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U T Oxy Lin. Part III. the Co ‘~1Stit U T Io?A of HGR112 Cx T Oxy Lin

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U T Oxy Lin. Part III. the Co ‘~1Stit U T Io?A of HGR112 Cx T Oxy Lin View Article Online / Journal Homepage / Table of Contents for this issue BRAZILIN AND HBMATOXPLIX. PART 111. 235 H~rnu t oxy lin. Part III. The Co ‘~1stit u t io?a of HGR112 cx t oxy lin . Ey W. H. PERKIN,jun., and J. YATES. HEMATOXYLINis the colouring matter of Hcematoxylon, cccmpechianum, a tree which belongs to the family Ca?suZpiniacece,andthe wood of which appears to have been first imported into Europe by the Spaniards sbortly after the discovery of America. The heart-wood of this trep, known as logwood in this country, is still largely used in cotton and wool dyeing for the production of blacks and greys, and it is also em- ployed on account of its cheapness along with other colours, such as indigo, for dyeing compound shades. The importance of hgmntoxylin may be judged from the fact that it has probably been, and perhaps is still, more largely used than any other natural colouring matter, not even excepting indigo. The dye is sent into the market either as a concentrated liquid extract or in the solid form, the rasped wood, in either case, being extracted with wnter and the extract evaporated in vacuum pans. For dyeing cotton, or in calico printing, logwood extract is generally used in conjunction with an iron, chromium, or aluminium mordant ; the two first-named give intense black, whereas, with the latter, grey- ish-violet shades are produced. Very large quantities of the liquid extract are still used in wool dyeingfor the production of blacks, the wool being immersed alternately in the extract, and in a bath of potass- ium dichromate and sulphuric acid. Again, in silk dyeing, logwood extract is very largely used in conjunction with an iron mordant for the production of blacks, It is worthy of note that hsmatoxglin and Published on 01 January 1902. Downloaded by University of California - Irvine 25/10/2014 07:11:45. iron alum have long been usedas one of the most important stains for microscopical secticns of animal tissues, but, quite recently, Professor S. 5. Hickson (Quart. J. Micros. Xci., 1901, p. 469) has shown that brazilin used with iron alum gives results which are even more sat i s f ct or y . The actual colouring matter of logwood was first isolated by Chevreul (Ann. Chin&.Phys., [ii], 82, 53, 126) in 1810, who obtained it by extracting the wood with water, evaporating the extract to dryness, and digesting the residue with alcohol, which dissolved the hzemxtoxylin, but not the other substauces present. After distilling off the alcohol, the residue was allowed to stand in contact with water, when the haematoxglin separated in crystals, Pure ha?matoxylin is now comparatively easily obtained from the dark coloured crusts which gradually separate when the casks of concentrated logwood extract are allowed to stand in sb cool place. The crude mass View Article Online 236 PERKIN AN11 YA'iES : BRAZILIN AND HACMA'I'OXTLIN. is ground to a fine powder, extracted repeatedly with ether, the ethkr- eal solution evaporated, and the residue left in contact with water when dark coloured crystals separate, which, by recrystallisation from water containing a small quantity of sodium bisulphite, ilzay be obtained colourless, and consist then of pure hzematoxylin. Wsematoxylin crystallises in tetragonal prisms with 3 molecules of water of crjstallisation, and is sparingly soluble in cold, but readily in hot., water ; it dissolves in alkalis, forming an intense purple-coloured solution. It is strongly dextrorotntory, a 1 per cent. aqueous solution having a rotation of 1.85' in a 200 mm. tube; it also reduces Fehling's solution and silver nitrate in the cold. The first attempt to determine the composition of ha3matoxylin is due to Erdmann, who in 1842 (Annalen, 44, 292) proposed the formula C,,H,,O,; this he subsequently altered to C1GHI406, for the au- hydrous substance and this formula, which mas confirmed by Hesse (Amwlen, 1859, 109, 332) and by other workers, is now accepted as correct. From very early times experiments mere made witti the object of obtaining evidence as to the nature of this important dye-stuff, but the results in most cases did not afford any clue t.6 its constitution. The literature bearing on the subject is, in fact, so extended, that it is only possible in this paper to give a very brief outline of such of the work as produced really valuable evidence of the nature of hamatoxylin. Reim (Bey., 1871, 4, 331) showed that when an ethereal solution of hzmatoxylin is mixed with a few drops of nitric acid, oxidation takes place and hzmateh, CI,Hl,O,, is prodtrced. J. J. Hiimmel and A. G. Perkin (Ber., 1882,15, 2337) subsequently obtained hzmate'in pure in the form of reddish-brown crystals by leading air through a solution of the dye-stuff in ammonia. The action of fused caustic potash on haema- Published on 01 January 1902. Downloaded by University of California - Irvine 25/10/2014 07:11:45. toxylin was also first investigated by Reim (Zoc. cit., 332) and from the fused mass he was able to isolate considerable quantities of p.7/i*ogc(.ZZoZ, a result of great importance, since it showed that hzematoxylin is prob- ably a derivative of this substance. R. Meyer (Be?..,1879, 12, 1392) submitted hzematoxylin to dry distillation, and obtained a distillate which he stated contained resorcinol, as well as pyrogallol, but the qualitative tests by which he claimed to have recognised the former of these were quite insufficient, and it will be shown in this paper that resorcinol is not formed in this may. That hsmatoxylin contains several hydroxyl groups was clear from early times, and in order to determine how many such groups were present in the molecule, Reim (loc. cit., 331) investigated its behaviour with acetyl chloride, and obtained a substance which he considered to be hexa-ncetylhzmatoxylin, Cl,H,0,(C2H,0)G, and as a result of this he suggested the first consti- tutiwal formula for hzeinatoxglin, namely, View Article Online PART 111. THE CONSTITUTION OF HBMATOXYLIN. 237 OH OH Erdmann and Schultz (Annulen, 1883,216,234), by determining the number of acetyl groups in this substance, subsequently showed that Reim’s substance was penta-acetyZhcernc~toxyZinand had the formula C1GHB(C2H30)506,and therefore haematoxylin contains only five hydroxyl groups. This result was confirmed by the investigation of the action of sodium methoxide and methyl iodide on hzmatoxylin when, under certain conditions (Herzig, illonutsh., 1894, 15, 143), tetramethylhzematoxylin, Cl,HloO,(OMe),, is produced a substance which still contains a hydroxyl group, since on treatment with acetic anhydride it yields ace tlyltetramethylhaematoxylin, ClGH,0(OMe)4*OC1,H,0. It is thus shown that haematoxylin, like brazilin, contains an alcoholic hydroxyl group which is riot methylated by the action of sodium meth- oxide and methyl iodide, and indeed, from the general similarity between brazilin and haematoxylin, it has long been considered probable that these two colouring matters are closely allied in constitution. During the investigation of brazilin, we have also carried out a niimber of experiments on hematoxylin, the results of which, in our opinion, not only prove the close relationship of these two colouring matters, but also enable us to assign a formula to haematoxylin which we believe correctly represents the constitution of this substance. In the present paper, we describe only the experiments on the oxida- tion of tetramethylhematoxylin with permanganate, and leave for a Published on 01 January 1902. Downloaded by University of California - Irvine 25/10/2014 07:11:45. future communication the description of the interesting substances which have been obtained by oxidising tetramethylhaematoxylin with chromic acid. We have also carefully repeated R. Meyer’s (Zoc. cit.) experiments on the distillation of hzematoxylin, and shorn that pyrognllol (but no re- sorcinol) is produced in considerable quantity in this way. We are thus able to confirm Reims’ discovery (Zoc. cit.) that haematoxylin is probably a derivative of pyrogallol. When tetramethyl hamatoxplin is oxidised with permanganate, it yields m-hemipinic acid, an important result, because it shows that haematoxylin, like brazilin, contains the catechol nucleus. Briefly stated, then, the molecule of brazilin is made up of a resorcinol and a catechol nucleus, whereas haPimatoxylin contains a pyrogallol and a catechol nucleus, From the product of the oxidation of tetramet.hylhzematoxylin, we VOL. LXXXI. R View Article Online 238 PERKIN AND YATES: BRAZILIN AND HBMATOXYLIN. have also been abIe to isolate considerable quantities of a beautifully crystalline acid, CllH1207,which melts at 215O. This acid is dibasic, since it yields a silver salt, CllHloO,Ag, ; it is also converted into the anhydride C,,H,,O, by treatment with acetic anhydride, and as it contains two methoxy-groups and yields pyrogallol when heated in a sealed tube with hydrochloric acid, its constitution is evidently represented by the formula : @Me OM~/\O*CH,*CO,H ()CO,H that is to say, it is 2-carboxg-5: 6-dime~hox~phenoxyaceticacid. This acid is therefore exactly similar to the 2 -carboxy-~-met?~oxyp?~enox?~aceticacid : OMe/\0*CH2*CO,H ()CO,H which was obtained from trimethylbrazilin by oxidation with per- manganate, from which, indeed, it only differs by containing an extra methoxy-group. The close relationship between brazilin and hEma- toxylin which owing to the general similarity in the properties of theso two colouring matters has so long been considered probable, is now clearly proved and may be briefly expressed in the following way. Trimet hy 1brazilin, on oxid a tion, yields 2-car boxy-5-me thoxy phenoxy - acetic acid and m-hemipinic acid, and therefore its constitutional formula must contain the two nuclei : Published on 01 January 1902.
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