The constituents of olive leaves / by Frederick B. Power and Frank Tutin.
- Frederick Belding Power
- Date:
- [1908?]
Licence: In copyright
Credit: The constituents of olive leaves / by Frederick B. Power and Frank Tutin. Source: Wellcome Collection.
9/18 page 897
![were obtained, and also some portions of amorphous material which could not be caused to crystallise from any solvent. It was at first thought that these amorphous products might contain a second sub¬ stance, but on acetylation they gave an almost quantitative yield of the diacetyl derivative of the crystalline substance, with only a little amorphous matter. As first obtained, the crystalline substance melted at about 301°, but on recrystallisation the melting point was raised to 303—304°, wThen it remained constant, no decomposition occurring. After drying at 110°, it was analysed : 0*1127 gave 0-3271 C02 and 0-1088 H20. C = 79T ; H = 10*7. 0-1135 „ 0-3291 C02 „ 0-1083 H20. C = 791 ; H = 10*6. C3iH50O3 requires C = 79*1 ; H = 10-6 per cent. No substance of the formula C31Hri0O3 has previously been described, and it is therefore proposed to designate the new compound oleanol. Oleanol is not very soluble in any of the usual organic solvents, but is moderately so in boiling chloroform, from which it separates in an amorphous condition. When crystallised from ordinary alcohol, it contains one molecule of water of crystallisation, as shown by the following analysis : 0*3466 of air-dried substance, on heating at 110°, lost 0-0130 H20. H20 = 3-7 0-1136 of air-dried substance gave 0-3152 C02 and 0'1107 H>0. C = 75-7; H = 10-8. C31H50O8,H2O requires H>0 = 3-7 ; C = 76*2 ; H = 10’7 per cent. Two of the oxygen atoms contained in oleanol are, as shown below, present in the form of hydroxyl groups, and one of the latter possesses phenolic properties. In consequence of this fact, the substance reacts with sodium carbonate and hydroxide, giving an insoluble, amorphous sodium derivative. The third oxygen atom present in oleanol probably occurs in an ether linking, since the compound does not react with hydroxylamine. It was ascertained, however, by means of Perkin’s modification of Zeisel’s method, that no methoxyl or ethoxyl group was present. When oleanol is gently warmed with concentrated sulphuric acid, a deep orange colour is produced, and, when dissolved in chloroform, it does not decolorise a solution of bromine in the same solvent. A determination of the specific rotatory power of oleanol gave the following result: 0-3032, dissolved in 25 c.c. of chloroform at 30°, gave aD -I-1°54' in a 2-dcm. tube, whence [a]D 4- 78-3°. Diacetyloleanol, C31 H4803(C0*CH3)2.—A quantity of oleanol was dissolved in acetic anhydride, and the solution boiled for some time.](https://iiif.wellcomecollection.org/image/b30613152_0009.jp2/full/800%2C/0/default.jpg)
