Quercitron Bark.Glucosides of Quercetin.Rutin.(CHAPTER VII. Flavonol Group.)

The Natural Organic Colouring Matters
By
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds
and
Arthur Ernest Everest, D.Sc., Ph.D., F.I.C., of the Wilton Research Laboratories; Late head of the Department of Coal-tar Colour Chemistry; Technical College, Huddersfield
Longmans, Green and Co.
39 Paternoster Row, London
Fourth Avenue & 30th Street, New York
Bombay, Calcutta, and Madras
1918

Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.

Rutin was discovered by Weiss (Chem. Zentr., 1842, 305) in the leaves of a rue (Ruta graveolens, Linn.), and was subsequently isolated from capers (Capparis spinosa, Linn.) by Rochleder and Hlasiwetz (Ann. Chem. Pharm., 82, 196), and by Schunck (Manchester Memoirs, 1858, 2 Ser., 155, 122) from buckwheat (Fagopyrum esculentum, Moench.). Whereas Hlasiwetz (Ann. Chem. Pharm., 96, 123) came to the conclusion that rutin was identical with quercitrin, it was shown by Zwenger and Dronke (ibid, 123, 145) that this could not be the case, because on hydrolysis rutin gives quercetin and two molecules of sugar. Schunck (Chem. Soc. Trans., 1888, 53, 262; 67, 30) considered that the formula of rutin is C₂₇H₃₂O₁₆, 2H₂O, and that on hydrolysis it is converted into quercetin and 2 molecules of rhamnose, C₂₇H₃₂O₁₆+3H₂O=C₁₅H₁₀O₇+2C₆H₁₄O₆. Rutin, moreover, was identical with the sophorin, which Foerster (Ber., 15, 214) had isolated from the Sophora japonica.

It has been shown by Schmidt (Chem. Zentr., 1901, ii., 121) that by the hydrolysis of rutin glucose is also produced, the formula of this substance being therefore C₂₇H₃₀O₁₆.C₂₇H₃₀O₁₆ + 3H₂O = C₁₅H₁₀O₇ + C₆H₁₂O₆ + C₆H₁₄O₆

Rutin forms pale yellow glistening needles, sparingly soluble in water, and is said to melt above 190°. With alcoholic potassium acetate it gives a bright yellow monopotassium salt (Perkin, Chem. Soc. Trans., 1899, 75, 440).

According to Schmidt, violaquercitrin (violarutin) is identical with rutin (ibid.) 1908, 246, 274), and Perkin (ibid., 1910, 97, 1776) has shown that osyritin (Colpoon compressum, Berg.) (Osyris compressa) (ibid., 1902, 81, 477) and myrticolorin {Eucalyptus macrorhyncha, F. Muell.) (Smith, ibid., 1898, 73, 697) in reality consist of this substance (loc. cit.).

The dyeing properties of rutin are similar to, though weaker than those of quercitron bark. The following shades are given on mordanted woollen cloth:
Chromium. Brown-yellow.
Aluminium. Full golden-yellow.
Tin. Lemon-yellow.
Iron. Dull brown.