnormal leaves, intramarginal vein well removed from the edge, lateral veins distinct, oblique and spreading. Inflorescence usually in terminal panicles, but sometimes in axillary umbels. Calyx tube turbinate, gradually tapering into the flattened pedicel; operculum hemispherical, shortly acuminate.
Fruit. -Hemispherical; rim thin ; valves sunken ; about 3 lines in diameter.
The fruits morphologically much resemble those of E. acmenioides.
Habitat.-Richmond River, and North Coast district, New South Wales.

REMARKS. - This species is placed as a variety of E. acmenioidti by J. H. Maiden, "Critical Revision," vol. i, p. 263, but as no new data are advanced to justify its reduction to varietal rank, the reasons given when originally described (loc. cit.) as a species still hold, and so we can only regard it as a true species.
ESSENTIAL OIL. - Leaves and terminal branchlets for distillation were obtained from Lismore, N.S.W., in August, 1900. The yield of oil was 0.16 per cent. The crude oil was of a light orange-brown colour, and had a not unpleasant odour. It consisted largely of pinene, which was dextro-rotatory, and phel-landrene was quite absent. Cineol was present, but only about 5 to 10 per cent. A very pronounced constituent occurring in this oil was the ester terpinyl-acetate. Only a small quantity of free acetic acid was present in the crude oil, but the ester was partly decomposed on distilling the oil under atmospheric pressure.
The crude oil had specific gravity at 150 C. = 0.8963 ; rotation aD + 37.2° ; refractive index at 20° = 1.4681, and was soluble in 7 volumes 80 per cent. alcohol. The saponification number for the esters and free acid was 35.8.
On rectification 2 per cent. came over below 1620 C. (corr.). Between 162-1720, 53 per cent. distilled; between 172-1930, 27 per cent. distilled, and between 193-270°, 16 per cent. came over. These fractions gave the following results: -
First fraction, sp. gr. at 150 C. | = | 0.8715; | rotation aD | + | 33.3°. | |||
Second | ,, | ,, | ,, | = | 0.8954; | ,, | + | 35.5°. |
Third | ,, | ,, | ,, | = | 0.9121; | ,, | not taken. | |
A second consignment of material for distillation was received a month later from Lismore, N.S.W., in order that the comparative constancy of the constituents in the oils might be tested. The two samples were practically identical, as is shown by the following table :-
Locality and date. | Specific gravity at 150 C. | Optical rotation aD | Saponification number. | Yield of oil per cent. |
Lismore, 2nd August, 1900............................... | 0.8963 | + 37.2° | 35.8 | 0.155 |
Lismore, 5th September, 1900 ........................... | 0.8901 | + 39.0° | 35.29 | 0.169 |
In January, 1902, the ester content was again determined in the crude oil of the first sample in order to see what alteration, if any, had taken place during that period. The free acid had increased slightly in amount, otherwise the ester was constant. In the cold with two hours contact with alcoholic potash, no further alteration was shown, so that it is evident that geranyl-acetate hardly occurs in the oil of this species.
The Lismore, September, sample (supra), was stored in the dark, and in December, 1919, was again analysed. Very little alteration had taken place during the nineteen years the oil had been kept. On distillation 78 per cent. came over below 190° C. The crude oil and the rectified portion gave the following results: -
Crude oil, sp. gr. at 150 C. | = | 0.8981; rotation aD + 36.8°; refractive index at 200 = 1.4681. |
Rectified portion ,, | = | 0.8790; rotation aD + 34.4°; refractive index at 20° = 1.4647. |
The cineol was determined by the resorcinol method in the rectified portion; when calculated for the crude oil the result was 11 per cent.
The acetic Acid ester. -The amount of ester occurring in the oil of this species is somewhat large, and as the redistillation had demonstrated the presence of acetic acid, which had been derived from the decomposition of an ester, it was decided to proceed further, particularly as the amount of the free acid present in the crude oil was quite small. A quantity of the crude oil was boiled for some time with aqueous potash under a condenser, the aqueous portion separated, evaporated down and tillered. It was then acidified with sulphuric acid, and the volatile acids distilled over until all had been obtained. Qualitative tests showed that acetic acid was present in quantity, but the odour of valeric acid had also been detected, so that it is most probable that both acids were present. (See also the article on the Valeric Acid Ester in Eucalyptus Oils.)
The distillate was exactly neutralised with barium hydrate solution, and the mixed barium salt purified and prepared in the usual manner. The amount of barium was then determined as barium sulphate ; 0.4858 gram. of the barium salt on ignition gave 89.3 per cent. of BaS04, so that the amount of barium acetate in the mixed salt was 90.85 per cent., and the barium valeriate 9.15 per cent., assuming that valeric acid was the only other acid present besides acetic. This result suggests that valeric acid may be present as an ester in many crude Eucalyptus oils, and to be connected with the valeraldehyde which occurs so frequently in certain groups. Acetic acid is the free acid occurring in Eucalyptus oils, which is demonstrated in the article dealing with this subject, and it is also present in the oil of E. Macarthuri, E. acervula, and other numerous species as an ester in combination with geraniol. The alcohol of the ester occurring in the oil of E. camea has now been determined, and that it is not geraniol is shown by the ester not saponifying in the cold when treated with alcoholic potash ; it was proved to be dextro-rotatory terpineol. The portion boiling above 1900 C. was saponified and the separated oil distilled under reduced pressure. A portion was eventually obtained boiling at 99-1030 C. at 10 millimetres. This had specific gravity 0.93; rotation aD + 60°; refractive index at 200 = 1.484, and gave a fair yield of phenylurethane melting at no° C. This is further evidence that terpineol was formed early in the genus, similarly with geraniol, and probably continues throughout the oils of the entire group.
 
Continue to: