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

  • Power, Frederick B. (Frederick Belding), 1853-1927
Date:
1914.]
Catalogue details

Licence: Public Domain Mark

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

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    a dihydroxycoumarin, such as daphnetin or gesculetin, since the latter compounds, which melt at 253—256° and about 270° respec¬ tively, are known to give a yellow colour with alkalis and a green coloration with ferric chloride. An analysis ol the substance, and a determination of the molecular weight by the microscopic method, gave the following results: 0-0842* crave 0*2000 CO, and 0'0323 IDO. 0 = 64*8; 11 = 4-3. 0'0424 * in 5 c.c. of alcohol, using benzil as the standard, was between 0 045 and 0047 mol. Mean M.W. = 183. Umbelliferone, C9IIG03, requires 0 = 66*7; 11 = 3*7 i>er cent. M.W. = 162. Dihydroxycoumarin, C9HG04, requires C = 60*7; 11 = 3*4 per cent. M.W. = 178. The remainder of the substance was acetylated, and the product crystallised from water in three fractions, which possessed the following characters: (1) M. p. 137°. Mean M.W. (in acetone solution by the micro¬ scopic method) =207. The melting point (140°) of a known specimen of acetyluinbelli- fcrone (M.W. = 204) was not depressed by admixture with this fraction, and the substances were apparently identical. (2) M. p. 130—133°. An analysis of this fraction gave 0 = 63*8; H = 4*3. Acetylumbelliferone, CnH804, requires 0 = 64*7; 11 = 3*9 per ceut. Diacetyldihydroxycoumarin, C]3H10OG, requires C = 59*5; 11 = 3*8 per cent. (3) M. p. 115—118°. The mean molecular weight of this frac¬ tion, in acetone solution, was 228. C13H10O6 requires M.W. =262. These results served to confirm the conclusion that the above- described substance, melting at 237—239°, consisted chiefly of umbelliferone, together with a small proportion of a dihydroxy¬ coumarin. Isolation of Umbelliferone Methyl Ether. The ethereal extract of the aqueous liquid, which had been extracted with aqueous sodium carbonate, as above described, was subsequently shaken with aqueous potassium hydroxide, which re¬ moved a small amount of a crystalline substance. On finally wash¬ ing and drying the ethereal liquid, and evaporating the solvent, a much larger amount of the same substance was obtained. This material was recrystallised from dilute alcohol, when it separated in flat needles of a slightly yellowish colour, melting at 115—116°.