Copper aspirinate

Copper aspirinate
IUPAC name dicopper 2-acetyloxybenzoate
Other names tetrakis-μ-acetylsalicylato-dicopper(II), copper(II) aspirinate, cupric acetylsalicylate, cupric aspirinate, cupric aspirin complex
Identifiers
CAS number	23642-01-5 Y
PubChem	92244
Jmol-3D images	Image 1
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	248-255°C (decomp.)
Related compounds
Other cations	Zinc aspirinate, Aluminium aspirinate
Related compounds	Aspirin
Y aspirinate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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 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.

4 NaC₉H₇O₄ + 2 CuSO₄ → C₃₆H₂₈Cu₂O₁₆↓ + 2 Na₂SO₄

Medicinal Use

Copper aspirinate has been proven effective as a treatment for rheumatoid arthritis.^[1] The studies on animal models suggest that copper aspirinate is very promising in treating against thrombotic diseases and it has all the prospects of success in becoming an antithrombotic drug that prevents and treats thrombotic diseases in humans.^[2]

Other uses

The use of copper aspirinate as a pigment in PVC and Polystyrene has also been investigated.^[3]

External links

• IR Spectrum from Eckerd College's Chem Department

Footnotes

1. ^ "Rheumatoid Arthritis (RA)". Copper Development Association. June 2000. http://www.copper.org/innovations/2000/06/medicine-chest.html. 
2. ^ Weiping Liu,corresponding author1 Huizhou Xiong, Yikun Yang Ling Li, Zhiqiang Shen, and Zhihe Chen (1998). "Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases". Met Based Drugs. (Hindawi Publishing Corporation) 5 (3): 123–126. doi:10.1155/MBD.1998.123. PMC 2365110. PMID 18475833. http://www.copper.org/innovations/2000/06/medicine-chest.html. 
3. ^ 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:10.1016/0014-3057(91)90155-H.