Madder lake
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| Names | |
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Preferred IUPAC name
1,2-Dihydroxyanthracene-9,10-dione
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| Other names
1,2-Dihydroxy-9,10-anthracenedione
1,2-Dihydroxyanthraquinone Turkey red Mordant red 11 Alizarin B Alizarin red |
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| Identifiers | |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.711 |
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PubChem CID
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| Properties | |
| C14H8O4 | |
| Molar mass | 240.21 g·mol−1 |
| Appearance | orange-red crystals or powder |
| Density | 1.540 g/cm3 |
| Melting point | 279 to 283 °C (534 to 541 °F; 552 to 556 K) |
| Boiling point | 430 °C (806 °F; 703 K) |
| slightly to sparingly soluble | |
| Acidity (pKa) | 6.94 |
| Hazards | |
| Safety data sheet | External MSDS |
| R-phrases (outdated) | R36 R37 R38 |
| S-phrases (outdated) | S26 S36 |
| Related compounds | |
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Related compounds
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anthraquinone, anthracene |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Alizarin or 1,2-dihydroxyanthraquinone (also known as Mordant Red 11 and Turkey Red) is an organic compound with formula C
14H
8O
4 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. 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.
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. 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".
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Wikipedia