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Copper aspirinate



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Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (August 2007)
Copper aspirinate
IUPAC name dicopper 2-acetyloxybenzoate
Other names tetrakis-μ-acetylsalicylato-dicopper(II),
copper(II) aspirinate, cupric aspirinate, cupric aspirin complex
Identifiers
CAS number 23642-01-5
PubChem 92244
SMILES CC(=O)OC1=CC=CC=C1C(=O)[O-].CC(=O)OC1=
CC=CC=C1C(=O)[O-].CC(=O)OC1=CC=CC=C1C(=O)
[O-].CC(=O)OC1=CC=CC=C1C(=O)[O-].[Cu+2].[Cu+2]
InChI InChI=1/4C9H8O4.2Cu/c4*1-6(10)13-8-5-3
-2-4-7(8)9(11)12;;/h4*2-5H,1H3,(H,11,12);
;/q;;;;2*+2/p-4/f4C9H7O4.2Cu/q4*-1;2m
Properties
Molecular formula C36H28Cu2O16
Molar mass 843.69g/mol
Appearance Bright blue crystalline solid.
Melting point

248°C (decomp.)

Related Compounds
Other cations Zinc aspirinate, Aluminium aspirinate
Related compounds Aspirin
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Copper(II) aspirinate is an aspirin chelate of copper(II) cations (Cu2+). It is used to treat rheumatoid arthritis.

Preparation

Copper aspirinate can be prepared by several methods. In one route of preparation, an excess of acetylsalicylic acid is dissolved in aqueous sodium carbonate. Sodium hydroxide is not suitable for this purpose, because it will hydrolyse acetylsalicylic acid (ASA) into salicylic acid and sodium acetate.

2 HC9H7O4 + Na2CO3 → 2 NaC9H7O4 + CO2↑ + H2O

The resulting solution is then filtered to remove any undissolved acetylsalicylic acid and is mixed with a solution containing Cu2+ cations (copper(II) sulfate is suitable), precipitating bright blue crystals of copper aspirinate immediately. The crystals can then be filtered from solution, washed, and recrystallized. An excess of acetylsalicylic acid is used in the first step, because it eliminates the possibility of unreacted carbonate anions precipitating the copper in this step.

4 NaC9H7O4 + 2 CuSO4 → C36H28Cu2O16↓ + 2 Na2SO4

Medicinal Use

Copper aspirinate has been proven effective as a treatment for rheumatoid arthritis.[1]

Other Uses

The use of copper aspirinate as a pigment in PVC and Polystyrene has also been investigated. [2]

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Copper_aspirinate". A list of authors is available in Wikipedia.
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