Cuminic aldehyde1) (m. p. of semicarbazone 201 to 202°; m. p. of cuminic acid 114 to 116°).
\-LinalooIl) (oxidation to citral; m. p. of citryl-?-naphthocin-choninic acid 197°).
l) Report of Schimmel & Co. April 1902, 14. - H. Walbaum and O. Huthig, Journ. f. prakt. Chem. II. 66 (1902), 47.
2) Report of Schimmel & Co. October 1892, 47.
Linalyl isobutyrate1) is probably present. Fraction 80 to 111° (6 to 7 mm.), after having been treated with bisulphite, yielded a saponification number of 20,4. Upon saponification it yielded, in addition to a pungent acid (possibly formic acid), one with a distinct odor of St. John's bread. However, the silver determination of the silver salt did not agree with the silver content computed for silver isobutyrate. This discrepancy may be attributable to admixed silver formate or silver acetate.
Eugenol1) (m. p. of benzoate 69 to 70°).
The Seychelles cinnamon oil has a composition similar to that of the Ceylon cinnamon oil. It differs merely by the presence of camphor. An oil with the following properties was examined by Schimmel & Co.-), d15o0,9670; aD - 4°44'; aldehyde content 32 p. c. The following substances were found: cinnamic alder hyde (m. p. of semicarbazone 211°), eugenol (m. p. of benzoate 69 to 70°), l-B-phellandrene (m. p. of nitrite 103°), cymene (m.p. of p-hydroxyisopropyl benzoic acid 156 to 157°; of propenyl benzoic acid 255 to 260°), and camphor (m.p. of oxime 116 to 118°).
In the first fractions of a Seychelles cinnamon oil Schimmel & Co.3) also found the following substances: Small amounts of a hydrocarbon that boiled below 155° the nitrosochloride of which was decomposed instantaneously at 86 to 87°, camphene (m.p. of /soborneol 209 to 210°), B-pinene (m. p. of nopinic acid 125 to 126°), traces of \-limonene (m. p. of nitrosochloride 103 to 104°; of nitrolpiperidide 93°), benzaldehyde (m.p. of semicar-bazone 212 to 214°), linalool (m. p. of phenylurethane 59 to 62°), and mere traces of a higher aldehyde that had the odor of nonylic aldehyde.
Adulteration and Examination. Ceylon cinnamon oil is very frequently adulterated with the cheaper cinnamon leaf oil. From Ceylon, apparently, no pure bark oils enter the market, for all the oils from this source were found, upon examination, to contain leaf oil. Naturally, it cannot be decided whether the leaf oil has been added to the finished bark oil, or, what is perhaps more probable, whether the leaves have been distilled together with the chips.
1) Footnote 1, p. 420.
2) Report of Schimmel & Co. October 1008, 41.
3) Ibidem April 1918.
Inasmuch as the admixture of leaf oil increases the eugenol content appreciably, thereby decreasing the cinnamic aldehyde content in like proportion, the detection of such sophistication is not difficult. All that is necessary is to make an approximate quantitative determination of both substances.
After the determination of the specific gravity, which is increased by the addition of appreciable amounts of leaf oil, the cinnamic aldehyde content is determined in the well known manner. If this amounts to less than 65 or more than 76 p. c. the oil is suspicious. If less than 65 p. c. are found the amount of eugenol in the oil deprived of its cinnamic aldehyde is determined. For this purpose one of several methods may be followed. The best results are obtained by the rather complicated method of Thorns, according to which the eugenol is weighed as benzoyl eugenol (see Vol. I, p. 596). It suffices, however, to determine the phenol content by shaking with three percent, caustic alkali as directed in Vol. I, p. 590. In a pure oil the eugenol content does not, as a rule, exceed 10 p. c. If more be found, this generally is indicative of adulteration with leaf oil.
To what extent the adulteration with leaf oil is carried on becomes apparent from the reports by Umney1) and by Schimmel & Co.-). The results of the examination of seven oils that were imported directly from Ceylon and bought in London are dealt with. All of these oils were heavily adulterated with leaf oil: three samples contained at least 30 p.c. of leaf oil and four not less than 50 p.c.
The four last mentioned oils had the following properties: -
Cinnamic aldehyde content
Eugenol content (according to Thorns)
1) Pharmaceutical Journ. III. 25 (1895), 949. 2) Report of Schimmel & Co. October 1895, 65.
Ceylon cinnamon oils that have been adulterated with cassia oil have a higher specific gravity, and, as a rule, a higher cinnamic aldehyde content. Oils with more than 76 p. c. aldehyde are suspicious. At least they are inferior, for cinnamic aldehyde is not the constituent that imparts to the cinnamon oil its value as it does to cassia oil. In the case of cinnamon oil, the non-aldehydic constituents are of greater value, a circumstance that is readily demonstrated by the fact that several times the price of cassia oil is paid for cinnamon oil though the latter contains less aldehyde1).
Statistics. The amount of cinnamon oil exported from Ceylon is comparatively small. Considerable, however, is the amount of waste bark which, in the form of chips, is annually exported for the purpose of distillation.
The following quantities of chips were exported: -
1896 . . .
808502 lbs. 1904 . . .
1897 . . .
1905 . . .
1898 . . .
1906 . . .
1899 . . .
1907 . . .
1900 . . .
1908 . . .
1901 . . .
1909 . . .
1902 . . .
1910 . . .
1903 . . .
1911 . . .
By way of comparison, the amounts of quills exported during the last two years may be mentioned: in 1910, 3283202 lbs., in 1911, 3128542 lbs.
The price of chips averages 40 to 45 shillings per hundred-weight (= 112 lbs. = 50,8 kg.), whereas that of the quills is higher, 4 to 5 times as great.