File:Alizarin_sublimed_crop.jpg · Wikimedia Commons · See Wikimedia Commons
alizarin
Sign in to saveAlso known as Turkey Red, Alizarin Red, Alizarin B, 1,2-Anthraquinonediol, Az, Mordant Red 11, pigment red 83, C.I. 58000
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula 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. In 1869, it became the first natural dye to be produced synthetically.
Chemical data
- Formula
- C14H8O4
- Molecular weight
- 240.21 g/mol
- IUPAC name
- 1,2-dihydroxyanthracene-9,10-dione
- SMILES
- C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
- InChIKey
- RGCKGOZRHPZPFP-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 74.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 240.042
- Image
- Alizarin-sample.jpg
Show 5 more facts
- chemical formula
- C₁₄H₈O₄
- Commons category
- Alizarin
- boiling point
- 430
- canonical SMILES
- C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
- melting point
- 288
via Wikidata · CC0
~8 min read
Article
8 sectionsContents
- History
- Age of synthetic alizarin
- Structure and properties
- Applications
- See also
- References
- Further reading
- External links
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula 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. In 1869, it became the first natural dye to be produced synthetically.
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.