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|Section2= |Section7= |Section8= }} Alizarin or 1,2-dihydroxyanthraquinone (also known as Mordant Red 11 and Turkey Red〔(SigmaAldrich Catalog: Alizarin )〕) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus.〔The primary madder species from which alizarin historically has been obtained is ''Rubia tinctorum''. See also 〕 In 1869, it became the first natural pigment to be duplicated synthetically. Alizarin is the main ingredient for the manufacture of the madder lake pigments known to painters as Rose madder and Alizarin crimson. Alizarin in the most common usage of the term has a deep red color, but the term is also part of the name for several related non-red dyes, such as Alizarine Cyanine Green and Alizarine Brilliant Blue. A notable use of alizarin in modern times is as a staining agent in biological research because it stains free calcium and certain calcium compounds a red or light purple color. Alizarin continues to be used commercially as a red textile dye, but to a lesser extent than 100 years ago. ==History== Madder has been cultivated as a dyestuff since antiquity in central Asia and Egypt, where it was grown as early as 1500 BC. Cloth dyed with madder root pigment was found in the tomb of the Pharaoh Tutankhamun and in the ruins of Pompeii and ancient Corinth. In the Middle Ages, Charlemagne encouraged madder cultivation. Madder was widely used as a dye in Western Europe in the Late Medieval centuries.〔Many examples of the use of the word "madder", meaning the roots of the plant ''Rubia tinctorum'' used as a dye, are given in the (''Middle English Dictionary'' ), a dictionary of late medieval English.〕 In 17th century England, alizarin was used as a red dye for the clothing of the parliamentary New Model Army. The distinctive red color would continue to be worn for centuries (though also produced by other dyes such as cochineal), giving English and later British soldiers the nickname of "redcoats". The madder dyestuff is combined with a dye mordant. According to which mordant used, the resulting color may be anywhere from pink through purple to dark brown. In the 18th century the most valued color was a bright red known as "Turkey Red". The combination of mordants and overall technique used to obtain the Turkey Red originated in the Middle East or Turkey (hence the name). It was a complex and multi-step technique in its Middle Eastern formulation, some parts of which were unnecessary.〔 Additional 18th century history at (【引用サイトリンク】 Turkey Red Dyeing in Blackley - The Delaunay Dyeworks )〕 The process was simplified in late 18th-century Europe. By 1804, a dye maker George Field in Britain had refined a technique to make ''lake'' madder by treating it with alum, and an alkali,〔George Field's notes are held at the Courtauld Institute of Art. See (【引用サイトリンク】 FIELD, George (?1777-1854) )〕 that converts the water-soluble madder extract into a solid, insoluble pigment. This resulting ''madder lake'' has a longer-lasting color, and can be used more efficaciously, for example by blending it into a paint. Over the following years, it was found that other metal salts, including those containing iron, tin, and chromium, could be used in place of alum to give madder-based pigments of various other colors. This general method of preparing lakes has been known for centuries but was simplified in the late 18th and early 19th centuries. In 1826, the French chemist Pierre-Jean Robiquet found that madder root contained two colorants, the red alizarin and the more rapidly fading purpurin.〔See: * Pierre-Jean Robiquet and Jean-Jacques Colin (1826) ("Sur un nouveau principe immédiat des vègétaux (l’alizarin) obtenu de la garance" ) (On a new substance from plants (alizarin) obtained from madder), ''Journal de pharmacie et des sciences accessoires'', 2nd series, 12 : 407–412. * Jean-Jacques Colin and Pierre-Jean Robiquet (1827) ("Nouvelles recherches sur la matierè colorante de la garance" ) (New research into the coloring material of madder), ''Annales de chimie et de physique'', 2nd series, 34 : 225–253.〕 The alizarin component became the first natural dye to be synthetically duplicated in 1868 when the German chemists Carl Graebe and Carl Liebermann, working for BASF, found a way to produce it from anthracene.〔Note: * In 1868, Graebe and Liebermann showed that alizarin can be converted into anthracene. See: C. Graebe and C. Liebermann (1868) ("Ueber Alizarin, und Anthracen" ) (On alizarin and anthracene), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', 1 : 49-51. * In 1869, Graebe and Liebermann announced that they had succeeded in transforming anthracene into alizarin. See: C. Graebe and C. Liebermann (1869) ("Ueber künstliche Bildung von Alizarin" ) (On the artificial formation of alizarin), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', 2 : 14. * For Graebe and Liebermann's original process for making alizarin from anthracene, see: Charles Graebe and Charles Liebermann, ("Improved process of preparing alizarine," ) U.S. Patent no. 95,465 (issued: October 5, 1869). (See also their English patent, no. 3,850, issued December 18, 1868.) * A more efficient process for making alizarin from anthracene was developed by Caro, Graebe and Liebermann in 1870. See: H. Caro, C. Graebe, and C. Liebermann (1870) ("Ueber Fabrikation von künstlichem Alizarin" ) (On the manufacture of artificial alizarin), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', 3 : 359-360.〕 About the same time, the English dye chemist William Henry Perkin independently discovered the same synthesis, although the BASF group filed their patent before Perkin by only one day. The subsequent discovery (made by Broenner and Gutzhow in 1871) that anthracene could be abstracted from coal tar further advanced the importance and affordability of alizarin's artificial synthesis. The synthetic alizarin could be produced for a fraction of the cost of the natural product, and the market for madder collapsed virtually overnight. The principal synthesis entailed oxidation of anthraquinone-2-sulfonic acid with sodium nitrate in concentrated sodium hydroxide. Alizarin itself has been in turn largely replaced today by the more light-resistant quinacridone pigments developed at DuPont in 1958. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「alizarin」の詳細全文を読む スポンサード リンク
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