The constituents of the flowers of Anthemis nobilis / by Frederick Belding Power and Henry Browning, Jun.

  • Frederick Belding Power
Date:
1914.]
Catalogue details

Licence: Public Domain Mark

Credit: The constituents of the flowers of Anthemis nobilis / by Frederick Belding Power and Henry Browning, Jun. Source: Wellcome Collection.

    6/18 page 1834
    was a glucoside of apigenin (1:3 : d'-trihydroxyfiavone), C15H10O5, but that, in addition to water of crystallisation, it contained a molecule of water which could not be eliminated without decom¬ position. The formula of the glucoside is therefore to be repre¬ sented as C21H20O10,H2O. A compound obtained by Yongerichten (Annalen, 1901, 318, 124; 1902, 321, 71) by the partial hydrolysis of apiin, and desig¬ nated as <Aglucoseapigenin, was stated to melt at 215—220°, and, when dried at 120—130°, to possess the formula C21H20O10. When crystallised from dilute alcohol it contained an amount of water agreeing approximately with 2 molecules. Inasmuch as the apigenin glucoside obtained from chamomile flowers differed in some respects from the compound described by Vongerichten (loc. cit.), especially in its melting point and the elements of an addi¬ tional molecule of water, it was deemed desirable to prepare some of the latter compound for the purpose of comparison. The product obtained by the partial hydrolysis of a commercial speci¬ men of apiin, in exact accordance with the method given by Vongerichten (loc. cit.), was found to melt at 192—195°, the higher melting point (215—220°) recorded by the last-mentioned investigator having probably been due to the presence of a little apigenin produced by further hydrolysis, which was also indicated by the results of his analysis of ^-glucoseapigenin. It would appear that the latter compound undergoes partial hydrolysis on simply boiling its aqueous solutions, and in this respect also it differs from the glucoside obtained from chamomile flowers, which remains quite unchanged by this treatment. The product from apiin, melting at 192—195°, was analysed with the following result: 0*1084, on heating at 110—120°, lost 00092 H20. H20 = 8'5. 0-0992 * gave 0-2120 C02 and 0‘0440 H20. 0 = 58-3; H = 4‘9. C21H20O10 requires C = 583; H = 4*6 per cent. C'21H20O10,2H2O requires H20 = 7‘5 „ „ With consideration of these results, the apigenin-d-glucoside obtained from chamomile flowers is to be regarded as a new compound. Hexa-acetylapigenin-d-glucoside, C21Il14O10(CO*CIl3)6.—A portion of the glucoside was heated for some time with acetic anhydride containing a small proportion of pyridine. The product of the reaction, after removing the greater part of the acetic anhydride, was poured into water, and the deposited substance collected. This substance, when separated from a mixture of alcohol and ethyl acetate, was obtained in colourless, microscopic crystals, melting * Dried at 110—120°.
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