ChemicalBook > CAS DataBase List > Alizarin

Alizarin

Product Name
Alizarin
CAS No.
72-48-0
Chemical Name
Alizarin
Synonyms
Alizarin Red;SULFATED CASTOR OIL;1,2-DIHYDROXYANTHRAQUINONE;CI 58000;Alizarine;Aliazrin;Alizarine Red;TURKEY RED OIL;MORDANT RED 11;C.I. Pigment Red 83
CBNumber
CB4854164
Molecular Formula
C14H8O4
Formula Weight
240.21
MOL File
72-48-0.mol
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Alizarin Property

Melting point:
287 °C
Boiling point:
430 °C
Density 
1.06 g/mL at 20 °C
refractive index 
1.5190 (estimate)
Flash point:
430°C subl.
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Solubility Virtually insoluble in water; moderately soluble in ethanol, soluble in benzene, toluene, Ixylene, pyridine, acetic acid
form 
Fine Powder
Colour Index 
58000
pka
6.77(at 25℃)
color 
Orange to orange-brown
PH
5.5～7.2
PH Range
Yellow (5.5) to red (6.8);Red (10.1) to purple (12.1)
Water Solubility 
Soluble in hexane and chloroform. Slightly soluble in water.
λmax
567nm, 609nm
Merck 
14,251
BRN 
1914037
Stability:
Stable. Incompatible with strong oxidizing agents, strong bases.
Biological Applications
Detecting microorganisms; treating dermatological conditions
Major Application
Plasma displays, Antireflective coatings, chemical-mechanical polishing, photoreceptors, glass coatings, paints, anticorrosion coatings, thermoplastics, wood coloring, textiles, pH sensor device, detergent, hair dyes, darkening skin, cosmetics, parasiticide, antifungal agent
InChIKey
RGCKGOZRHPZPFP-UHFFFAOYSA-N
LogP
2.479 (est)
CAS DataBase Reference
72-48-0(CAS DataBase Reference)
NIST Chemistry Reference
Alizarin(72-48-0)
EPA Substance Registry System
Alizarin (72-48-0)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/38-36/37/38
Safety Statements 
26-36-24/25-22
WGK Germany 
3
RTECS 
YO8300000
TSCA 
Yes
HS Code 
29146990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
122777
Product name
Alizarin
Purity
Dye content 97%
Packaging
100g
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
122777
Product name
Alizarin
Purity
Dye content 97%
Packaging
500g
Price
$722
Updated
2024/03/01
TCI Chemical
Product number
D0242
Product name
Alizarin
Purity
>95.0%(HPLC)
Packaging
25g
Price
$33
Updated
2024/03/01
Alfa Aesar
Product number
A14404
Product name
Alizarin, 94%
Packaging
100g
Price
$55.6
Updated
2024/03/01
Alfa Aesar
Product number
A14404
Product name
Alizarin, 94%
Packaging
500g
Price
$219
Updated
2024/03/01
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Alizarin Chemical Properties,Usage,Production

Chemical Properties

orange-red crystals or powder

History

In ancient times, alizarin was the preferred red dye. Cloth dyed with it has been found in Egyptian tombs dating 6000 years ago. The dye is found in the madder plant, a member of the Rubiaceae family. In 1944 about 35 species of this plant were known, but the use of more sophisticated analytical methods led to the detection of many more species; by 1984 the number had increased to 50. Alizarin is a mordant dye forming various colored coordination complexes with different metallic salts.

Uses

antimutagen

Uses

Alizarin has a major application in the manufacture of the madder lake pigments which is commonly called as Rose madder and Alizarin crimson. It is involved in the studies of bone growth, osteoporosis, bone marrow and calcium deposits in the vascular system. It is also used as a stain in calcite and aragonite to identify calcium carbonate, and synovial fluid to asses for basic calcium phosphate crystals. It is used in colorimetric measurements for quantification of amine extraction by model food simulants from epoxy polymer.

Uses

Alizarin is used widely as a prominent red dye for textile facbrics. Alizarin red is now used in biochemical assay to determine quantitatively by colorimetry, the presence of calcific deposition by ce lls of the osteogenic lineage. Alzarine derivatives was evaluated as new inhibitors of the HIV-1 reverse transcriptase associated DNA polymerase and RNase H. Alizarin was also shown to inhibit prolife ration, tumor growth and suppress tumorigenesis in human osteosarcoma and breast cancer cell representative for bone metastasis.

Definition

ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione in which the two hydroxy groups are located at positions 1 and 2.

Preparation

(a) 2 – Bromoanthraquinone and Potassium hydroxide heating; (b) 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid (Sodium) and Sodium hydroxide and Sodium nitrate and Sodium chlorate heating; (C) Anthracene-9,10-dione?and Sodium hydroxide and Sodium chlorate and Sodium nitrate heating (GP 186526); (d) in the presence of Sodium nitrite and Sodium hydroxide and Anthracene-9,10-dione?and Sodium nitrate heating (GP 241806245 987); (e) in the Oxidant and Sodium sulfite and the presence of lime, anthracene in a nitrocellulose derivatives and Sodium hydroxide heating (GP 292247); (f) 2 – Anthraquinonesulfonic acid in the presence of air, with the Sodium hydroxide Etanol wetting treatment (GP 287270); (g) 2-Chloroanthracene-9,10-dione Sodium chlorate in the presence of alkali fusion for (USP 1744815); (h) 2-Methylanthracene-9,10-dione in the presence of Oxidant, with Sodium hydroxide treatment (BP 293328).

Definition

An important orange-red organic compound used in the dyestuffs industry to produce red lakes. It occurs naturally in the root of the plant madder and may also be synthesized from anthraquinone.

Definition

alizarin: An orange-red compound,C14H8O4. The compound is a derivativeof anthraquinone, with hydroxylgroups substituted at the 1and 2 positions. It is an importantdyestuff producing red or violetlakes with metal hydroxide.Alizarin occurs naturally as the glucosidein madder. It can be synthesizedby heating anthraquinone withsodium hydroxide.

Biological Activity

alizarin is an anthraquinone dye for detecting the presence of calcium salts [1].alizarin belongs to the anthraquinone group. it is a chelator for calcium and is commonly used to stain the calcifying or calcio-receptive zone of the collagenous matrix where calcium salts are being deposited. on the other hand, the alizarin complexone is used for bone staining in vivo to study bone remodeling [1].alizarin is proved to have anti-tumor efficacy. it suppresses the cell growth of the prostate cancer, breast cancer and osteosarcoma cell lines in vitro. among these, the osteosarcoma cells appear to be most sensitive. the ic50 values of alizarin against three osteosarcoma cell lines saos-2, mg-63 and u-2 os are 27.5, 29 and 69.9μg/ml, respectively. alizarin inhibits the cell growth through cell proliferation blockade rather than induction of apoptosis. it inhibits the phosphorylation of erk. in addition, alizarin is also found to induce s-phase arrest as well as a decrease of the g0/g1 and g2/m phases [1].

Synthesis

1,2-Dihydroxyanthraquinone is prepared from anthraquinone by alkali melt or from anthraquinone-2-sulfonic acid with 50 % aqueous sodium hydroxide and sodium nitrate at 190 – 200 ?C .

Properties and Applications

commonly known as 1,2-Dihydroxyanthracene-9,10-dione , calcium, aluminum mordanting for red to blue light red, chromium for dark blue light red, iron as dark purplish red. Claybank powder. Slightly soluble in water, but soluble in Methanol, Acetone Etanol, boiling, alkali and Cellosolve, slightly soluble in benzene, Carbon tetrachloride, insoluble in cold Etanol, Stout solvent, soluble in alkali liquor for royal purple. In concentrated sulfuric acid for yellow red, red yellow after diluted produce precipitation; In the Sodium hydroxide to purple. Used for wool fabric dyeing and used as organic pigment.

Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water
Alkali Acid
ISO 3-4 7 3-4 1 3 4 4
AATCC Dry 2,wet 5 7 2-3 4 4 5

Purification Methods

Alizarin crystallises from glacial acetic acid or 95% EtOH. It can also be sublimed at 110o/2mm. It is an indicator with max at 452nm (pH 5.8) and 520nm (pH 7.2). [Beilstein 8 IV 3256.]

References

[1] fotia c, avnet s, granchi d, baldini n. the natural compound alizarin as an osteotropic drug for the treatment of bone tumors. j orthop res. 2012 sep;30(9):1486-92.

Alizarin Preparation Products And Raw materials

Raw materials

Sodium anthraquinone-2-sulfonate 2-Anthraquinonesulfonic acid Anthraquinone Potassium chlorate Sodium hydroxide Potassium nitrate

Preparation Products

Alizarin Complexone
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View Lastest Price from Alizarin manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
Alizarin 72-48-0
Price
US $45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 tons
Release date
2024-12-05
Shanghai Standard Technology Co., Ltd.
Product
Alizarin 72-48-0
Price
US $0.00/mg
Min. Order
100mg
Purity
≥98%(HPLC)
Supply Ability
100 g
Release date
2020-05-27
Zhuozhou Wenxi import and Export Co., Ltd
Product
Alizarin 72-48-0
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11

72-48-0, AlizarinRelated Search:

Alizarin Alizarin Complexone Carmine CARMINE 1,2,5,8-TETRAHYDROXYANTHRAQUINONE ANTHRACENE BROWN Alizarin Red S PURPURIN ANTHRAPURPURIN Carminic Acid ALIZARIN BLUE S 1,4-Dihydroxyanthraquinone-2-sulfonic acid 1,8-Dihydroxyanthraquinone 1,4-dihydroxy-9,10-anthracenedione CASTOR OIL, SULFONATED 1,5-Dihydroxy-9,10-anthracenedione 1,8-Diamino-4,5-dihydroxy-9,10-anthracenedion Solvent Green 28

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