tag:blogger.com,1999:blog-25901510792608948962024-03-13T12:05:44.959+02:00ColoriastoColoriasto on väriaiheisten tekstien (ja kuvien) verkkoarkisto<br>
(Archive for colour themed articles and images)
INDEX: <a href="https://www.coloriasto.net">coloriasto.net</a>Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.comBlogger5502125tag:blogger.com,1999:blog-2590151079260894896.post-8981847282126867442023-12-29T22:00:00.001+02:002023-12-29T22:00:10.981+02:00Delphinium consolida, Flowers (Kaempferol)(CHAPTER VII. Flavonol Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p><em>Delphinium consolida</em> is a common European plant belonging to the Larkspur family; its name refers to its powers, real or imaginary, of healing or consolidating wounds. The blue flowers were examined by Perkin and Wilkinson (Chem. Soc. Trans., 1902, 81, 585) to determine if these yield the same colouring matters as those previously isolated from the flowers of the <em>D. zalil</em> (<em>ibid.</em>, 1898, 73, 267). The presence of kaempferol only could, however, be detected. For its isolation an aqueous extract of the flowers was digested at the boiling-point with addition of sulphuric acid, and the brown resinous product which separated on keeping, extracted with alcohol and the extract evaporated to a small bulk. Addition of ether to this solution caused the precipitation of resinous impurity, and on evaporating the ethereal liquid a semi-crystalline residue of the crude colouring matter was obtained. The product was crystallised from dilute alcohol, converted into acetyl derivative, and this after purification retransformed into colouring matter in the usual manner. The yield was approximately 1 per cent.</p>
<p>[---]</p>
<p>Kaempferol possesses well-defined dyeing properties, and gives with mordanted woollen cloth the following shades which closely resemble those given by morin (<em>loc. cit.</em>):<br />
Chromium. Brownish-yellow. <br />
Aluminium. Yellow. <br />
Tin. Lemon-yellow. <br />
Iron. Deep olive-brown.</p>
<p>It is also present in the <em>Impatiens balsamina</em> (Chantili Pass), the <em>Erythrina stricta</em> (vernacular name "Kon kathet"), (Perkin and Shulman, Chem. Soc. Proc., 1914, 30, 177), the berries of the <em>Rhamnus catharticus</em> (<em>loc. cit.</em>), and together with quercetin, both apparently as glucosides, in the flowers of the <em>Prunus spinosa</em> (Perkin and Phipps, Chem. Soc. Trans., 1904, 85, 56). For the separation of the two colouring matters a fractional crystallisation from acetic acid was employed, kaempferol in these circumstances being the more sparingly soluble.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-87969096890497427972023-12-28T19:25:00.002+02:002023-12-28T19:25:52.760+02:00Galanga Root(CHAPTER VII. Flavonol Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Galanga root is the rhizome of <em>Alpinia officinarum</em> (Hance) and is a native of China. It is employed in the form of a decoction as a remedy for dyspepsia.</p>
<p>Galanga root was first examined by Brandes (Arch. Pharm., (2), 19, 52), who isolated from it a substance which he named kaempferide, but this, according to Jahns (Ber., 1881, 14, 2385), was a mixture of three substances, kaempferide, alpinin, and galangin. The subject was later examined by Gordin (Dissert., Berne, 1897), and by Ciamician and Silber (Ber., 1899, 32, 861) and Testoni (Gazzetta, 1900, 30, ii., 327), and it is now clearly demonstrated that galanga root contains kaempferide, galangin, and galangin monomethylether. According to Testoni, the alpinin of Jahns is a mixture of galangin and kaempferide.</p>
<p><em>Kaempferide</em>, C<sub>16</sub>H<sub>12</sub>O<sub>6</sub>, consists of yellow needles, melting-point 227-229°, soluble in alkaline solutions with a yellow colour. Sulphuric acid gives a blue fluorescent yellow solution.</p>
<p>[---]</p>
<p><em>Galangin</em>, C<sub>15</sub>H<sub>10</sub>O<sub>5</sub>, the second constituent of galanga root, crystallises in yellowish-white needles, melting-point 214-215°, soluble in alkaline solutions with a yellow colour. With acetic anhydride, it gives a <em>triacetyl</em> derivative, C<sub>15</sub>H<sub>7</sub>O<sub>5</sub>(C<sub>2</sub>H<sub>3</sub>O)<sub>3</sub>, melting-point 140-142° (Jahns), and by means of methyl iodide a <em>dimethylether</em>, C<sub>15</sub>H<sub>8</sub>O<sub>3</sub>(OCH<sub>3</sub>)<sub>2</sub>, melting-point 142°.</p>
<p>[---]</p>
<p>[---] Galangin dyes with mordanted woollen cloth the following shades:<br />
Chromium. Olive-yellow.<br />
Aluminium. Yellow. <br />
Tin. Lemon-yellow. <br />
Iron. Deep olive.</p>
<p>[---]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-19691766099835799722023-12-27T19:48:00.004+02:002023-12-27T19:48:38.606+02:00CHAPTER VII. Flavonol Group.Introduction, Flavonol <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>It is usual to subdivide the great family of yellow colours derived from flavone into two classes, <em>flavone</em> and <em>flavonol</em>, and the latter group is distinguished by the fact that the hydrogen in the γ-pyrone ring of these compounds is substituted by hydroxyl, whereas in the former it is not.</p>
<p>Flavonol) so designated by v. Kostanecki, was synthesised by v. Kostanecki and Szabranski (Ber., 1904, 37, 2819) in the following manner:</p>
<p>By the action of amyl nitrite and hydrochloric acid in alcoholic solution on flavanone, isonitrosoflavanone, melting-point 158-159°, is produced, and this by means of boiling dilute acids splits off hydroxylamine and is converted into flavonol.</p>
<p>Flavonol crystallises from alcohol in yellow needles, melting-point 167-170°. When warmed with aqueous sodium hydroxide it forms a yellow liquid, and on cooling the sodium salt separates in the form of yellow needles. Its solution in sulphuric acid exhibits an intense violet fluorescence. Acetylflavonol, colourless needles, melts at 110-111°.</p>
<p>According to Auwers and Müller (Ber., 1908, 41, 4233) benzylidenecoumaranones can be converted into flavonols. Thus benzylidene 4 methylcoumaranone dibromide when treated with potassium hydroxide gives 2 methylflavonol. The reaction may be thus expressed : [KUVA PUUTTUU]</p>
<p>The hydrolysis of flavonol into 0-hydroxybenzoylcarbinol and benzoic acid may be expressed by the following equations [KUVA PUUTTUU] and this reaction, which is typical of the behaviour in these circumstances of the whole series of these compounds, has in general been employed to ascertain their structure. It is best effected by digesting the fully methylated flavonols with boiling alcoholic potash for some hours, for owing to the occurrence of secondary reactions it cannot be satisfactorily carried out with the unmethylated compounds.</p>
<p>For the synthesis of numerous flavonols, many of which occur naturally, v. Kostanecki and his co-workers have employed as a general method that found serviceable for the preparation of flavonol itself, and many instances of this are given in the sequel. The flavonols, with the exception of morin, which curiously enough is colourless, are yellow crystalline substances, soluble in alkaline solutions with a yellow colour, and yield with ease in the presence of acetic acid orange crystalline oxonium salts. According to Perkin, whereas as a rule hydroxyflavones are not oxidised by air in alkaline solution and can be precipitated therefrom unchanged by acids, flavonols on the other hand are readily decomposed in this manner with the formation of water-soluble products.</p>
<p>Interesting is the fact that though certain colouring matters of this group do not possess two hydroxyls in the ortho-position relatively to one another, they are nevertheless strong dyestuffs, and of these the tetrahydroxyflavonol morin may be taken as an example [KUVA PUUTTUU]</p>
<p>That this peculiarity arises from the presence of the pyrone hydroxyl is evident if the structure of morin is compared with the lotoflavone of Dunstan and Henry (<em>loc. cit.</em>) the tinctorial properties of which are exceedingly feeble. It seemed possible that this dyeing effect was to be attributed to the fact that this compound contains the hydroxyl (i) in the peri-position to the chromophore and which is present in most of the natural dyes of this group. Such a suggestion, however, became untenable on the synthesis of resomorin by Bonifazi, v. Kostanecki, and Tambor (Ber., 1906, 39, 86), which dyes the same shades as morin but does not contain the peri-hydroxyl in question. Evidently therefore the tinctorial properties of these hydroxy flavonols can only be accounted for by their possession of the grouping [KUVA PUUTTUU] the effect of which is considerably strengthened by the presence of hydroxyls in other positions in the molecule, and this has received support from the observation of v. Kostanecki and Szabranski that flavonol itself dyes on aluminium mordant a pale yellow shade. Though ortho-hydroxyl groups are not essential to the dyeing property of hydroxyflavonols, their presence, at least in certain positions, has considerable influence, not only in deepening the tone, but also in reddening the shade. Thus, whereas morin dyes bright yellow shades, quercetin gives a brown-orange shade on aluminium mordant, and the effect of the pyrone hydroxyl is very evident on comparing quercetin with luteolin which gives in the same way only a bright yellow colour. A multiplication of hydroxyls does not effect any general alteration of shade given by these compounds, as is so well known to take place in the anthraquinone group, and this affords support to the theory of Watson previously mentioned.</p>
<p>The shades given by the flavonols are not so fast to light as those given by the flavone luteolin, and this may arise in part owing to the greater susceptibility of their salts (or lakes) to oxidation. In this respect they vary again among themselves, quercetin being a somewhat faster colour than fisetin, and morin than quercetin.</p>
<p>On the other hand, the character of the shade given by the natural dyestuff varies in tone, as to whether the colouring matter is present as glucoside or in the free condition. Thus in dyeing with quercitron bark, quercitrin and not quercetin is the dyestuff, whereas in old fustic no glucoside is present, and the tinctorial effect is due to morin itself. The shade again given by a glucoside is naturally dependent on the position of the sugar nucleus, and thus the quercetin glucoside, quercimeritrin (see Cotton Flowers) has quite distinct properties in this respect from quercitrin itself. Again, a glucoside may be almost devoid of tinctorial property, as in the case of the kaempferol glucoside robinin and the alizarin glucoside ruberythric acid. The idea formerly held that glucosides in general were not true dyestuffs, and that during the dyeing operation by the action of the mordant they were hydrolysed with production of the colour lake of the free colouring matter, is incorrect. This evidently arose from the fact that in certain of these dyestuffs, as, for instance, madder and Persian berries, the glucoside is accompanied by its specific enzyme, which in case the temperature of the dye-bath is gradually raised from the cold upwards, effects the hydrolysis of the glucoside before the dyeing operation has really commenced.</p>
<p>In the following pages the natural dyestuffs containing flavonols, or their glucosides, are as far as possible arranged as to the number of hydroxyls present in the colouring matter, commencing with those which contain least. As, however, in many plants more than one flavonol is present, it has obviously not been possible to adhere strictly to this method of classification.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-69094101679237684472023-11-15T19:26:00.004+02:002023-11-15T19:29:25.499+02:00Butea frondosa(CHAPTER VI. The Chalkone and Flavanone Groups.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>The <em>Butea frondosa</em>, also called <em>Dhak</em> or <em>Pulas</em>, is a fine tree, 30-40 feet high, belonging to the order <em>Leguminosæ</em>. It is common throughout India and Burma, and is found in the North-West Himalaya, as far as the Jhelum River. The flowers, which in the dried condition are known as tísu, késú, kesuda or palás-képpúl, have a bright orange colour, and, although they are much larger, closely resemble in appearance the common gorseflower (<em>Ulex europæus</em>) with which, indeed, they are botanically allied. Large quantities of the flowers are collected in March and April, and employed by the natives to produce a yellow dye, much used during the "Holi" festival. The dyeing operation, which consists in steeping the material in a hot or cold decoction of the flowers, is virtually a process of staining, because the colour can be readily washed out. On the other hand, a more permanent result is sometimes produced either by first preparing the cloth with alum and wood ash or by adding these substances to the dye-bath.</p>
<p>From the <em>Butea frondosa</em> is also obtained the so-called "Butea gum" or "Bengal kino," employed by the natives for tanning leather, and the tree is of additional interest because in many parts of India the lac insect (<em>Coccus lacca</em>) is reared upon it. This latter, as is well known, causes the formation of stick lac, from which shellac and lac dye are prepared.</p>
<p><em>Butin</em>, C<sub>15</sub>H<sub>12</sub>O<sub>5</sub>. The flowers are extracted with water, and the extract digested boiling with a little sulphuric acid. A light viscous precipitate devoid of dyeing property separates, and this is removed while hot and the filtrate left over-night. The clear liquid is now decanted from a small quantity of tarry substance, and partially evaporated on the water-bath. A further quantity of a black viscous precipitate thus separates, and when this has been removed the filtrate, after some days, deposits crystals of the colouring principle. For purification the product is dissolved in a little alcohol, the mixture poured into ether, and the solution well washed with water. The liquid is evaporated, and the residue repeatedly crystallised from dilute alcohol (Perkin and Hummel, Chem. Soc. Trans., 1904, 85, 1459).</p>
<p>[---]</p>
<p><span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;">* This result has been criticised by Goschker and Tambor, who by the employment of mordanted calico obtained from butin very weak shades. It is, however, certain that by the use of mordanted wool a conversion of butin into butein occurs.</span>Butin and butein dye mordanted woollen cloth identical shades, though as butin gives with an alcoholic lead acetate a practically colourless precipitate, it is not to be regarded as a colouring matter. In other words, butin is merely a colouring principle, and is converted during the dyeing operation by the action of the mordant into the colouring matter butein.*</p>
<p>The following shades are obtained: Chromium. Reddish-brown, <br />
Aluminium. Brick-red<br />
Tin. Full-yellow<br />
Iron. Brownish-black,<br />
and these are strikingly similar to those yielded by some of the hydroxybenzylidenecoumaranones artificially prepared by Friedlander and Rüdt (Ber., 1896, 29, 879) (see above).</p>
<p>The butea flowers contain but a trace of free butin or butein, and the glucoside present, which has not yet been isolated, is probably that of butin. This glucoside does not decompose readily during the dyeing process, hence the flowers do not dye mordanted cotton. In wool-dyeing, where acid-baths are employed, a better result is obtained, although in this case the shades possess but little strength. If the glucoside is first hydrolysed by boiling the flowers with dilute hydrochloric acid, or if sulphuric acid is employed, and the acid then neutralised with sodium carbonate, on evaporation a material is obtained which readily dyes by the usual methods. Such products give the following shades: with chromium, deep terra-cotta; with aluminium, a bright orange; with tin, bright yellow; and with iron, a brownish-olive. The chromium colour is characteristic, and is much redder in tint than that yielded by any known natural yellow dye.</p>Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-45765442893416388712023-11-10T10:17:00.003+02:002023-11-10T10:17:46.153+02:00Scoparin, Scutellarein(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p>
<p style="color:red;"><em>Cytisus scoparius</em> Jänönpapu, jänönvihma</p></span>
<p><strong><em>Scoparin</em></strong>, the colouring matter of the <em>Cytisus scoparius</em> (Link.), has been investigated by Stenhouse (Annalen, 78, 15), by Hlasiwetz (Annalen, 138, 190), and by Goldschmiedt and Hemmelmayer (Monatsh., 14, 202).</p>
<p>[---]</p>
<p><strong><em>Scutellarin</em></strong>. If the flowers and leaves of Scutellaria altissima are extracted with water the solution on keeping deposits crystals of <em>scutellarin</em>, C<sub>21</sub>H<sub>18</sub>O<sub>12</sub> (Molisch and Goldschmiedt, Monatsh., 1901, 22, 68; Goldschmiedt and Zerner, <em>ibid.</em>) 1910, 31, 439). It melts above 310, is sparingly soluble in the usual solvents, and the alcoholic solution gives with lead acetate a red precipitate, and with ferric chloride a green coloration passing into red on heating. With the haloid acids and sulphuric acid in the presence of acetic acid orange-red crystalline oxonium compounds separate, which are readily decomposed in contact with water.</p>
<p>[---]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-58175284265119389972023-11-07T19:29:00.001+02:002023-11-07T19:29:26.845+02:00Fukugi(CHAPTER V. The Flavone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>The Japanese dyestuff "fukugi" (botanical origin unknown) <span style="color:red;">[EDIT: <em>Garcinia subelliptica</em>]</span> has, at least until recently, been employed to a considerable extent in Japan as a mordant dyestuff. It consists of the wood of a tree which when ground forms an almost colourless powder, the extract of which is sold in the form of brittle rectangular cakes of a yellowish-brown colour.</p>
<p>Fukugetin, C<sub>17</sub>H<sub>12</sub>O<sub>6</sub>, the colouring matter, forms minute canary-yellow prismatic needles melting at 288-290° (Perkin and Phipps, Chem. Soc. Trans., 1904, 85, 58). It dissolves in alkaline solutions with a yellow colour, and gives with alcoholic lead acetate an orange-yellow precipitate and with alcoholic ferric chloride a brown-black coloration.</p>
<p>Crystalline acetyl and benzoyl derivatives of this colouring matter could not be obtained, but the bromine compound, C<sub>17</sub>H<sub>10</sub>O<sub>6</sub>Br<sub>2</sub>, minute flat needles, melting-point 280°, is readily prepared by the action of bromine on fukugetin in the presence of acetic acid. Fukugetin dyes mordanted fabrics shades which are almost identical with those given by luteolin - Chromium. Dull orange-yellow,<br />
Aluminium. Orange-yellow,<br />
Tin. Bright yellow, <br />
Iron. Olive brown,<br />
and resembles this colouring matter in that its alkaline solution is not oxidised on exposure to air. By fusion with alkali fukugetin gives <em>phloroglucinol</em> and <em>protocatechuic acid</em>.</p>
<p>The dyeing properties of "fukugi" are analogous to those of weld. The similarity in shade indeed is so marked that except in point of strength for fukugi is a stronger dye than weld it is impossible to distinguish between them.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-19865290204215948692023-11-05T20:50:00.002+02:002023-11-05T20:56:03.179+02:00Dyer's Broom.(CHAPTER V. The Flavone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p><em>Genista tinctoria</em>, Linn. {<em>Dyer's broom, Dyer's greenweed</em>; <em>Genet, Genestrole, Trentanel</em>, Fr.; <em>Ginster</em>, Ger.) is found in the pastures, thickets, and waste places throughout Central and Southern Europe, across Russian Asia to the Baikal, and northward to Southern Sweden. It is frequent in the greater part of England, but rare in Ireland and Scotland. The fact that it contains a yellow colouring matter is recorded by numerous writers, and the following embody the principal references to the dyeing and general properties of the plant: Bancroft ("Philosophy of Permanent Colours," 1813, 2, 108); Gmelin ("Handbook of Chemistry," 16, 517); Berthollet ("On Dyeing," 1824, 2, 242); Gonfreville ("L'Artdela Teinturedes Laines," 501); Leuchs ("Farben u. Farbekunde," 1846, 2, 309), and Schützenberger ("Traite des Matieres Colorantes," 1867, 4, 422).</p>
<p>To isolate the colouring matters, a hot aqueous extract of the plant is treated with lead acetate solution, and the pale yellow viscous precipitate is collected and decomposed by means of boiling dilute sulphuric acid. The clear liquid decanted from the lead sulphate deposits on cooling a dull yellow powder; this is filtered off, dissolved in a little alcohol, and the solution poured into a large volume of ether, causing the separation of a dark-coloured resinous impurity. The clear liquid is evaporated, yielding a yellow crystalline residue, which consists of two substances. To separate these, advantage is taken of the fact that, with sulphuric acid in the presence of acetic acid, one only of these compounds gives an insoluble sulphate. This is collected and decomposed with water and the product crystallised from dilute alcohol. It is obtained as yellow needles, and was found to be identical with the <em>luteolin</em> of weld (<em>Reseda luteola</em>) (Perkin and Newbury, Chem. Soc. Trans., 1899, 75, 830).</p>
<p><em>Genistein</em>, C<sub>14</sub>H<sub>10</sub>O<sub>5</sub>, the second colouring matter of dyer's broom, is present in the mother liquors obtained during the purification of the luteolin, and also in considerable quantity in the filtrate from the lead precipitate, from which it is most readily isolated. To the boiling liquid ammonia is added, causing the separation of a lemonyellow precipitate, which is collected and decomposed with boiling dilute sulphuric acid. The clear liquid is extracted with ether, and the extract evaporated, leaving a brownish crystalline mass. It is purified by crystallisation from acetic acid, and by conversion into the acetyl derivative.</p>
<p>Genistein crystallises in long colourless needles; melting-point 291-293° (Perkin and Horsfall, Chem. Soc. Trans., 1900, 77, 1312); soluble in alkalis with a pale yellow coloration. Alcoholic ferric chloride gives a dull-red violet coloration, and alcoholic basic lead acetate a lemon-yellow precipitate.</p>
<p><em>Triacetylgenistein</em>, C<sub>14</sub>H<sub>7</sub>O<sub>5</sub>(C<sub>2</sub>H<sub>3</sub>O)<sub>3</sub>, colourless needles, melting-point, 197-201°; and <em>tetrabromgenistein</em>, C<sub>14</sub>H<sub>6</sub>Br<sub>4</sub>O<sub>5</sub>, colourless needles, melting-point above 290°, have been described.</p>
<p>On digestion with boiling 50 per cent, potassium hydroxide, genistein gives <em>phloroglucinol</em> and <em>p-hydroxyphenylacetic acid</em>.</p>
<p>By methylation with methyl iodide in the usual manner, genistein dimethyl ether and methylgenistein dimethyl ether are produced.</p>
<p>Genistein dimethyl ether, C<sub>14</sub>H<sub>8</sub>O<sub>3</sub>(OCH<sub>3</sub>)<sub>2</sub>, forms colourless leaflets, melts at 137-139°, and gives the monacetyl compound, C<sub>14</sub>H<sub>7</sub>O<sub>3</sub>(C<sub>2</sub>H<sub>3</sub>O)(OCH<sub>3</sub>)<sub>2</sub>, minute colourless needles, melting-point 202-204°. When decomposed with alcoholic potash, it forms <em>methoxyphenylacetic acid</em> and <em>phloroglucinol-monomethyl ether</em> (identified by means of its disazobenzene derivative).</p>
<p><em>Methylgenistein dimethyl ether</em>,<br />
CH<sub>3</sub>.C<sub>14</sub>H<sub>7</sub>O<sub>3</sub>(OCH<sub>3</sub>)<sub>2</sub>, melts at 202°; and the acetyl derivative,<br />
CH<sub>3</sub>.C<sub>14</sub>H<sub>6</sub>O<sub>3</sub>(C<sub>2</sub>H<sub>3</sub>O)(OCH<sub>3</sub>) <sub>2</sub>,<br />
forms colourless needles, melting-point 212-214°. With alcoholic potash it gives <em>methoxyphenylacetic acid</em> and probably <em>methylphloroglucinol-monomethyl ether</em>.</p>
<p><em>Genistein diethyl ether</em>, C<sub>14</sub>H<sub>8</sub>O<sub>3</sub>(OC<sub>2</sub>H<sub>5</sub>)<sub>2</sub>, forms colourless needles, melting-point 132-134°; whereas acetylgenistein diethyl ether, C<sub>14</sub>H<sub>7</sub>O<sub>3</sub>(C<sub>2</sub>H<sub>3</sub>0)(OC<sub>2</sub>H<sub>5</sub>)<sub>2</sub>, melts at 168-170°. Alcoholic potash gives <em>p-ethoxyphenylacetic acid</em>.</p>
<p>According to Perkin and Horsfall, genistein is most probably a <em>trihydroxyphenylketocumaran</em>.</p>
<p>Genistein is a feeble colouring matter, and upon woollen cloth gives, with chromium mordant, a pale greenish-yellow; with aluminium mordant, a very pale yellow; and with iron mordant, a chocolate- brown shade.</p>
<h3>Dyeing Properties of Dyer's Broom.</h3>
<p>-In this respect there is a close resemblance between dyer's broom and weld. The dyeing power of the former is distinctly the weaker of the two; otherwise the only point of difference worthy of mention is that shown by the iron mordant, which, in the case of dyer's broom, gives a duller and more drab-coloured shade. Luteolin is also present in the <em>Digitalis purpurea</em> (digito-flavone), (Fleischer and Fromm, Ber., 1899, 32, 1184; v. Kostanecki and Diller, <em>ibid.</em>) 1901, 34, 3577), and in the flowers of <em>Antirrhinum majus</em> (Wheldaleand Bassett, Biochem. Jour., <em>loc. cit.</em>).</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-12090454227962507422023-11-03T17:35:00.006+02:002023-11-03T17:36:47.124+02:00Weld(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Weld is the dried herbaceous plant known as <em>Reseda luteola</em> formerly cultivated to a considerable extent in France, Germany, and Austria. Its cultivation in this country has nearly ceased, because not only is the quantity of colouring matter it contains very small, but the carriage of the plant, owing to its bulky nature, is expensive. A special interest, however, attaches to weld, for it is said to be the oldest European dyestuff known, and was used by the Gauls and other nations dwelling north of the Alps in the time of Julius Caesar.</p>
<p>The plant attains a height of about 3 feet, is pale brown in colour, and is sold in sheaves like straw. The colouring matter is disseminated throughout the entire plant, but the greater quantity occurs in the upper extremity and the seeds.</p>
<p><em>Luteolin</em>, the main colouring matter of weld, was examined by Chevreul (J. Chim. Med, 6, 157; Annalen, 82, 53), who obtained it in a crude condition; its isolation in a state of chemical purity was first achieved by Moldenhauer (Annalen, 100, 180), who assigned to it the formula C<sub>20</sub>H<sub>14</sub>O<sub>8</sub>. It was subsequently investigated by Schützenberger and Paraf (Bull. Soc. Chim., 1861, (i.), 18), who proposed the formula C<sub>12</sub>H<sub>8</sub>O<sub>5</sub> and purified it in a somewhat novel manner which is worthy of mention. Weld was exhausted with alcohol, the extract evaporated, and treated with water, which threw down a dirty greenish precipitate. This was collected, introduced with a little water into a sealed tube and heated to 250°. On cooling the sides of the tube were found to be coated with golden-yellow needles of luteolin, and the impurities had collected at the bottom of the tube to form a resinous cake.</p>
<p>Hlasiwetz suggested that luteolin had the formula C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> and was isomeric with the paradiscetin, which he obtained during the fusion of quercetin with alkali (Annalen, 112, 107).</p>
<p>For the preparation of luteolin in quantity, Perkin (Chem. Soc. Trans., 1896, 69, 206, 799) employs weld extract.</p>
<p>300 gms. of the extract dissolved in 3 litres of water is treated with 100 c.c. of hydrochloric acid (33 per cent.), and the mixture is digested at the boiling temperature for some hours. A quantity of a black resinous substance separates, which is collected while hot, and the filtrate, which contains the colouring matter, is allowed to stand for twelve hours. A brown precipitate of impure luteolin is slowly deposited, and is collected, washed, and dissolved in a little hot alcohol. On pouring this solution into ether, the main bulk of the impurity is precipitated, and the ethereal liquid on evaporation yields a yellow residue, which is crystallised from dilute alcohol. The product in addition to luteolin contains apigenin (Chem. Soc. Trans., 1900, 77, 1315), and the latter can only be removed with certainty by the following method: -</p>
<p>The mixture dissolved in boiling glacial acetic acid is treated with a few drops of strong hydrochloric acid; this causes the almost immediate separation of luteolin as hydrochloride, whereas the apigenin remains in solution. The hydrochloride is collected, decomposed by water, and the luteolin crystallised from dilute alcohol.</p>
<p>[---]</p>
<p>It has already been stated that weld contains a second colouring matter, Apigenin (v. Parsley).</p>
<h3>Dyeing Properties of Weld.</h3>
<p>The importance of weld as a dyestuff in silk and wool dyeing has greatly diminished in consequence of its low colouring power compared with quercitron bark, flavin, and old fustic. This in one respect is unfortunate, because, of all the natural yellow colouring matters, it yields the purest and fastest shades. In conjunction with aluminium and tin mordants it gives very bright pure lemon-yellow colours, and these do not change to an olive or reddish tint as in the case with other vegetable yellows. With chromium and iron mordants weld gives yellowish and greenish olives respectively. For yellow, wool and silk are mordanted with alum and tartar in the usual manner and dyed subsequently in a decoction of weld with the addition of chalk to the dye-bath. Weld alumina yellow is to some extent still employed in this country for certain army cloths and braid. For silk dyeing, weld extract is manufactured in small quantity, and is used for the production of yellow and olive colours.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-74887847591715276412023-11-02T19:30:00.001+02:002023-11-02T19:30:19.244+02:00Lotus arabicus(CHAPTER V. The Flavone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>The <em>L. arabicus</em> (Linn.) is a leguminous plant, indigenous to Egypt and Northern Africa, and in the young condition is extremely poisonous. It has been investigated by Dunstan and Henry (Phil. Trans., 1901, 194, 515).</p>
<p><em>Lotusin</em>, the active principle, can be isolated by extracting the dried plant with methyl alcohol. The extract is evaporated, the residue treated with water to remove chlorophyll and resin, and from the aqueous solution tannin and other impurities are precipitated by means of lead acetate. The nitrate, on evaporation, leaves a syrupy residue, from which crystals of lotusin slowly separate. In the pure condition lotusin, C<sub>28</sub>H<sub>31</sub>NO<sub>16</sub>, forms yellow needles, and when hydrolysed by digestion with hydrochloric acid, or by means of an enzyme <em>lotase</em>, also found in the plant, yields dextrose, <em>lotoflavin</em>, and hydrocyanic acid, according to the following equation:<br />
C<sub>28</sub>H<sub>31</sub>O<sub>16</sub>N + 2H<sub>2</sub>O = 2C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> + C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> + HCN</p>
<p>When warmed with alcoholic potash (20 per cent.) lotusin is gradually decomposed with production of ammonia and <em>lotusinic acid</em>:<br />
C<sub>28</sub>H<sub>31</sub>O<sub>16</sub>N + 2H<sub>2</sub>O = C<sub>28</sub>H<sub>32</sub>O<sub>18</sub> + NH<sub>3</sub> (Lotusinic acid.)</p>
<p>This compound is monobasic, gives yellow crystalline salts, and is hydrolysed by dilute hydrochloric acid with formation of <em>lotoflavin dextrose</em> and <em>heptogluconic acid</em>:<br />
C<sub>28</sub>H<sub>32</sub>O<sub>18</sub> + 2H<sub></sub>2 = C<sub>15</sub>H<sub>10</sub>O<sub>6</sub>; + C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> + C<sub>7</sub>H<sub>14</sub>O<sub>8</sub></p>
<p>Lotoflavin, C<sub>15</sub>H<sub>10</sub>O<sub>6</sub>, crystallises in yellow needles, soluble in alkaline solutions with a yellow colour. By fusion with alkali, <em>phloroglucinol</em> and <em>β-resorcylic acid</em> are produced.</p>
<p>With acetic anhydride lotoflavin gives a <em>tetra-acetyl</em> compound, C<sub>15</sub>H<sub>6</sub>O<sub>6</sub>(C<sub>2</sub>H<sub>3</sub>O)<sub>4</sub>, colourless needles, melting-point 176-178°, and when methylated by means of methyl iodide the <em>trimethyl ether</em>, C<sub>15</sub>H<sub>7</sub>O<sub>3</sub>(OCH<sub>3</sub>)<sub>3</sub>, is obtained. This latter compound exists in two forms, viz. the a-form yellow rosettes, melting-point 125°, and the -form glistening needles, melting-point 175°, which are mutually convertible. Both varieties give by means of acetic anhydride the same <em>monoacetyl-lotoflavin trimethyl ether</em>, C<sub>15</sub>H<sub>6</sub>O<sub>3</sub>(C<sub>2</sub>H<sub>3</sub>O)(OCH<sub>3</sub>)<sub>3</sub>, yellow needles, melting-point 147°.</p>
<p>According to Dunstan and Henry, lotoflavin is probably a <em>tetrahydroxyflavone</em>, possessing the formula [KUVA PUUTTUU]</p>
<p>The hydrolysis of the cyanogenetic glucoside lotusin, with formation of maltose, lotoflavin and hydrocyanic acid, may be expressed by the equation<br />
C<sub>28</sub>H<sub>31</sub>NO<sub>16</sub> + H<sub>2</sub>O = C<sub>12</sub>H<sub>22</sub>O<sub>11</sub> + C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> + HCN</p>
<p>The following constitutions are respectively assigned to lotusin (1) and lotusinic acid (2): [KUVA]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-42321129421133450472023-11-01T16:52:00.004+02:002023-11-01T16:52:52.290+02:00Saponaria officinalis(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>The epidermal cells of the leaves of certain flowering plants contain, dissolved in their cell sap, a substance which is coloured blue by iodine. The colour disappears on warming and returns on cooling, as is the case with starch. On this account the compound was regarded as an amorphous variety of starch by Sanio, its discoverer (Botanische Zeitung, 1857, 15, 420). Schenck (<em>ibid.</em>, 1857, 15, 497, 455) doubted whether this substance was identical with starch, and the correctness of this view was confirmed by Nageli (Beitrage zur wissensch. Botanik, 1860, 2, 187). For the chemical examination of this substance the dried shoots of the <em>S. officinalis</em> were selected by Barger (Chem. Soc. Trans., 1906, 89, 1210) as the raw material, because this plant is relatively rich in the compound, and is grown on the Continent for pharmaceutical purposes, so that large quantities are easily obtainable.</p>
<p>[---]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-53118978214447638302023-10-30T12:50:00.001+02:002023-10-30T13:08:39.882+02:00Vitex littoralis(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p>
<p style="color:red;"><em>Vitex littoralis</em> = <em>Vitex lucens</em></p></span>
<p>The Vitex littoralis (A. Cunn.) or "Puriri" is a large tree, 40-60 feet high, and 3-5 feet in diameter, which grows only in the northern portion of the North Island of New Zealand. The wood affords a very durable timber, and is chiefly used for house blocks, fencing posts, piles for bridges, railway sleepers, etc.</p>
<p><em>Vitexin</em>, the main colouring matter, is present in the wood in the form of a glucoside which has not yet been isolated. It is prepared by digesting a purified extract of the dyestuff with boiling dilute hydrochloric acid, and by this means separates in the form of a yellow viscous mass. By extracting this crude product with boiling alcohol, a pale yellow crystalline powder remains undissolved, and this, owing to its sparing solubility, is most readily purified by acetylation, and the subsequent hydrolysis of the pure acetyl derivative (Perkin, Chem. Soc. Trans., 1898, 74, 1020).</p>
<p>[---]</p>
<p>[---] Vitexin is a somewhat feeble colouring matter, and dyes shades similar to those given by apigenin; these, employing woollen cloth mordanted with chromium, aluminium, and tin, are respectively greenish-yellow, pale bright yellow, and pale brown.</p>
<p>In addition to vitexin the wood of the <em>Vitex littoralis</em> contains (as glucoside) a small quantity of a second colouring matter, homovitexin. It was obtained as a pale yellow powder, melting-point 245-246°, and is distinguished from vitexin by its ready solubility in alcohol. Fused with alkali it gives phloroglucinol and <em>p</em>-hydroxybenzoic acid, and is possessed of feeble dyeing property. The analytical figures approximate to C<sub>16</sub>H<sub>16</sub>O<sub>7</sub> or C<sub>18</sub>H<sub>18</sub>O<sub>8</sub>.</p>
<p>According to Barger (Chem. Soc. Trans., 1906, 89, 1120) the glucoside saponarin, which is present in <em>Saponaria offirinalis</em> (Linn.), yields on hydrolysis glucose, saponaretin, and a small quantity of vitexin. It is possible that saponaretin and homovitexin are identical.</p>Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-29402559099011285512023-10-29T17:20:00.004+02:002023-10-29T17:20:55.736+02:00Robinia pseud-acacia(CHAPTER V. The Flavone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p><em>Acacetin</em>, C<sub>16</sub>H<sub>12</sub>O<sub>5</sub>, the colouring matter of the leaves of the <em>Robinia pseud-acacia</em> (Linn.) (common or false acacia, North American locust), forms almost colourless needles, soluble in alkalis with a pale yellow coloration (Perkin, Chem. Soc. Trans., 1900, 71, 430.</p>
<p>To prepare it a boiling aqueous decoction of the leaves is treated with basic lead acetate solution, and the pale yellow precipitate is suspended in water and decomposed with boiling dilute sulphuric acid. From the clear liquid the colouring matter is removed by extraction with ether and purified by crystallisation from dilute alcohol.</p>
<p>Acacetin forms a diacetyl derivative, C<sub>16</sub>H<sub>10</sub>O<sub>5</sub>(C<sub>2</sub>H<sub>3</sub>O)<sub>2</sub>, colourless needles, melting-point 195-198°, and when fused with alkali gives phloroglucinol and <em>p</em>-hydroxybenzoic acid. Digested with boiling hydriodic acid it yields apigenin and one molecule of methyl iodide, and is consequently an <em>apigenin monomethylether</em>. Acacetin is very probably identical with von Gerichten's apigenin methyl ether (Ber., 1900, 33, 2908) - the acetyl derivative of which melts at 198-200°.</p>
<p>Interesting is the fact that the flowers of the <em>Robinia pseud-acacia</em> contain robinin, a glucoside of the trihydroxy flavonol kaempferol - which contains one more hydroxyl than apigenin. This is referred to later.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-2980825621241627432023-10-28T13:59:00.005+03:002023-10-28T13:59:54.054+03:00Chamomile Flowers(CHAPTER V. The Flavone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Anthemis Nobilis. An examination of the flowers of Anthemis nobilis (Linn.) by Power and Browning (Chem. Soc. Trans., 1914, 105, 1833) has shown that these contain in addition to numerous other substances an apigenin glucoside, C<sub>21</sub>H<sub>20</sub>O<sub>10</sub>.2H<sub>2</sub>O, faintly yellow microscopic crystals melting at 178-180°. It dissolves in alkalis with a yellow colour and gives with aqueous ferric chloride a purplish-brown coloration. Dried at 125-130° it loses one molecule of water of crystallisation, but the second molecule cannot be eliminated without decomposing the substance. This is evident from the composition of the hexa-acetyl derivative, C<sub>21</sub>H<sub>14</sub>O<sub>10</sub>(COCH<sub>3</sub>)<sub>6</sub>, colourless microscopic crystals, melting-point 144-146°, the molecule of water in question being eliminated in the process of acetylation.</p>
<p>By digestion with 5 per cent, aqueous sulphuric acid for three hours, this glucoside yields apigenin and dextrose according to the equation -<br />
C<sub>21</sub>H<sub>20</sub>O<sub>10</sub>, H<sub>2</sub>O = C<sub>15</sub>H<sub>10</sub>O<sub>5</sub> + C<sub>6</sub>H<sub>12</sub>O<sub>6</sub></p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-37475737755037783732023-10-27T17:05:00.003+03:002023-10-27T17:05:39.011+03:00Parsley (Apiin, apigenin)(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918<br />
<br />
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p>
<p style="color:red;"><em>Carum petroselinum</em> = <em>Petroselinum crispum</em> = persilja</p></span>
<p><em>Apiin</em>, the glucoside of apigenin, is found in the leaves, stem, and seeds of parsley (<em>Carum (Apium) petroselinum</em>, Benth. and Hook.), (Rump, Buchner's Repert. f. Pharm., 1836, 6, 6; Braconnot, Ann. Chim. Phys., 1843, iii., 9, 250). [---]</p>
<p>[---]</p>
<p>Apigenin closely resembles chrysin in its tinctorial properties, although it is a somewhat stronger dyestuff. The shades it gives upon wool mordanted with aluminium, chromium, and iron are respectively pure yellow, weak yellow-orange, and chocolate-brown.</p>
<p>Apigenin is also present in weld (<em>Reseda luteola</em>), (Perkin and Horsfall, Chem. Soc. Trans., 1900, 77, 1314), in the flowers of <em>Antirrhinum majus</em> (Wheldale and Bassett, Biochem. Jour., 1913, 7, 441), and exists probably also in chamomile flowers (Perkin).</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-17802263342254062502023-10-27T11:30:00.003+03:002023-10-27T11:30:47.586+03:00Poplar Buds(CHAPTER V. The Flavone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p><em>Chrysin</em>, C<sub>15</sub>H<sub>10</sub>O<sub>4</sub>, is contained in the leaf buds of the poplar (<em>Populus pyramidalis</em>, Salisb., <em>P. nigra</em>, Linn., <em>P. monilifera</em>, Ait.), in which it is present to the extent of about ¼ per cent. It was first isolated by Piccard (Ber., 6, 884, 1160; 7, 888; 10, 176) and is best prepared by the method devised by this chemist.</p>
<p>An alcoholic extract of 1000 grams of poplar buds is treated while hot with about 120 grams of lead acetate, and after standing for some time the yellow precipitate is removed. Through the clear filtrate sulphuretted hydrogen is passed in order to decompose lead salts, the sulphide of lead is filtered off and the liquid evaporated to dryness. The residue dissolved in a little hot alcohol gradually deposits crystals ofchrysin, which are collected, successively extracted with carbon disulphide, benzene, and boiling water, and finally crystallised two or three times from alcohol.</p>
<p>[---]</p>
<p>Chrysin is a feeble dyestuff. The shades produced on wool mordanted with aluminium, chromium, and iron, are respectively pale bright yellow, pale yellow-orange, and chocolate-brown.</p>
<p><em>Tectochrysin</em>, a second constituent of poplar buds, is present in the benzene extracts from the crude chrysin. Tectochrysin is <em>chrysin</em> <em>monomethylether</em>, (C<sub>15</sub>H<sub>9</sub>O<sub>3</sub>.OCH<sub>3</sub>), (Piccard), and is identical with the methylation product of chrysin itself (<em>loc. cit.</em>).</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-67356643015379474672023-10-26T11:39:00.002+03:002023-10-26T11:39:33.628+03:00Natural Flavone(CHAPTER V. The Flavone Group.)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Very interesting is the occurrence of flavone in nature (Müller, Chem. Soc. Trans., 1915, 107, 872). It is well known that many varieties of the primula possess on their flower stalks, leaves, and seed capsules a characteristic dust termed by gardeners "meal" or "farina," and this is most pronounced on varieties recently obtained from China and Japan. This powder, examined by Hugo Müller who obtained it mainly from the [Primula] <em>P. pulverulenta</em> and <em>P. japonica</em>, dissolves readily in benzene and boiling ligroin, and the concentrated solution on cooling became semi-solid owing to the separation of crystalline tufts.</p>
<p>It possessed the formula C<sub>15</sub>H<sub>10</sub>O<sub>2</sub>, melted at 99-100°, and on boiling with dilute sodium hydroxide gave slowly a yellow solution, with formation of a small quantity of acetophenone, and the latter could be obtained in greater quantity by the action of methyl alcoholic sodium hydroxide. Employing methyl alcoholic barium hydroxide, a reagent not previously suggested for the degradation of flavone compounds, Müller obtained a substance C<sub>15</sub>H<sub>12</sub>O<sub>3</sub>. This by the action of alkalis was converted into salicylic acid and acetophenone and evidently consisted of hydroxy-benzoyl-acetophenone (0-hydroxy-dibenzoyl-methane)<br />
OH.C<sub>6</sub>H<sub>4</sub>.CO.CH<sub>2</sub>.CO.C<sub>6</sub>H<sub>5</sub></p>
<p>The compound C<sub>15</sub>H<sub>10</sub>O<sub>2</sub> was thus without doubt <em>flavone</em>, and it is interesting to note that though hydroxybenzoyl-acetophenone was assumed by Feuerstein and v. Kostanecki (Ber., 1898, 31, 1758) to be the first product of the hydrolysis of this substance, its isolation in this manner had not previously been effected.</p>
<p>The function which flavone exercises in the economy of the plant life of the primula is difficult to explain, though it may be of service on account of its repellent action towards water.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-77239411742554849302023-10-25T16:06:00.000+03:002023-10-25T16:06:07.735+03:00Gentian Root(CHAPTER IV. The Xanthone Group.) <span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>The <em>Gentiana lutea</em> (Linn.), from which the gentian root is derived, chiefly occurs in mountainous districts, especially in Switzerland and the Tyrol. There is present in the root of this and other species of <em>gentiana</em> a bitter principle which is said to possess valuable tonic virtues, and on this account some quantity of the material is imported into this country for medicinal purposes.</p>
<p><strong><em>Gentisin</em></strong>, the colouring matter of gentian root, was first isolated by Henry and Caventou (J. Pharm. Chim., 1821, 178), and was shown by Baumert (Annalen, 62, 106) to possess the formula C<sub>14</sub>H<sub>10</sub>O<sub>6</sub>. Hlasiwetz and Habermann (<em>ibid.</em>, 175, 63; 180, 343), somewhat later, found that gentisin contains two hydroxyl groups, and that, when fused with potassium hydrate, phlorglucinol and gentisic acid (hydroquinone carboxylic acid) are produced from it. By the action of hydrochloric acid on gentisin, methyl chloride was evolved, a probable indication of the presence of a methoxy group. To prepare gentisin (Baumert, <em>loc. cit.</em>}, the root is well washed with water, then extracted with alcohol, and the extract evaporated to a small bulk. The residue is washed with water to remove the bitter principle, and then with ether to extract plant wax. For purification, the crude colouring matter is repeatedly crystallised from alcohol; 10 kilos, of the root yield about 4 grams of the substance. Gentisin crystallises in yellow needles, is sparingly soluble in alcohol, and dissolves in alkaline solutions with a yellow colour.</p>
<p><strong><em>Gentisein</em></strong>, C<sub>13</sub>H<sub>8</sub>O<sub>5</sub>, 2H<sub>2</sub>O. When gentisin is digested with boiling hydriodic acid, it is converted into gentisein with evolution of i molecule of methyl iodide. Gentisein consists of straw-yellow needles, melting at 315°, and gives with sodium amalgam a bloodred coloration, whereas gentisin, by a similar method, yields a deep green coloured liquid (v. Kostanecki, Monatsh., 12, 205). By the action of acetic anhydride, gentisein is converted into the <em>triacetyl derivative</em>, C<sub>13</sub>H<sub>5</sub>O<sub>5</sub>(C<sub>2</sub>H<sub>3</sub>O)<sub>3</sub>, needles, melting-point 226° (v. Kostanecki, <em>loc. cit.</em>}; but on methylation with methyl iodide, a <em>dimethyl ether</em>, C<sub>13</sub>H<sub>5</sub>O<sub>2</sub>(OH)OCH<sub>3</sub>)<sub>2</sub>, yellow needles, melting-point 167°, is produced (v. Kostanecki and Schmidt, Monatsh., 12, 318).</p>
<p>Partial methylation converts gentisein into gentisin, and it is thus certain that the latter consists of <em>gentisein monomethyl ether</em>. v. Kostanecki and Tambor (Monatsh., 15, 1) obtained gentisein by distilling a mixture of phloroglucinol and hydroquinone carboxylic acid with acetic anhydride and its constitution is therefore represented as 1:3:7 trihydroxyxanthone. By a study of disazobenzene-gentisin, C<sub>14</sub>H<sub>8</sub>O<sub>5</sub>(C<sub>6</sub>H<sub>5</sub>N<sub>2</sub>)<sub>2</sub>, scarlet-red needles, melting-point 251-252° (Perkin, Chem. Soc. Trans., 73, 1028), which gives the <em>diacetyl</em> derivative,<br />
C<sub>14</sub>H<sub>6</sub>O<sub>5</sub>(C<sub>2</sub>H<sub>3</sub>0)<sub>2</sub>(C<sub>6</sub>H<sub>5</sub>N<sub>2</sub>)<sub>2</sub>,<br />
orange-red needles, melting-point 218-220°, it has been shown that gentisin itself possesses the constitution. As gentisin yields by means of methyl iodide only a monomethyl ether, the original methoxy group cannot be in the position (1). On the other hand, if gentisin is represented by the formula (2) [KUVAT PUUTTUVAT], the azobenzene groups would enter the positions 4 and 2, and from such a compound an acetyl derivative cannot be obtained in the ordinary manner (compare disazobenzene phloroglucinol).</p>
<p>Gentisin is a feeble dyestuff, and gives on wool mordanted with chromium, aluminium, and tin, respectively, pale green-yellow, pale bright yellow, and very pale cream-coloured shades (Perkin and Hummel, Chem. Soc. Trans., 1896, 69, 1290).</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-25455812298193797072023-10-25T11:55:00.000+03:002023-10-25T11:55:53.007+03:00Indian Yellow (Euxanthone).(CHAPTER IV. The Xanthone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Indian yellow, Piuri, Purree, or Pioury, is a pigment mainly used in India for colouring walls, doors, and lattice-work, and by artists for water-colour work. On account of its disagreeable smell it is but rarely employed as a dyestuff. It is, or was, made almost exclusively at Monghyr in Bengal, and is obtained from the urine of cows which have been fed upon mango leaves. On heating the urine, usually in an earthen pot, the colouring matter separates out; this is pressed into a ball and dried partly over a charcoal fire and finally in the sun. It sold on the spot at about 1 rupee per lb. and is, or was, mainly sent to Calcutta and Patna. One cow produces, on the average, 3.4 litres of urine per diem, yielding 2 oz. (56 grams) of piuri. The yearly production is stated to have been from 100 to 150 cwts., which was probably over-estimated (v. Journ. Soc. Arts, 1883, (v.), 32, 16, and Annalen, 254, 268).</p>
<p>Piuri occurs in commerce in the form of round balls, which internally are of a brilliant yellow colour, whereas the outer layers are either brown or of a dirty green colour. The substance has a characteristic urinous smell. The undecomposed part consists only of <em>euxanthic acid</em> (C<sub>19</sub>H<sub>18</sub>O<sub>11</sub>) in the form of a magnesium or calcium salt; the outer and decomposed portion contains in addition euxanthone, both free and combined. The composition of piuri seems to be variable; a fine sample, according to Graebe, contained<br />
Euxanthic acid … 51.0<br />
Silicic acid and alumina … 1.5<br />
Magnesium … 4.2<br />
Calcium … 3.4<br />
Water and volatile matter … 39.0<br />
[total] 99.1</p>
<p>[---]</p>
<p>Euxanthone possesses only feeble tinctorial properties; the respective shades obtained with woollen cloth mordanted with chromium, aluminium, and tin being dull brown-yellow, pale bright yellow, and very pale bright yellow (Perkin and Hummel, Chem. Soc. Trans., 1896, 69, 1290).</p>Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-38953572721682295512023-10-24T18:40:00.001+03:002023-10-24T18:40:09.140+03:00Maclurin(CHAPTER III. The Benzophenone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>This substance occurs, together with morin, in the wood of the tropical tree <em>Chlorophora tinctoria</em> (Gaudich), which comes into commerce as "Old Fustic".</p>
<p>The colouring matters of old fustic were first investigated by Chevreul ("Lemons de chimie applique a la teinture," ii., 150), who described two substances, one sparingly soluble in water, calledmorin, and a second somewhat more readily soluble. Wagner (Jour. f. pr. Chemie, (i), 51, 82) termed the latter <em>moritannic acid</em>) and considered that it had the same percentage composition as morin. Hlasiwetz and Pfaundler (Annalen, 127, 351), on the other hand, found that the so-called moritannic acid was not an acid, and as moreover its composition and properties were quite distinct from those of morin, they gave it the name "Maclurin". </p>
<p>When morin is precipitated from a hot aqueous extract of old fustic by means of lead acetate the solution contains maclurin. After removal of lead in the usual manner, the liquid is partially evaporated and extracted with ethyl acetate, which dissolves the colouring matter. The crude product is crystallised from hot water or dilute acetic acid (Perkin and Cope, Chem. Soc. Trans., 1895, 67, 943). A crude maclurin is also obtained during the preparation of fustic extract, partly in the form of its calcium salt, and this product may be purified with dilute hydrochloric acid and crystallised from water. In order to decolorise the crystals, acetic acid is added to a hot aqueous solution and a little lead acetate in such quantity that no precipitate is formed, and the solution is then treated with sulphuretted hydrogen. The clear liquid thus obtained is much less strongly coloured, and after repeating the operation two or three times, the maclurin, which crystallises out on standing, possesses only a pale yellow tint.</p>
<p><strong><em>Maclurin</em></strong>, to which the composition C<sub>13</sub>H<sub>10</sub>O<sub>6</sub> was assigned by Hlasiwetz and Pfaundler (Jahresber., 1864, 558), consists, when pure, of almost colourless needles, which contain one molecule of water of crystallisation; the anhydrous compound melts at 200°C. (Wagner, Jahresber., 1850,529). The colouring matter is somewhat soluble in boiling water, is soluble in aqueous alkalis, forming pale yellow solutions, whilst with ferric chloride its aqueous solutions give a greenish-black coloration, and with aqueous lead acetate a yellow precipitate, which is soluble in acetic acid. When boiled with potassium hydroxide maclurin yields phloroglucinol and protocatechuic acid.</p>
<p>[---]</p>
<h3>Patent Fustin.</h3>
<p>Under the name "patent fustin" a colouring matter has been placed on the market, which consists chiefly of diazobenzene-maclurin (C. S. Bedford, 1887; Eng. Pat. 12667). To prepare this substance, old fustic is extracted with boiling water, the solution is decanted from the precipitate of morin and its calcium salt which separates on cooling, and is neutralised with the necessary quantity of sodium carbonate. Diazobenzene sulphate is then added until a precipitate no longer forms, and this is collected and washed with water. It is sold in the form of a paste, and dyes chrome mordanted wool an orange-brown shade.</p>
<p><strong><em>Diazobenzene-maclurin</em></strong> (Bedford and Perkin, Chem. Soc. Trans., 1895, 67, 933; <em>ibid.</em>, 1897, 71, 186), which crystallises in salmon-red prismatic needles, melting-point 270°C. (decomp.), has the following constitution: [KUVA PUUTTUU]</p>
<p>It dyes wool and silk direct from a weakly acid bath, in shades of orange, and on mordants gives colours varying from orange-red on aluminium and orange-brown on chromium, to olive on iron. The dyeings are fairly fast to washing.</p>
<p>---</p>
<h3>Dyeing Properties of Maclurin.</h3>
<p>With aluminium mordant maclurin gives a pale yellow, with chromium a yellow-green, and with iron a weak grey colour may be obtained.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-81557399145226877032023-10-23T18:25:00.004+03:002023-10-23T18:25:55.752+03:00Phloretin(CHAPTER III. The Benzophenone Group.)(Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Phloretin occurs in the form of two distinct glucosides, phloridzin and glycyphyllin, which are found in the root-bark of the apple, cherry, and plum-tree, and in the leaves of <em>Smilax glycyphylla</em> respectively (cf. Rennie, Jour. Chem. Soc., 1887, 634); whilst by catalytic hydrogenation of naringenin, in alcoholic solution with palladous chloride and hydrogen, Franck (Beitr. Phys., 1, 179; cf. Chem. Centrbt., 1914, ii., 253) obtained a dihydro-naringenin which he considered to be identical with phloretin.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-84620160918362517002023-10-23T13:06:00.001+03:002023-10-23T13:06:07.299+03:00Cotoïn. (Osa artikkelista)(CHAPTER III. The Benzophenone Group.)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>Cotoïn can be isolated from true Coto bark by extracting the powdered bark with cold ether, distilling off the ether from the extract, and mixing the residue, whilst still hot, with light petroleum, whereupon a resinous-oily mass separates, from which the solution of cotoïn can be decanted and the product obtained from it in the form of large yellow crystals. A further quantity can be obtained from the resinous mass mentioned above by boiling it with lime-water, and treating the solution obtained with hydrochloric acid, when the cotoïn is precipitated. Cotoïn may be recrystallised from alcohol, or hot water, when it separates in yellow prisms, melting-point 130-131°C. It is difficultly soluble in cold water, readily soluble in hot, is fairly soluble in alcohol, ether, and chloroform, but sparingly soluble in light petroleum or benzene. It dissolves in alkalis forming yellow solutions from which it is reprecipitated on acidification. As decomposition products of cotoïn, phloroglucinol as also benzoic acid have been obtained.</p>
<p>[---]</p>
<p>A number of poly-hydroxy benzophenone derivatives, including products found in Coto bark and related to cotoïn, have been prepared by W. H. Perkin and Robinson (Proc. Chem. Soc., 1906, 305).</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-15852134083909339932023-10-22T17:14:00.003+03:002023-10-22T17:14:39.186+03:00CHAPTER III. The Benzophenone Group.Introduction. (Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<h3>Introduction</h3>
<p>THIS group contains but one product, maclurin, that is of tinctorial value, and this substance has but feeble dyeing properties. Maclurin, however, found considerable commercial use at one time in the form of its dis-azobenzene derivative known as "Patent Fustin".</p>
<p>Besides maclurin, a number of hydroxylated derivatives of benzophenone occur in nature, but they have no tinctorial value. It has, however, been thought advisable to introduce a brief account of the two most important of these, viz. cotoïn and phloretin, in particular, in view of the attempt made by Perkin and Martin (Chem. Soc. Trans., 1897, 1149) to obtain from them products of tinctorial value similar to Patent Fustin".</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-29645435048984038132023-10-21T13:31:00.001+03:002023-10-21T13:31:17.010+03:00Drosera whittageri(CHAPTER II. The Naphthoquinone Group.) (Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p><em>Drosera whittakeri</em> is found in Australia, and grows plentifully on the hills near Adelaide. The tuber of this plant consists of an inner solid but soft nucleus full of reddish sap or juice, and an outer series of easily detached thin, and more or less dry, layers of an almost black material. Between these layers are to be found small quantities of a brilliant red colouring matter, the amount varying in tubers of different size and age, but apparently more plentiful in the older plants (Rennie, Chem. Soc. Trans., 1887, 51, 371; 1893, 63, 1083).</p>
<p>The colouring matter is extracted from the tubers by means of hot alcohol, the solution evaporated, and the residue, containing a little alcohol, is then mixed with water and allowed to stand. The product is dried, sublimed, and the brilliant vermilion powder, which contains two substances, is fractionally crystallised from boiling alcohol, or acetic acid.</p>
<p>[---]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-15604737014372818542023-10-21T11:57:00.001+03:002023-10-21T11:57:51.628+03:00Lomatiol(CHAPTER II. The Naphthoquinone Group.) (Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>This colouring matter, which is closely related to lapachol, has been obtained from the seeds of the <em>Lomatia ilicifolia</em> and <em>Lomatia longifolia</em>, which occur in Australia (N.S.W. and Victoria).</p>
<p>The colouring matter is obtained by extracting the seeds with boiling water acidified with acetic acid, and allowing the filtered extract to cool, when the product crystallises out. It is recrystallised from the same solvent.</p>
<p>[---]</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0tag:blogger.com,1999:blog-2590151079260894896.post-17950350971453480272023-08-13T17:25:00.000+03:002023-08-13T17:25:44.558+03:00Lapachol.(CHAPTER II. The Naphthoquinone Group.) (Osa artikkelista)<span style="float:right;width:35%;margin:0 0 1em 1em;font-size:85%;color:black;"><p>The Natural Organic Colouring Matters<br />
By<br />
Arthur George Perkin, F.R.S., F.R.S.E., F.I.C., professor of colour chemistry and dyeing in the University of Leeds<br />
and<br />
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<br />
Longmans, Green and Co.<br />
39 Paternoster Row, London<br />
Fourth Avenue & 30th Street, New York<br />
Bombay, Calcutta, and Madras<br />
1918</p>
<p style="color:red;">Kaikki kuvat (kemialliset kaavat) puuttuvat // None of the illustrations (of chemical formulas) included.</p></span>
<p>This colouring matter has been obtained from the wood of the Lapacho tree, from Greenheart wood, and also from Bethaberra wood. It was from the first-named that Arnaudon (Comptes rend., 1858, 46, 1154) originally obtained it by extracting the wood with alcohol, and recrystallising the product from a mixture of alcohol and ether. Stein (J. f. pr. Chem., 99, 1) showed that the same colouring matter was present in Greenheart wood, whilst Green and Hooker (Amer. Chem. Jour., 11, 267) obtained it from Bethaberra wood.</p>
<p>According to Paternò (Gazetta, 12, 337; 21, 374) the colouring matter is best extracted from the wood by means of soda solution (1 gram soda crystals in 16 grams water for 20 grams finely divided wood), the product being precipitated from the combined extracts by means of hydrochloric acid, purified by extraction with barium hydroxide solution and reprecipitation with acid. The product thus obtained when recrystallised from benzene is readily obtained in a pure condition.</p> Päivihttp://www.blogger.com/profile/16739490706796543962noreply@blogger.com0