Alizarin

Alizarin
Ball-and-stick model of alizarin
Names
Preferred IUPAC name
1,2-Dihydroxyanthracene-9,10-dione
Other names
1,2-Dihydroxy-9,10-anthracenedione[1]
1,2-Dihydroxyanthraquinone
Turkey red
Mordant red 11
Alizarin B
Alizarin red
Identifiers
3D model (JSmol)
3DMet
1914037
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.711 Edit this at Wikidata
34541
KEGG
UNII
  • InChI=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 checkY
    Key: RGCKGOZRHPZPFP-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: RGCKGOZRHPZPFP-UHFFFAOYAG
  • O=C2c1ccccc1C(=O)c3c2ccc(O)c3O
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)[1]
Boiling point 430 °C (806 °F; 703 K)
slightly to sparingly soluble
Acidity (pKa) 6.94
Hazards
GHS labelling:
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)

Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red[2]) is an organic compound with formula C
14
H
8
O
4
that has been used throughout history as a red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus.[3] In 1869, it became the first natural dye to be produced synthetically.[4]

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 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.

  1. ^ a b Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.10. ISBN 9781498754293.
  2. ^ SigmaAldrich Catalog: Alizarin
  3. ^ The primary madder species from which alizarin historically has been obtained is Rubia tinctorum. See also Vankar, P. S.; Shanker, R.; Mahanta, D.; Tiwari, S. C. (2008). "Ecofriendly Sonicator Dyeing of Cotton with Rubia cordifolia Linn. Using Biomordant". Dyes and Pigments. 76 (1): 207–212. doi:10.1016/j.dyepig.2006.08.023.
  4. ^ Cite error: The named reference Ull was invoked but never defined (see the help page).