Alizarin
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, 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 dye to be produced synthetically.
| Names | |
|---|---|
| Preferred IUPAC name
1,2-Dihydroxyanthracene-9,10-dione | |
| Other names
1,2-Dihydroxy-9,10-anthracenedione 1,2-Dihydroxyanthraquinone Turkey red Mordant red 11 Alizarin B Alizarin red | |
| Identifiers | |
3D model (JSmol) |
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| 3DMet | |
| 1914037 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.711 |
| 34541 | |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
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SMILES
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| Properties | |
| C14H8O4 | |
| Molar mass | 240.214 g·mol−1 |
| Appearance | orange-red crystals or powder |
| Density | 1.540 g/cm3 |
| Melting point | 289.5 °C (553.1 °F; 562.6 K) |
| Boiling point | 430 °C (806 °F; 703 K) |
| slightly to sparingly soluble | |
| Acidity (pKa) | 6.94 |
| Hazards | |
| GHS labelling: | |
| Warning | |
| H302, H315, H319 | |
| P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501 | |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related compounds |
anthraquinone, anthracene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
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 in the past.