The constituents of olive leaves / by Frederick B. Power and Frank Tutin.

  • Frederick Belding Power
Date:
[1908?]
Catalogue details

Licence: In copyright

Credit: The constituents of olive leaves / by Frederick B. Power and Frank Tutin. Source: Wellcome Collection.

    10/18 page 898
    It was then allowed to cool, when the acetyl derivative separated in colourless, glistening leaflets : 0-0994 gave 0-2749 C02 and 0-0881 H20. C = 75-4 ■ H = 9*8. C31H4803(C0*CH3)2 requires 0 = 75-8 ; H = 9-7 per cent. Diacetyloleanol is very readily soluble in chloroform, only moderately so in ethyl acetate, and nearly insoluble in cold alcohol. It is recrys¬ tallised most conveniently from acetic anhydride. When diacetyloleanol is heated, fusion takes place at about 208°, the exact temperature depending on the rate of heating, gas is then evolved, and the liquid quickly re-solidifies. The solid so obtained is insoluble in alcohol, and only sparingly soluble in ethyl acetate or acetic anhydride, and is not acted on by the latter. It is very readily soluble in chloroform or benzene, but crystallises from a mixture of one part of the latter and two parts of petroleum (b. p. 90—120°) in small tufts of colourless needles, which do not melt at a temperature of 310°. This substance is unaffected by alkalis, and, when dissolved in chloroform, slowly decolorises a solution of bromine in the same solvent. On analysis, it yielded the following results : 0-1128 gave 0-3280 C02 and 0-1063 H20. C = 79 3; H = 10*5. 0-1049 „ 0-3058 C02 „ 0-0990 H20. C = 79-5 ; H = 10-5. Cc ,3iH4S03 requires C = 79'4; H = 10*3 per cent. This result indicates that, on heating diacetyloleanol, both the acetyl groups are removed, but, as no water is present during the operation, they are not eliminated by hydrolysis. The change might be repre¬ sented as follows : -C-O-CO-CHj -C*0*CO*CIL -C*0 I I -c*o I + ch3*co*co*ch3. This view is in harmony with the fact that the high melting product contains no hydroxyl group, and the loss of weight suffered by the original acetyl derivative on being heated is also in agreement with it: 0*1648 of diacetyloleanol, on heating at 230°, lost 0-0254 CH„*CO. CH3*CO = 15'4. 031H4803(CO*CH3)2 requires 0112*00 = 15 5 per cent. Mbnoacetyloleanol, C31H4S02(0H)*C0*CII3.—A quantity of diacetyl¬ oleanol was dissolved in 85 per cent, alcohol, and the solution boiled for forty-five minutes. On cooling the liquid, a product was obtained which crystallised in needles melting at 258°. This substance was much more soluble in alcohol than diacetyloleanol, and was evidently a monoacetyloleanol, since it readily yielded the diacetyl derivative on treatment with acetic anhydride. After drying at 110°, it was analysed :
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