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

  • Tutin, Frank.
Date:
[1910?]
Catalogue details

Licence: In copyright

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

    7/14 page 2058
    The observation of Perkin (loc. cit.) regarding the anomalous character of the sodium derivative of hesperitin has been confirmed, this substance appearing to have the formula Ci6^i306Na,C16H1406. On the other hand, the statement made by Perkin that the product of the action of acetic anhydride on hesperitin is a triacetyl derivative cannot be confirmed, it having been proved that the substance thus formed is tetra-acetylhes'peritin. Experimental. Eriodictyol (2:4: 6-Trihydroxy'phenyl 3: A-Dihydroxystyryl Ketone). A quantity (5 grams) of eriodictyol* was dissolved in alcohol, and an excess of methyl sulphate added, after which a concentrated alcoholic solution of potassium hydroxide was allowed to flow into the hot liquid at such a rate that the mixture was kept gently boiling. The liquid at first showed a tendency to darken, owing to the absorption of oxygen, but this soon ceased as methylation proceeded. Finally, the mixture assumed a dark red colour on the addition of the alkali, which only slowly disappeared. A further quantity of methyl sulphate was added, followed by more alkali, after which the mixture was kept for twenty minutes and then poured into water. The yellow product precipitated by this treat¬ ment was extracted by means of chloroform, the solution being washed, dried, and the solvent removed. The residue thus obtained was boiled with successive portions of dilute, aqueous potassium hydroxide so long as the decanted alkaline liquid was yellow in colour, after which the material insoluble in the alkali was washed and dissolved in alcohol. On inoculating the solution thus obtained with synthetic 2:4: 6-trimethoxyphenyl 3: 4-dimethoxystyryl ketone (see the following paper), crystallisation rapidly ensued. The product so obtained was identical in all respects with the synthetical compound just mentioned. It crystallised in stout, pale yellow prisms, and, when dried in the air, melted at 85°, but in the anhydrous state at 117*5°: 0*1747 f gave 0*4279 C02 and 0*1046 H20. C = 66*8; 11 = 6*4. C^IIwOc requires C = 67*0; 11 = 6*1 per cent. The potassium hydroxide extracts which had been decanted from the crude 2:4: 6-trimethoxyphenyl 3 : 4-dimethoxystyryl ketone were acidified, and the precipitated yellow product was crystallised from alcohol, in which it was rather sparingly soluble. Deep yellow * For an improved method of isolating eriodictyol, homoeriodictyol, and other phenolic substances from Eriodictyon leaves, compare Tutin and Clewer, Trans., 1909, 95, 81, f Anhydrous substance.
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