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XLYIIL-Robinin, Viozaquercetin, Myrticolorin, and 0Syyitrin

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XLYIIL-Robinin, Viozaquercetin, Myrticolorin, and 0Syyitrin View Article Online / Journal Homepage / Table of Contents for this issue ROBININ, VIOLAQUERCETIN, MPRTICOLORIN, AND OSYRITRIN. 473 XLYIIL-Robinin, VioZaquercetin, Myrticolorin, and 0syyitrin. By ARTHURGEORGE PERKIN, F.R.S.E. Robinin. INa previous communication (Trans., 1900, 77, 430), it was shown that the leaves of Robinia Psezcdacacia contain acacetin, a monomethyl ether of apigenin, an interesting point in view of the discovery by Zwenger and Dronke (Annalen Xuppl., 1861,1,263) that the flowers of the same plant contain a quercetin glucoside, robinin. AS these flowers, however, are practically devoid of dyeing properties, it seemed doubtful whether a quercetin compound was present, and reference to the work of these chemists made ib probable this suspicion was well founded. At the time of Zwenger and Dronke's investigation, the obstinacy with which these colouring matters retain water of crystal- lisation was not fully appreciated, and results accurate in themselves frequently received a wrong interpretation. The analyses of their " quercetin " were made with material dried at looo, a temperature at which it is rarely rendered anhydrous; again, it was unlikely that picric acid mould result from the action of nitric acid on quercetin. Some difficulty wa8 at first experienced in procuring raw material for this investigation, but ultimately this was overcome by the kind- ness of Dr. J. van Rijn, of Maastricht, who was good enough to superintend the gathering and drying of some quantity of the flowers. For isolating robinin, Zwenger and Dronke digested the flowers with boiling water, subsequently evaporating the extract and treating the Published on 01 January 1902. Downloaded by McMaster University 23/10/2014 18:52:43. residue with alcohol. The following method is more rapid, and is suit- able for dealing with small quantities of raw material. The flowers were digested with ten times their weight of boiling alcohol for 4 hours, the mixture strained through calico, and the residue well pressed and again treated in a similar manner. The pale green extract, which deposited a wax on cooling, was concentrated by evaporation, poured into water, and the mixture extracted with ether, the alcohol contained in the aqueous liquid being removed by distilla- tion ; on standing overnight, this solution deposited crystals which were collected and washed with a mixture of alcohol and chloroform until the washings were colourless. The residue was then purified by two or three crystallisations from water with the aid of animal char- coal, One hundred and ninety grams of the flowers gave 1.76 grams, or 0.82 per cent., of robinin in the crude condition, this being reduced approximately one-Ealf on purification. As thus obtained, it consisted of extremely pale yellow needles sinter- VOL. LXXXI. KK View Article Online 474 PERKIN : ROBININ, VTOLAQUERCETIN, ing at 190' and melting at 196-19'7' (2. and D. 195O), and had the general properties mentioned by these authors, When dried at looo i 0.1103 gave 0.3123 GO, and 0.0550 H,O. C = 52-49 ; H= 5.54. C,,H,2020requires C = 52.24 ; H = 5.54 per cent. Zwenger and Dronke assign to robinin at 100' the formula C,,H,oO,G (C = 51.19 ; H = 5.1 l),and with this their analytical figures closely agree. This discrepancy suggested that our preparation might contain a trace of free colouring matter which would raise the percentage com- position. An alcoholic solution of a second preparation was therefore poured into ether (in which the colouring matter is soluble, but not the glucoside) and the precipitated product collected, again crystallised from water, and dried at 100' : 0*1131gave 0.2165 CO, and 0,0575 H20. C=52*20; H=5*64. The glucoside was thus evidently homogeneous. Determinations of the water of cry stallisation contained in the glucoside dried at the ordinary temperature, employing two distinct preparations, gave the following results : 1.6790, at looo, lost 0.2450 H,O. H20=1551. 1'6079, ), ,, 0.2606 H,O. H20=15.58. --- C,3H420,0,8H,0requires H,O = 15-97 per cent, C,3H420,(),7frH20 99 H,O= 15*11 39 Air-dried robinin thus crystallises with 8H,O. These results are not in agreement with those of Zwenger and Dronke, who found 14-53 per cent. of water, agreeing with the amount requiFed for the formula C,,Hao0,,,5~H20, or according to the above, C,3~42020,7H,0.This discrepancy is curious, although the lower figures these authors give Published on 01 January 1902. Downloaded by McMaster University 23/10/2014 18:52:43. for robinin dried at 100' suggest the possibility that their product still contained some water of crystallisation, hCO!rr?,p08itiO9?,with Acid,-The dried glucoside was boiled with dilute sulphuric acid * for at least 2 hours, and after standing overnight, the liberated colouring matter was collected, washed, and dried at 100' : 0.6110, at looo, gave 0.2330 colouring matter. Found, 38.13. 0.9804, ,, ,, 0.3'745 9, ,, 38.11). la2266, ,) ,, 004650 7, ,, 37.92. Zwenger and Dronke, on the other hand, found that air-dried robinin gave 37.96 per cent. of '' quercetin " dried at loo', an amount considerably in excess of that given a.bove. Thus, air-dried robinin, C,,H,20,0,SH,0, should give 33.70 per cent. of the colouring matter C,,H,oO,,H,O, or but 31-70 per cent. of the anhydrous substance. In their paper, they state that robinin is " extremely easily " decom- * 750 C.C.of 1 per cent. solution for each gram of glucoside. View Article Online MPRTfCOLORTN, AND OSYRITRIN. 475 posed by boiling dilute sulphuric or hydrochloric acids, but with acid of 1 per cent. strength this was not found to be the case, for with a short digestion, 39-54 per cent. of “colouring matter ” was obtained, a fact suggesting that it was contaminated with unaltered glucoside. The CoZouring Mattey.- For analysis, the product was recrystallised from dilute alcohol and dried at 160’ : 0.1122 gave 0.2589 CO, and 0-0355 H,O. C= 62.93 ; H = 3.51. C,,H,,O, requires C = 62.93 ; H = 3.49 per cent. Zmenger and Dronke found that this colouring matter, dried at loo’, gave C=59*31, H=4.49, numbers in close agreement with those required for the formula C:,,H,,O,,H,O (C = 59.2, H = 3’94). Prepared as above, it crystallised in slender, yellow needles melting at 276-278’, readily soluble in boiling alcohol, and soluble in alkaline solutions with a pale yellow colour, For additional proof that it was not quercetin, comparative dyeing trials were carried out employing woollen cloth mordanted with chromium, aluminium, tin, and iron. Chromium. Aluminium, Tin. Iron. Quercetin .....,....,...,... Red-brown. Brown-orange- Bright Olive-black. yellow. orange. Robinin colouring matter Brownbyellow. Full golden- Lemon-yellow. Deep olive- yellow. brown. With mineral acids in the presence of acetic acid, it yielded crystal- line compounds, and to confirm its molecular weight the sulphuric acid derivative was analysed. 0&1556gave 0.2657 CO, and 0.0457 H20, C = 46.57 ; H = 3.26. Cl,H,,06,H,S0, requires C = 46-87 ; H = 3.12 per cent. Published on 01 January 1902. Downloaded by McMaster University 23/10/2014 18:52:43. Alcoholic potassium acetate yielded a monopotassium salt, but owing to lack of material this was not fully investigated. The acetyl derivative, prepared in the ueual manner, crystalliaed from methyl alcohol in colourless needles : 0.1093 gave 0,2438 CO, and 0*0400H20. C = 60.83 ; H = 4a06. C,,H,O,(C,H,O), requires c = 60.79 ; H = 3.96.per cent. When fused with alkali, the colouring matter gave p-hgdroxybenxoic acid (m. p. 208-210°) and phloroglucinol. These facts, together with a comparative dyeing trial, conclusively proved that the colouring matter derived from robinin is identical with that isolated from the flowers of the Delphinum ConsoZida (Proc., 1900, IS, 182). This similarity was corroborated by the peculiar behaviour of their acetyl derivatives when heated ;thus, while some preparations melted at 180--182O, others became liquid at about 116O, resolidified as the temperature rose, and finally melted at 180-182’. The colour- KK2 View Article Online 476 PERKIN : ROBININ, VIOLAQUERCETIN, ing matter is in reality hmpherol, first obtained by aordin (Diss. Berne) by the decomposition of its monomethyl ether karnpheride, which is contained in galanga root (AZpinia oficinarum). This, as Kostan- ecki suggests (Ber., 1901, 34, 3723), has in all probability the con- stitution and may be considered as the connecting link between apigenin and yuercetin. Kampherol, and not guercetin, is the colouring matter pro- duced when robinin is hydrolysed with acid. The Sugars.-The acid filtrates formed by the decomposition of robinin were neutralised with barium carbonate, filtered, and evaporated to a small bulk. The product yielded an osazone which after three crystallisations from dilute alcohol was obtained as a spongy mass of yellow needles sintering at 165' and melting at 178-180°. As a further treatment in this manner did not yield a homogeneous substance, it was dissolved in alcohol, the solution poured into ether, and well washed with water. On slow evaporation, a small quantity of crystalline matter separated, and this was collected, washed with ether, and recrystallised from alcohol. It melted at 204-205O and resembled glucosaxone. The filtrate which contained the main bulk of the osazone, on spontaneous evaporation, deposited crystals which were extracted with benzene, washed with traces of ether, and recrystallised from dilute alcohol, In the preliminary notice (Proc., 1901, 17, 87), it was Published on 01 January 1902. Downloaded by McMaster University 23/10/2014 18:52:43.
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