The constituents of the leaves of prunus serotina / by Frederick B. Power and Charles W. Moore.

  • Frederick Belding Power
Date:
[1910?]
Catalogue details

Licence: In copyright

Credit: The constituents of the leaves of prunus serotina / by Frederick B. Power and Charles W. Moore. Source: Wellcome Collection.

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    alcohol. If to its solution in acetic anhydride a few drops of concentrated sulphuric acid are added, a fine pink colour is pro¬ duced, which slowly passes through violet to blue, finally becoming green. Two of the oxygen atoms contained in prunol are, as shown below, present in the form of hydroxyl groups, one of which possesses phenolic properties, whilst the other is evidently alcoholic, as only a mono-sodium derivative could be obtained. The state of combination of the third oxygen atom is not known, but it was ascertained by means of Perkin's modification of the Zeisel method that no methoxyl or ethoxyl group was present. Diacetylprunol, C31H4803(C0*CH3)2.—This was obtained by heat¬ ing prunol with acetic anhydride. The resulting liquid, when concentrated and kept for some time, slowly deposited the diacetyl derivative in handsome, glistening needles, which melted at 181°: 0*1442 gave 0*3995 C02 and 0*1255 H20. C = 75*6; H = 9*7. C35H5405 requires C = 75’8; 11 = 9*7 per cent. A determination of its specific rotatory power gave the following result: 0*1814, made up to 20 c.c. with chloroform, gave aD +1°8/ in a 2-dcm. tube, whence [a]D + 62*4°. Diacetylprunol is readily soluble in ether, chloroform, and ethyl acetate, and also in hot alcohol, but is only moderately soluble in cold alcohol. As already stated, it melts at 181°, but if the tem¬ perature is raised to about 220°, acetic anhydride is evolved and the mass solidifies, after which it only melts above 300°. The substance so obtained is insoluble in boiling alcohol, but dissolves readily in benzene. If to its solution in boiling benzene hot alcohol is added, the substance is obtained in small, glistening, colourless plates, which melt at about 315°: 0*1546 gave 0*4434 CO, and 0*1404 H20. C = 78*2; H = 10*l. C66Hio20: requires C = 78*7; H = 10*l per cent. This result indicates that on heating diacetylprunol two molecules of the compound lose one molecule of acetic anhydride, the residual complexes becoming united by an oxygen atom, as follows: CHQ-CO„-CQ1H,J> ‘3 vv2 ) •CO ‘Co, H 1QCr 2(CH3*C0,0)2*C31H480 = (CH3*C0)20 + br,3 ^31^48' A somewhat similar change takes place on heating diacetyl- oleanol (loc. cit., p. 898), but in this case both the acetyl groups are eliminated from one molecule of the compound. Monoacetylprunol, C31II4802(0H)*C0*CH3.—If diacetylprunol is dissolved in hot 70 per cent, alcohol, and the solution boiled for about two hours, one acetyl group is removed, and, on cooling the
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