Alizarin Complexone Chemical Properties

Melting point:

~185 °C (dec.)

Boiling point:

511.79°C (rough estimate)

Density 

1.4951 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

2-8°C

solubility 

DMF: 10 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.125 mg/ml

pka

1.71±0.10(Predicted)

form 

Fine Powder

color 

Brown

Water Solubility 

Slightly soluble (0.2 g/L)

BRN 

2190028

Stability:

Incompatible with strong oxidizing agents.

InChI

InChI=1S/C19H15NO8/c21-13(22)7-20(8-14(23)24)6-9-5-12-15(19(28)16(9)25)18(27)11-4-2-1-3-10(11)17(12)26/h1-5,25,28H,6-8H2,(H,21,22)(H,23,24)

InChIKey

PWIGYBONXWGOQE-UHFFFAOYSA-N

SMILES

C(O)(=O)CN(CC(O)=O)CC1=C(O)C(O)=C2C(=C1)C(=O)C1=C(C=CC=C1)C2=O

CAS DataBase Reference

3952-78-1(CAS DataBase Reference)

EPA Substance Registry System

Glycine, N-(carboxymethyl)-N-[(9,10-dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenyl)methyl]- (3952-78-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

RTECS 

AH0585000

TSCA 

Yes

HS Code 

29225090

MSDS

• Language:English Provider:Alizarin Fluorine Blue
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Alizarin Complexone Usage And Synthesis

Description

Alizarin-3-methyliminodiacetic acid is a colorimetric dye for the detection of fluoride ions. It reacts with fluoride to form a lilac-blue complex which can be quantified colorimetrically at 620 nm to determine fluoride concentration. Alizarin-3-methyliminodiacetic acid has been used to visualize fluoride deposition and bone mineralization during development in medaka larvae. It is also an inhibitor of inducible nitric oxide synthase (iNOS; IC₅₀ = 35 nM).

Chemical Properties

Brown-orange crystals, insoluble in water

Uses

Alizarin Complexone is used for the determination of fluorine and other anions. ATA is also a potent inhibitor of protein-nucleic acid interactions.

Uses

Alizarin-3-methyliminodiacetic acid has been used:

• for live staining of mineralized bone matrix
• to double-label the bone for dynamic bone histomorphometry at the femoral mid-diaphysis in the rat
• as a label in histomorphometry of the tibial diaphysis to indicate new bone formation in the rat

Uses

Alizarin is the main ingredient for the manufacture of the madder lake pigments known to painters as Rose madder and Alizarin crimson. 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 Red is used in a biochemical assay to determine, quantitatively by colorimetry, the presence of calcific deposition by cells of an osteogenic lineage.

Definition

ChEBI: A dihydroxyanthraquinone compound in which the hydroxy groups are at C-1 and C-2 and which has a bis[(carboxymethyl)amino]methyl substituent at the 3-position.

General Description

Alizarin-3-methyliminodiacetic acid is used in the colorimetric detection of fluorine. It is a dye employed to stain mineralized bones of the preserved specimen from vertebrates.

Hazard

Anthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and coma;
Deaths have been reported after children ingested Rhamnus berries;
Has antiretroviral activity;
An irritant;
Harmful by ingestion, inhalation, or skin absorption;
Toxic if swallowed.

Purification Methods

It is purified by suspending it in 0.1M NaOH (1g in 50mL), filtering the solution and extracting alizarin with 5 successive portions of CH2Cl2. Then add HCl dropwise to precipitate the reagent, stirring the solution in an ice bath. Filter the precipitate onto a glass filter, wash it with cold water and dry it in a vacuum desiccator over KOH [Ingman Talanta 20 135 1973, Beilstein 14 IV 931].

Mode of action

Alizarin (1,2-dihydroxyanthraquinone) could form deeply colored metal complexes. Their stability can be increased considerably when edta-derived substituents are attached to the alizarin frame as a commercially available product of this type, alizarin complexone (AC) is a very useful reagent for the spectrophotometric determination of metals. The high stability of such metal complexes is essentially based on the chelate formation at the tridentate complexone substituent. However, if the coordination is restricted to this substituent, the spectral properties of alizarin should not be affected by metal cations owing to the electronically insulating methylene group between the complexone substituent and the alizarine nucleus. Accordingly, the color change observed upon complexation of AC is a consequence of forming an additional bond from a phenolate of the alizarin ring system to the metal[1]. Due to AC's low solubility in water, it could be soluble in ethanol in experiments. A solution of AC is yellow and displays an absorption with λmax = 430 nm(e = 5200 M^-1 cm^-1). The luminescence spectrum consists of two bands at λmax = 476 nm and 629 nm.

References

[1] Horst Kunkely, Arnd Vogler. “Fluorescence of alizarin complexone and its metal complexes.” Inorganic Chemistry Communications 10 3 (2007): Pages 355-357.

Alizarin Complexone (3952-78-1)Related Product Information

• Iminodiacetic acid
• Ethylenediaminetetraacetic acid disodium salt
• Folic acid
• Alizarin
• 1,2,5,8-TETRAHYDROXYANTHRAQUINONE
• Nitrilotriacetic acid
• Glycine
• Trypan Blue
• ACID ALIZARIN VIOLET N
• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Aminophenylacetic acid
• 1.10-Phenanthroline
• Alizarin Red S
• Protocatechualdehyde
• 2-Hydroxybenzylamine
• Catechol
• 2,4-Dimethylphenol
• 3'-Methylacetophenone