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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey. |
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| InChIKey = RGCKGOZRHPZPFP-UHFFFAOYAG |
| InChIKey = RGCKGOZRHPZPFP-UHFFFAOYAG |
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| PubChem = 6293 |
| PubChem = 6293 |
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| StdInChI = 1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H |
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| StdInChIKey = RGCKGOZRHPZPFP-UHFFFAOYSA-N |
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| CASNo = 72-48-0 |
| CASNo = 72-48-0 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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Revision as of 13:29, 29 November 2010
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| Names | |
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| IUPAC name
1,2-dihydroxy-9,10-anthracenedione
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| Other names
1,2-Dihydroxyanthraquinone, Turkey red, Mordant red 11, Alizarin B, Alizarin red
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.000.711 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H8O4 | |
| Molar mass | 240.214 g·mol−1 |
| Appearance | orange-red crystals or powder |
| Melting point | 279–83 °C |
| Boiling point | 430 °C |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Alizarin or 1,2-dihydroxyanthraquinone is an organic compound with formula C
14H
8O
4 that is historically important as a prominent dye, originally derived from the roots of plants of the madder genus.
Alizarin was used as a red dye for the English parliamentary "new model" army. The distinctive red color would continue to be worn for centuries, giving English and later British soldiers the nickname of "redcoat". In 1869, it became the first natural pigment to be duplicated synthetically.[1]
Different dyes were used by the British, at different times, as one dye name that is commonly cited is "cochineal". Cochineal is derived from several related species of scale insect, endemic to South America.
Alizarin is the main ingredient for the manufacture of the madder lake pigments known to painters as Rose madder and Alizarin crimson. The term is also part of the name for a variety of related dyes, such as Alizarine Cyanine Green G and Alizarine Brilliant Blue R, and gave its name to alizarin crimson, a particular shade of red. The word derives from the Arabic al-usara "juice".[2]
Occurrence
Alizarin occurs in the root of the common madder (Rubia tinctorum) and in various parts of Indian madder (Rubia cordifolia).[3]
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. It grew well in the sandy soils of the Netherlands and became an important part of the local economy.
By 1804, the English dye maker George Field[4] had refined the technique to lake madder by treating it with alum, and an alkali,[5] 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.[6]
In 1826, the French chemist Pierre-Jean Robiquet found that madder root contained two colorants, the red alizarin and the more rapidly fading purpurin. 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. 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 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.
Structure and properties
Alizarin is one of ten dihydroxyanthraquinone isomers. Its molecule can be viewed as deriving from anthraquinone by replacement of two neighboring hydrogen atoms (H) by hydroxyl groups (-OH).
It is soluble in hexane and chloroform, and can be obtained from the latter as red-purple crystals, m.p. 277–278 °C. [3]
Applications
Alizarin Red is used in a biochemical assay to determine, quantitatively by colorimetry, the presence of calcific deposition by cells of an osteogenic lineage. As such it is an early stage marker (days 10–16 of in vitro culture) of matrix mineralisation, a crucial step towards the formation of calcified extracellular matrix associated with true bone.[citation needed]
In clinical practice, it is also used to stain synovial fluid to assess for basic calcium phosphate crystals.[7]
In geology, it is used as a stain to indicate the calcium carbonate minerals, calcite and aragonite.[8].
See also
- Alizarine ink
- Aniline
- 1,2,4-Trihydroxyanthraquinone or purpurin, another red dye that occurs in madder root.
- Hydroxyanthraquinone
- Dihydroxyanthraquinone
- List of dyes
- List of colors (compact)
References
- ^ Hans-Samuel Bien, Josef Stawitz, Klaus Wunderlich “Anthraquinone Dyes and Intermediates” in Ullmann’s Encyclopedia of Industrial Chemistry 2005 Wiley-VCH, Weinheim: 2005. doi:10.1002/14356007.a02 355.
- ^ alizarin. Dictionary.com. Dictionary.com Unabridged (v 1.1). Random House, Inc. http://dictionary.reference.com/browse/alizarin (accessed: January 02, 2007).
- ^ a b Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn. using biomordant. Dyes and Pigments, Volume 76, Issue 1, , Pages 207-212. doi:10.1016/j.dyepig.2006.08.023
- ^ Field's notes are held at the Courtauld Institute of Art. See: http://www.aim25.ac.uk/cgi-bin/search2?coll_id=4107&inst_id=2 (accessed: 2007/09/05)
- ^ Winsor Newton's madder pigment is made according to his process. See http://www.winsornewton.com/artnews/EN/artnewsletterA4_english03_2002.pdf page 6. (accessed: 2007/09/03). Note that Henry Charles Newton, founder of Winsor Newton, was his assistant and friend.
- ^ Daniel V. Thompson – The Materials and Techniques of Medieval Painting – Dover – pp115–124. ISBN 0-486-20327-1
- ^ Paul H. "Alizarin red S staining as a screening test to detect calcium compounds in synovial fluid". Arthritis and rheumatism. 26 (2): 191–200. PMID 6186260.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ Green, Owen R. (2001). A manual of practical laboratory and field techniques in palaeobiology. Springer. p. 56. ISBN 9780412589805.