Alizarin, synthetic

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A synthetic form of alizarin (1,2-dihydroxyanthraquinone) was first made in 1868 by Carl Graebe and Carl Lieberman, from anthracene, a coal tar product. Prior to that time, alizarin was obtained from the root of the madder plant, Rubia tinctorum L.. The orthorhombic, orange-red crystals of alizarin appear brownish-yellow in powder form. Alizarin is most commonly used for the derivatization of other dyes, but it is also known as a textile dye, a pigment, and an indicator. To prepare alizarin crimson pigment, alizarin is precipitated on a neutral base of alumina trihydrate producing a brilliant, transparent color that has fair to good permanency. Alizarin will turn blue to purple in basic aqueous solutions, but it is more often used as an acid-base indicator in alcoholic solutions (0.5%) where it changes from yellow at pH 5.5 to red at pH 6.8. Alizarin is also used in spot tests as a reagent for [aluminum|aluminum]], indium, mercury, zinc, and zirconium. As a textile dye, the cloth (cotton, wool, or silk) must be mordanted with a metal oxide. The shade produced depends on the metal present: aluminum yields a red; iron, a dark violet; and chromium, a reddish-brown.

Synonyms and Related Terms

1,2-dihydroxyanthraquinone; alizarine; Pigment Red 83 (calcium lake); Mordant Red 11; CI 58000; rouge d'alizarine (Fr.); Alizarin, synthetisch (Deut.); alizarina sintética (Esp.); alizarini, synthetiki (Gr.); alizarina sintetica (It.); alizarine (Ned.); alizarina, sintética (Port.); permanent violet; permanent crimson; alizarin crimson; crimson madder;


PR083 Alizarin, synthetic.jpg

Chemical structure

Alizarin, synthetic.jpg

Other Properties

Soluble in aromatic solvents, acetone, hot methanol and ether.

Partially soluble in ethanol and water.

Alizarin does not fluoresce in ultraviolet light. Turns blue-purple in dilute alkaline solutions.

ISO R105 Lightfastness Classification = 4-5

Composition C14H6O2(OH)2
CAS 72-48-0
Melting Point 289-290
Molecular Weight mol. wt. = 240.22
Boiling Point 430

Hazards and Safety

Combustible. Slight potential for allergic reaction by contact, inhalation or ingestion.

Mallinckrodt Baker: MSDS

Sources Checked for Data in Record

  • Artists' Pigments: A Handbook of their History and Characteristics, Elisabeth West FitzHugh, Oxford University Press, Oxford, Vol. 3, 1997 Comment: H.Schweppe, J.Winter, "Madder and Alizarin"
  • Encyclopedia Britannica, Comment: "alizarin" [Accessed May 24, 2003]. Discovered 1868, first sold 1871
  • R. J. Gettens, G.L. Stout, Painting Materials, A Short Encyclopaedia, Dover Publications, New York, 1966
  • G.S.Brady, Materials Handbook, McGraw-Hill Book Co., New York, 1971 Comment: p. 475
  • Ralph Mayer, A Dictionary of Art Terms and Techniques, Harper and Row Publishers, New York, 1969 (also 1945 printing) Comment: Discovered 1868
  • Reed Kay, The Painter's Guide To Studio Methods and Materials, Prentice-Hall, Inc., Englewood Cliffs, NJ, 1983
  • Hermann Kuhn, Conservation and Restoration of Works of Art and Antiquities, Butterworths, London, 1986 Comment: First appeared for sale in 1870
  • Michael McCann, Artist Beware, Watson-Guptill Publications, New York City, 1979
  • Monona Rossol, The Artist's Complete Health and Safety Guide, Allworth Press, New York, 1994
  • R.Feller, M.Curran, C.Bailie, 'Identification of Traditional Organic Colorants Employed in Japanese Prints and Determination of their Rates of Fading', Japanese Woodblock Prints, Allen Memorial Art Museum, Oberlin College, Oberlin, 1984 Comment: ISO rating
  • A.Scharff, 'Synthetic dyestuffs for textiles and their fastness to washing', ICOM-CC Preprints Lyon, Getty Conservation Institute, Los Angeles, 1999 Comment: A.Scharff, "Synthetic dyestuffs for textiles and their fastness to washing" in ICOM Preprints, Lyon, 1999. p.654-660.
  • Website address 1 Comment:
  • Colour Index International online at Comment: Structure; gives discoverer of calcium lake as Robequet & Colin 1826

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