5-Aminosalicylic acid (CAS 89-57-6)

Usage :

For long term storage, we suggest that 5-aminosalicylic acid (5-ASA) be stored as supplied at -20°C. It should be stable for at least one year.
5-ASA is supplied as a crystalline solid. A stock solution may be made by dissolving the 5-ASA in an organic solvent purged with an inert gas. 5-ASA is insoluble in ethanol, but it can be dissolved in organic solvents such as DMSO and dimethyl formamide (DMF). The solubility of 5-ASA in DMSO is approximately 4 mg/ml and in DMF it is approximately 1.6 mg/ml. In both of these solvents the 5-ASA forms a yellow solution.
Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of 5-ASA can be prepared by directly dissolving the crystalline compound in aqueous buffers. The solubility of 5-ASA in PBS (pH 7.2) is approximately 1.7 mg/ml. We do not recommend storing the aqueous solution for more than one day.
5-ASA is a metabolite of sulfasalazine, a drug used in the treatment of Crohn′s disease and ulcerative colitis. Whereas sulfasalazine is a potent and selective inhibitor of NF-κB, 5-ASA does not appear to inhibit NF-κB.1 In whole blood assays, 5-ASA proves to be a weak, non-selective inhibitor of both COX-1 and COX-2 with IC50 values of 410 and 61 μM, respectively. In ionopore-stimulated colonic mucosal cells, 1 mM 5-ASA does not inhibit prostagladin E2 (PGE2) production, but does reduce leukotriene B4 (LTB4) synthesis approximately 50% in these cells. In ionophore-stimulated human leukocytes, 400 μM 5-ASA reduces LTB4 production approximately 20%. 5-ASA does not inhibit 15-hydroxy PGDH at concentrations up to 50 μM.

Appearance :

Powder

Physical State :

Solid

Solubility :

Soluble in 1 M hydrochloric acid (50 mg/ml), water (0.84 g/l at 20° C), alcohol, DMSO (~4 mg/ml), DMF (~1.6 mg/ml), PBS(pH=7.2) (~1.7 mg/ml), methanol, water (1.7 mg/ml at 25° C), and ethanol (31 mg/ml at 25° C). Insoluble in diethyl ether, and n-octanol.

Storage :

Store at 4° C

Melting Point :

275-280° C (lit.)(dec.)

Boiling Point :

403.86° C at 760 mmHg (Predicted)

Density :

1.57 g/cm³

Refractive Index :

n²⁰_D ~1.69 (Predicted)

IC50 :

Epidermal growth factor receptor erbB1: IC₅₀ = 17.6 µM (mouse); COX-1: IC₅₀ = 410 µM; COX-2: IC₅₀ = 61 µM; ATPase activity of Tag : IC₅₀ = 8.29 µM

pK Values :

pK_a: 1.90, pK_b: 5.43 (Predicted)

WGK Germany :

2

RTECS :

VO1400000

PubChem CID :

Merck Index :

14: 5904

MDL Number :

MFCD00007877

EC Number :

201-919-1

Beilstein Registry :

2090421

SMILES :

NC1=CC(C(O)=O)=C(O)C=C1