Copper aspirinate
From Wikipedia, the free encyclopedia
| Copper aspirinate | |
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4.png/200px-Cu2(asp)4.png) |
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-aspirinate-3D-balls.png/200px-Copper(II)-aspirinate-3D-balls.png) |
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| 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 | |
| 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 | 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 |
248-255°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 |
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Copper(II) aspirinate is an aspirin chelate of copper(II) cations (Cu2+). It is used to treat rheumatoid arthritis.
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[edit] 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.
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- 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 dried. 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.
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- 4 NaC9H7O4 + 2 CuSO4 → C36H28Cu2O16↓ + 2 Na2SO4
[edit] Medicinal Use
Copper aspirinate has been proven effective as a treatment for rheumatoid arthritis.[1]
[edit] Other Uses
The use of copper aspirinate as a pigment in PVC and Polystyrene has also been investigated. [2]
[edit] External links
[edit] Footnotes
- ^ Rheumatoid Arthritis (RA). Copper Development Association (June 2000).
- ^ Allan, J R; A Renton, W E Smith, D L Gerrard, J Birnie (1991). "A Study of the Performance of Bis(acetylsalicylate) Copper(II) and the Cobalt(II), Nickel(II) and Copper(II) Complexes of Pyridine-3,4-dicarboxylic Acid as Colouring Materials for Poly(vinyl chloride) and Polystyrene". Eur. Polym. J. 27 (7): 669–672. doi:.
