The constitution of eriodictyol, of homoeriodictyol and of hesperitin / by Frank Tutin.

  • Tutin, Frank.
Date:
1910
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Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constitution of eriodictyol, of homoeriodictyol and of hesperitin / by Frank Tutin. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    methylated material was examined as above-described, when it readily yielded 2:4: 6-trimethoxyphenyl 3: 4-dimethoxystyryl ketone (m. p. 85° when air-dried; 117-5° when anhydrous), and 2-hydroxy-4: 6-dimethoxyphenyl 3: 4-dimethoxystyryl ketone (m. p. 154°). Monomethylhomoeriodictyol (2 : (j-Dihydroxy-A-methoxyphenyl A-hydroxy-Z~methoxystyryl ketone). — Monomethylhomoeriodictyol, prepared by the action of methyl iodide on the crystalline sodium derivative of homoeriodictyol, was previously described by Power and Tutin (Trans., 1907, 91, 895). A larger amount of this product has now been prepared by heating the above-mentioned sodium derivative with methyl iodide and methyl alcohol. The product thus obtained was dissolved in ether and freed from unchanged homoeriodictyol by extraction with dilute, aqueous sodium carbonate, after which the monomethylhomoeriodictyol was removed by shaking with a concentrated solution of this alkali. The product so obtained crystallised readily from alcohol in hard, yellow, wart- like masses, which melted at 142°. On boiling monomethylhomoeriodictyol for several hours with 30 per cent, aqueous potassium hydroxide, hydrolysis occurred at the double linking, after which vanillin was readily isolated from the reaction mixture. It is evident from this, and considerations previously giveu, that the ONa group in the sodium derivative of homoeriodictyol, which is converted into methoxyl on treatment with methyl iodide, must occupy the 4-position in the phenyl group of the molecule. Monomethylhomoeriodictyol is therefore 2: 6-di- hydroxy-i-methoxyphenyl i-hydroxy-3-methoxystyryl ketone. Hesperitin (2:4: Q-Trihydroxyphenyl 3-Hydroxy-A-methoxystyryl Ketone.) Hesperitin, which is obtained by the hydrolysis of the glucoside, hesperidin, a constituent of the peel of the orange, lemon, and other related fruits, has been stated by Tiemann and Will (Ber., 1881, 14, 970) to be the phloroglucinyl ester of wtoferulic acid. As stated in the introductory portion of this paper, however, the accuracy of this conclusion was doubted by Power and Tutin, and the present author has therefore further investigated the question. Hesperitin, as obtained from Schuchardt, was rccrystalliscd from ethyl acetate, when it melted at 224°, but when mixed with homo- eriodictyol, fusion occurred at 200°. The material so obtained, however, did not agree in its characters with the description of hesperitin as giveu by A. G. Perkin (Trans., 1898, 73, 1037). Thus it formed pale yellow plates, which could not be distinguished