The constitution of eriodictyol, of homoeriodictyol and of hesperitin / by Frank Tutin.
- Tutin, Frank.
- Date:
- 1910
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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![leaflets were thus obtained, which melted at 154°, and were identical with the 2-liydroxy-4: 6-dimethoxyphenyl 3: 4-dimethoxystyryl ketone described in the following paper: 0 1279 gave 0 3099 CO., and 0 0680 H20. C = 661; H = 59. C19H20Ob requires 66'3; H = 5’8 per cent. M onomethyleriodictyol (2: G-Dihydro.ryA-m ethoxy phenyl 3: 4 -di- hydroxystyryl ketone).—Four grams of eriodictyol were dissolved in absolute alcohol, and to this solution was added one and a-half molecular proportions of methyl sulphate, which had just previously been washed with aqueous sodium carbonate and dried. Slightly more than the equivalent amount of sodium, dissolved in absolute alcohol, was then gradually introduced into the hot mixture. After removing the alcohol, the residue was dissolved in ether, washed with water, and then fractionally extracted by shaking with suc- cessive portions of an aqueous solution of sodium carbonate. The first few extractions removed only unchanged eriodictyol, which formed the greater part of the product, but on acidifying the alkaline liquids subsequently obtained, a yellow product separated, which partly crystallised on keeping. This was collected, well washed with alcohol, and then recrystallised from this solvent, in which it was but sparingly soluble. Almost colourless needles were thus obtained, which melted at 216°: 0'1284 gave 0'2995 C02 and 0'0583 H20. C = G3'6; H = 5‘0. C]6H1406 requires C = 63'5; II = 4 6 per cent. This substance was therefore a monomethyleriodictyol, and since it is not identical with either homoeriodictyol (2:4: 6-trihydroxy- plienyl 4-hydroxy-3-methoxystyryl ketone) or hesperitin (2:4: 6-tri hydroxyphenyl 3-hydroxy-4-methoxystyryl ketone), and the hydroxyl group in the 2(or 6)-position is known to be difficult of methylation, it must be 2: 6-dihydroxyA-metlioxyphenyl 3: A-dihydroxyslyryl ketone. Monomethyleriodictyol dissolves in aqueous alkali hydroxides, giving at first a practically colourless solution, but after about thirty seconds the liquid suddenly becomes totally black. On acetylation, monomethyleriodictyol yields a tetra-acetyl derivative, which forms colourless needles, melting at 159°. Ilomoeriodictyol (2:4: 6-Trihydroxy phenyl i-Uydroxy-3-mcthoxy- styryl Ketone). The methylation of homoeriodictyol by means of methyl sulphate and potassium hydroxide proceeded analogously to that of eriodictyol, with the exception that there was no tendency to absorb oxygen, and consequently a cleaner product was obtained. The](https://iiif.wellcomecollection.org/image/b22433156_0010.jp2/full/800%2C/0/default.jpg)
