Copper aspirinate

Copper aspirinate
Names
	IUPAC name dicopper;tetrakis(2-acetyloxybenzoate)
	Other names Copper, tetrakis[mu-[2-(acetyloxy)benzoato-kappaO:kappaO']]di-; tetrakis-μ-acetylsalicylato-dicopper(II); copper(II) aspirinate; cupric acetylsalicylate; cupric aspirinate; cupric aspirin complex;
Identifiers
CAS Number	23642-01-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	83280 ;
ECHA InfoCard	100.041.622
PubChem CID	92244;
CompTox Dashboard (EPA)	DTXSID4066919 ;
	InChI InChI=1S/4C9H8O4.2Cu/c41-6(10)13-8-5-3-2-4-7(8)9(11)12;;/h42-5H,1H3,(H,11,12);;/q;;;;2+2/p-4 Key: BXBJCCCIFADZBU-UHFFFAOYSA-J ; InChI=1/4C9H8O4.2Cu/c41-6(10)13-8-5-3-2-4-7(8)9(11)12;;/h42-5H,1H3,(H,11,12);;/q;;;;2+2/p-4 Key: BXBJCCCIFADZBU-XBHQNQODAY;
	SMILES CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].[Cu+2].[Cu+2]; CC(=O)Oc0ccccc0[C-](O[Cu+2]123)O[Cu+2](O[C-](O1)c0ccccc0OC(=O)C)(O[C-](O2)c0ccccc0OC(=O)C)O[C-](O3)c0ccccc0OC(=O)C;
Properties
Chemical formula	Cu2C36H28O16
Molar mass	843.696 g·mol−1
Appearance	bright blue solid
Melting point	255 °C (491 °F; 528 K) (decomposes)
Structure
Crystal structure	monoclinic
Space group	P21/c
Lattice constant	a = 8.208, b = 10.39, c = 21.56 α = 90°, β = 104.74°, γ = 90°
Formula units (Z)	4 units per cell
Pharmacology
	Pharmacokinetics:
Biological half-life	8.67 h (Human)
Hazards
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 1 mg/m3 (as Cu)
REL (Recommended)	TWA 1 mg/m3 (as Cu)
IDLH (Immediate danger)	TWA 100 mg/m3 (as Cu)
Related compounds
Other anions	Copper benzoate; Copper salicylate;
Related compounds	Aspirin
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Copper(II) aspirinate is an aspirin chelate of copper(II) cations (Cu²⁺). It is a bright blue solid, forming monoclinic crystals.

Preparation

Copper aspirinate can be prepared treating a solution of aspirin and potassium bicarbonate with copper(II) sulfate solution.^[1]

Heating an equimolar mixture of aspirin and copper salicylate tetrahydrate in 50% aqueous ethanol results in dark blue crystals.^[4]

Research

Copper aspirinate has been investigated for its claimed anti-inflammatory,^[5]^[6] antioxidative,^[1] and antithrombotic^[7] properties as well as a potential treatment for skin disorders.^[8]

The use of copper aspirinate as a pigment in PVC and polystyrene has also been investigated.^[9]

External links

IR Spectrum from Eckerd College's Chem Department

Footnotes

^ ^a ^b ^c Fujimori, T.; Yamada, S.; Yasui, H.; Sakurai, H.; In, Y.; Ishida, T. (2005-12-01). "Orally active antioxidative copper(II) aspirinate: synthesis, structure characterization, superoxide scavenging activity, and in vitro and in vivo antioxidative evaluations". JBIC Journal of Biological Inorganic Chemistry. 10 (8): 831–841. doi:10.1007/s00775-005-0031-3. ISSN 1432-1327.
^ Manojlović-Muir, L. (1973-10-15). "The crystal structure of copper(II) aspirinate". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 29 (10): 2033–2037. doi:10.1107/S0567740873006060. ISSN 0567-7408.
^ NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).
^ Manojlović-Muir, Ljubica (1967-01-01). "Copper(II) aspirinate". Chemical Communications (London) (20): 1057b–1058. doi:10.1039/C1967001057B. ISSN 0009-241X.
^ Zhiqiang, S.; Lei, W. Y.; Li, L.; Chen, Z. H.; Liu, W. P. (1998-12-01). "Coordination of copper with aspirin improves its anti-inflammatory activity". InflammoPharmacology. 6 (4): 357–362. doi:10.1007/s10787-998-0018-0. ISSN 1568-5608.
^ Iqbal, Mohammad S.; Sher, Muhammad; Pervez, Humayun; Saeed, Maryiam (September 2008). "Pharmacokinetic Study of Copper (II) Acetylsalicylate". Biological Trace Element Research. 124 (3): 283–288. Bibcode:2008BTER..124..283I. doi:10.1007/s12011-008-8146-3. PMID 18478192.
^ Liu, Weiping; Xiong, Huizhou; Yang Ling Li, Yikun; Shen, Zhiqiang; Chen, Zhihe (1998). "Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases". Metal-Based Drugs. 5 (3): 123–126. doi:10.1155/MBD.1998.123. PMC 2365110. PMID 18475833.
^ Duncan, Clare; White, Anthony R. (2012). "Copper complexes as therapeutic agents". Metallomics. 4 (2): 134–135. doi:10.1039/C2MT00174H. ISSN 1756-5901.
^ Allan, JR; Renton, A; Smith, WE; Gerrard, DL; Birnie, J (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. Bibcode:1991EurPJ..27..669A. doi:10.1016/0014-3057(91)90155-H.

[Fujimori-1] Fujimori, T.; Yamada, S.; Yasui, H.; Sakurai, H.; In, Y.; Ishida, T. (2005-12-01). "Orally active antioxidative copper(II) aspirinate: synthesis, structure characterization, superoxide scavenging activity, and in vitro and in vivo antioxidative evaluations". JBIC Journal of Biological Inorganic Chemistry. 10 (8): 831–841. doi:10.1007/s00775-005-0031-3. ISSN 1432-1327.

[2] Manojlović-Muir, L. (1973-10-15). "The crystal structure of copper(II) aspirinate". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 29 (10): 2033–2037. doi:10.1107/S0567740873006060. ISSN 0567-7408.

[3] NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).

[4] Manojlović-Muir, Ljubica (1967-01-01). "Copper(II) aspirinate". Chemical Communications (London) (20): 1057b–1058. doi:10.1039/C1967001057B. ISSN 0009-241X.

[5] Zhiqiang, S.; Lei, W. Y.; Li, L.; Chen, Z. H.; Liu, W. P. (1998-12-01). "Coordination of copper with aspirin improves its anti-inflammatory activity". InflammoPharmacology. 6 (4): 357–362. doi:10.1007/s10787-998-0018-0. ISSN 1568-5608.

[6] Iqbal, Mohammad S.; Sher, Muhammad; Pervez, Humayun; Saeed, Maryiam (September 2008). "Pharmacokinetic Study of Copper (II) Acetylsalicylate". Biological Trace Element Research. 124 (3): 283–288. Bibcode:2008BTER..124..283I. doi:10.1007/s12011-008-8146-3. PMID 18478192.

[7] Liu, Weiping; Xiong, Huizhou; Yang Ling Li, Yikun; Shen, Zhiqiang; Chen, Zhihe (1998). "Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases". Metal-Based Drugs. 5 (3): 123–126. doi:10.1155/MBD.1998.123. PMC 2365110. PMID 18475833.

[8] Duncan, Clare; White, Anthony R. (2012). "Copper complexes as therapeutic agents". Metallomics. 4 (2): 134–135. doi:10.1039/C2MT00174H. ISSN 1756-5901.

[9] Allan, JR; Renton, A; Smith, WE; Gerrard, DL; Birnie, J (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. Bibcode:1991EurPJ..27..669A. doi:10.1016/0014-3057(91)90155-H.

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