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Alizarin information


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
CAS Number
  • 72-48-0 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00298
Beilstein Reference
1914037
ChEBI
  • CHEBI:16866 checkY
ChEMBL
  • ChEMBL55814 checkY
ChemSpider
  • 6056 checkY
ECHA InfoCard 100.000.711 Edit this at Wikidata
Gmelin Reference
34541
KEGG
  • C01474 checkY
PubChem CID
  • 6293
UNII
  • 60MEW57T9G checkY
CompTox Dashboard (EPA)
  • DTXSID5045960 Edit this at Wikidata
InChI
  • 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
SMILES
  • O=C2c1ccccc1C(=O)c3c2ccc(O)c3O
Properties
Chemical formula
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)
Solubility in water
slightly to sparingly soluble
Acidity (pKa) 6.94
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H302, H315, H319
Precautionary statements
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 ?)
Infobox references

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 prominent 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 notable 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).

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Alizarin

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Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula C 14H 8O 4 that has...

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Alizarin Red S

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Alizarin Red S (also known as C.I. Mordant Red 3, Alizarin Carmine, and C.I 58005.) is a water-soluble sodium salt of Alizarin sulfonic acid with a chemical...

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Alizarine Yellow R

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 3–10. ISBN 9780849304880. OCLC 1024315229. "Safety Datasheet (MSDS) for alizarin yellow R". Department of Chemistry, University of Oxford. 2005. Archived...

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List of dyes

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61968-79-1 Alizarin Turkey red Mordant red 11 Pigment red 83 58000 anthraquinone 72-48-0 Alizarin blue 67410 anthraquinone 66675-89-6 Alizarin cyanin BBS...

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Rose madder

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madder plant Rubia tinctorum. Madder lake contains two organic red dyes: alizarin and purpurin. As a paint, it has been described as a fugitive, transparent...

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Diaphonization

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trypsin, and then stains the bones and cartilage with various dyes, usually alizarin red and alcian blue. Diaphonization was first developed by O. Schultze...

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Red pigments

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the early European textile industry. Alizarin pigment "A Lady and Two Gentlemen"" by Johannes Vermeer used Alizarin crimson for dramatic effect Chinese...

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Synthetic colorant

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sulfurous acids facilitated further experiments, leading to the isolation of alizarin and purpurin in 1826. Madder based pigments such as Brown Madder (obtained...

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Crimson

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pigment is also called cochineal after the insect from which it is made. Alizarin (PR83) is a pigment that was first synthesized in 1868 by the German chemists...

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Alizarin crimson

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Alizarin crimson may refer to: Alizarin crimson (color), a particular shade of red Alizarin, a paint pigment Rose madder This disambiguation page lists...

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Rubia tinctorum

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contained 40–50 times the amount of alizarin of the roots.[citation needed] The chemical name for the pigment is alizarin, of the anthraquinone-group, and...

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Anthracene

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component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm...

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Titration

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pH of 8.4, then the phenolphthalein indicator would be used instead of Alizarin Yellow because phenolphthalein would reduce the indicator error. Common...

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Carl Graebe

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He is known for the first synthesis of the economically important dye, alizarin, with Liebermann, and for contributing to the fundamental nomenclature...

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Anthraquinone dyes

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anthraquinone dyes of herbal origin is alizarin, which is extracted from the dyer's madder (Rubia tinctorum). Alizarin is the eponym for a number of structurally...

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Alizarine ink

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by Professor Christian August Leonhardi of Dresden, Germany, by adding alizarin dye (derived from the root of the madder plant) to conventional iron gall...

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Rubia

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meaning "red". The plant's roots contain an anthracene compound called alizarin that gives its red colour to a textile dye known as Rose madder. It was...

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Aluminium triacetate

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cattle. Aluminium triacetate is used as a mordant agent with dyes like alizarin, both alone and in combination. Together with aluminium diacetate or with...

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Cochineal

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depicted in the Codex Osuna (1565). After synthetic pigments and dyes such as alizarin were invented in the late 19th century, use of natural-dye products gradually...

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Calico

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cream or unbleached cotton, with a design block-printed using a single alizarin dye fixed with two mordants, giving a red and black pattern. Polychromatic...

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Hue

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of the original. Replacements are often used for chromium, cadmium and alizarin. Dominant wavelength (or sometimes equivalent wavelength) is a physical...

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Cadmium

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samples by using a minicolumn of sisal fiber (Agave sisalana) loaded with Alizarin fluorine blue by FAAS". Talanta. 89 (1): 276–279. doi:10.1016/j.talanta...

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Strawberry Thief

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pattern was the first design using the technique in which red (in this case alizarin dye) and yellow (weld) were added to the basic blue and white ground. Discharge...

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Red

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the most common red dye used from ancient times until the 19th century. Alizarin was the first synthetic red dye, created by German chemists in 1868. It...

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Pigment

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Zinc pigments: zinc white, zinc ferrite, zinc yellow Biological origins: alizarin, gamboge, cochineal red, rose madder, indigo, Indian yellow, Tyrian purple...

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Bayer

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moved to the village Wiesdorf at Rhein and settled in the area of the alizarin producer Leverkus and Sons. A new city, Leverkusen, was founded there in...

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