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Alizarin
Alizarin
Sample of alizarin
IUPAC name
Other names 1,2-Dihydroxyanthraquinone, Turkey red, Mordant red 11, Alizarin B, Alizarin red
Identifiers
CAS number 72-48-0 Yes check.svgY
PubChem 6293
SMILES
InChI
InChI key RGCKGOZRHPZPFP-UHFFFAOYAG
ChemSpider ID 6056
Properties
Molecular formula C14H8O4
Molar mass 240.21 g mol−1
Appearance orange-red crystals or powder
Melting point

279–83 °C

Boiling point

430 °C

Hazards
MSDS External MSDS
R-phrases R36 R37 R38
S-phrases S26 S36
Related compounds
Related compounds anthraquinone, anthracene
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Alizarin is an organic compound that is historically important as a prominent dye. It is an anthraquinone originally derived from the root of the madder plant. In 1869, it became the first natural pigment to be duplicated synthetically.[1] Alizarin is also the name for a variety of related dyes, such as "Alizarine Cyanine Green G" and "Alizarine Brilliant Blue R." Can also be used to identify the color "Alizarin Crimson". The word alizarin derives from the Arabic al-usara, juice.[2]

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".

Contents

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.

alizarin color

By 1804, the English dye maker George Field[3] had refined the technique to lake madder by treating it with alum, and an alkali,[4] 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.[5]

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.

Applications – Alizarin Red

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.

In clinical practice it is also used to stain synovial fluid to assess for basic calcium phosphate crystals.

Alizarin Crimson

Alizarin Crimson
About these coordinates About these coordinates
— Color coordinates —
Hex triplet #E32636
RGBB (r, g, b) (227, 38, 54)
CMYKH (c, m, y, k) (0, 85, 70, 1)
HSV (h, s, v) (355°, 83%, 89%)
Source [Unsourced]
B: Normalized to [0–255] (byte)
H: Normalized to [0–100] (hundred)

Alizarin Crimson can also be identified as "Alizarin". At right is displayed the color alizarin crimson.

Alizarin crimson in human culture

Music

  • Alizarin crimson is mentioned in Karlheinz Stockhausen's 1966/67 musical composition Hymnen, where it is included in a spoken fugue where the names of dozens of different shades of red are intermingled as a symbol of the various forms of Communism that existed at that time.

See also

References

  1. ^ 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.
  2. ^ alizarin. Dictionary.com. Dictionary.com Unabridged (v 1.1). Random House, Inc. http://dictionary.reference.com/browse/alizarin (accessed: January 02, 2007).
  3. ^ 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)
  4. ^ 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.
  5. ^ Daniel V. Thompson – The Materials and Techniques of Medieval Painting – Dover – pp115–124. ISBN 0-486-20327-1


External links

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1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

ALIZARIN, or I. 2 < [[Dioxyanthraquinone, 6h4 Co? C6h2(Oh)2[I.2], C]] a vegetable dyestuff formerly prepared from madder root (Rubia tinctorum) which contains a glucoside ruberythric acid (C26H28014). This glucoside is readily hydrolysed by acids or ferments,breaking up into alizarin and glucose: 214 O Ruberythric acid = Glucose+Alizarin.

Alizarin was known to the ancients, and until 1868 was obtained entirely from madder root. The first step in the synthetical production of alizarin was the discovery in 1868 of C. Graebe and C. Liebermann that on heating with zinc dust, alizarin was converted into anthracene. In order to synthesize alizarin, they converted anthracene into anthraquinone and then brominated the quinone. The dibrominated product so obtained was then fused with caustic potash, the melt dissolved in water, and on the addition of hydrochloric acid to the solution, alizarin was precipitated. This process, owing to its expensive nature, was not in use very long, being superseded by another, discovered simultaneously by the above-named chemists and by Sir W. H. Perkin; the method being to sulphonate anthraquinone, and then to convert the sulphonic acid into its sodium salt and fuse this with caustic soda.

In practice, the crude anthracene is purified by solution in the higher pyridine bases, after which treatment it is frequently sublimed. It is then oxidized to anthraquinone by means of sodium dichromate and sulphuric acid in leaden vats, steam heated so that the mixture can be brought to the boil. When oxidation is complete the crude anthraquinone is separated in filter presses and heated with an excess of commercial oil of vitriol to 120° C., the various impurities present in the crude material being sulphonated and rendered soluble in water, whilst the anthraquinone is unaffected; it is then washed, to remove impurities, and dried. The anthraquinone so obtained is then heated for some hours at about 150-160° C. with fuming sulphuric acid (containing about 40-50% SO 3), and by this treatment is converted into anthraquinone-O-monosulphonic acid. The solution is poured into water and sodium carbonate is added to neutralize the excess of acid, when the sodium salt of the monosulphonic acid (known as silver salt) separates out. This is filtered, washed, and then fused with caustic soda, when the sulpho-group is replaced by a hydroxyl group, and a second hydroxyl group is simultaneously formed; in order to render the formation of this second group easier, a little potassium chlorate or sodium nitrate is added to the reaction mixture. The melt is dissolved in water and the dyestuff is liberated from the sodium salt by hydrochloric or sulphuric acid, or is converted into the calcium salt by digestion with hot milk of lime, then filtered and the calcium salt decomposed by acid. The precipitated alizarin is then well washed and made into a paste with water, in which form it is put on to the market.

K. Lagodzinski (Berichte, 1895, 28, p. 1427) has synthesized alizarin by condensing hemipinic acid [(CH30)2C6H2(COOH)2] with benzene in the presence of aluminium chloride. The product on acidification gives a compound C15H1205 � H20 which is probably an oxy-methoxy-benzoyl benzoic acid. This is dissolved in cold concentrated sulphuric acid, in which it forms a yellowish red solution, but on heating to ioo° C. the colour changes to red and violet, and on pouring out upon ice, the monomethyl ether of alizarin is precipitated. This compound is hydrolysed by hydriodic acid and alizarin is obtained. It I. 43 is produced, and this on heating /CO"/N02 with sulphuric acid and glycerin is converted into alizarin blue. The trioxyanthraquinones - purpurin, anthrapurpurin, anthragallol and flavopurpurin - are also very valuable dyestuffs. These compounds may be represented by the following formulae: OH OH OH OH / / CO /OH HO/ / CO /OH / / CO /OH /CO/OH CO/?/ Unco/L) Ho?Co?% ?% `Co/%Oh. Oh Purpurin. Anthrapurpurin. Fiavopurpurin. Anthragallol.

Purpurin (1.2. 4 trioxyanthraquinone) is found with alizarin in madder root; it is now prepared synthetically by oxidizing alizarin with manganese dioxide and sulphuric acid. After the separation of the silver salt (see above) obtained on sulphonating anthraquinone, the remaining acid liquid gives on treatment with calcium carbonate the calcium salt of anthraquinone 2.6 disulphonic acid (anthraquinone-a-disulphonic acid). This is converted into the sodium salt by means of sodium carbonate, and on alkali fusion yields flavopurpurin. In a similar manner anthrapurpurin is prepared by alkali fusion of anthraquinone 2.8 disulphonic acid. Anthragallol is synthetically prepared by the condensation of benAoic and gallic acids with sulphuric acid OH i [[Cooh + I 10h - 2h20+ Hooc /Oh]] or from pyrogallol and phthalic anhydride in the presence of sulphuric acid or zinc chloride.

A. Baeyer in 1890, by heating alizarin with fuming sulphuric acid for 24-48 hours at 35-40° C., obtained a product, which after treatment with caustic soda gave a sulphuric acid ester of quinalizarin, and this after acidification and boiling was converted into quinalizarin (Alizarin Bordeaux) or 1.2.6.9 tetra-oxyanthraquinone. Penta-oxyanthraquinones have been obtained from purpurin and anthrapurpurin, while a hexaoxyanthraquinone has been obtained from 1.5 dinitro anthraquinone.


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