5-Aminosalicylic acid CAS 89-57-6
Introduction：Basic information about 5-Aminosalicylic acid CAS 89-57-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
5-Aminosalicylic acid Basic informationIndication References
| Product Name: | 5-Aminosalicylic acid |
| Synonyms: | 5-Aminosalicylic acid, 98.5%, IKK inhibitor;2-HYDROXY-5-AMINOBENZOIC ACID;3-Carboxy-4-hydroxyaniline;5-AMINO-2-HYDROXYBENZOIC ACID;5-AMINOSALICYLIC ACID;5-ASA;5-AS;rowasa |
| CAS: | 89-57-6 |
| MF: | C7H7NO3 |
| MW: | 153.14 |
| EINECS: | 201-919-1 |
| Product Categories: | API;CITANEST;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Aromatics;Pharmaceuticals;Carboxylic Acids;Phenyls & Phenyl-Het;Fluorescent;Carboxylic Acids;Phenyls & Phenyl-Het;Organic acids;Various Metabolites and Impurities;Fendosal;Intermediates & Fine Chemicals;Metabolites & Impurities;FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts |
| Mol File: | 89-57-6.mol |
5-Aminosalicylic acid Chemical Properties
| Melting point | 275-280 °C (dec.) (lit.) |
| Boiling point | 276.03°C (rough estimate) |
| density | 1.3585 (rough estimate) |
| bulk density | 300kg/m3 |
| vapor pressure | 0Pa at 25℃ |
| refractive index | 1.5500 (estimate) |
| Fp | 279-281°C |
| storage temp. | 2-8°C |
| solubility | Soluble in dimethyl sulfoxide. |
| pka | 2.74, 5.84(at 25℃) |
| form | tablets |
| color | off-white to gray |
| PH | 4.0-4.1 (0.8g/l, H2O, 20℃) |
| PH Range | Non-B uorescence (3.1) to light green B uorescence (4.4) |
| Water Solubility | <0.1 g/100 mL at 21 ºC |
| Decomposition | 279-281 ºC |
| Merck | 14,5904 |
| BRN | 2090421 |
| BCS Class | 4 |
| Stability: | Stable. Incompatible with acids, acid anhydrides, acid chlorides, chloroformates, strong oxidizing agents. |
| Major Application | Detergent, hair dyes, prevention of colorectal cancer, treating inflammatory bowel disease, autoimmune disorders, gastrointestinal inflammation, chemokine-mediated diseases, mucosal tissue disorder, sleep disorders, rectoanal tenesmus, ulcerative colitis |
| InChI | 1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11) |
| InChIKey | KBOPZPXVLCULAV-UHFFFAOYSA-N |
| SMILES | Nc1ccc(O)c(c1)C(O)=O |
| LogP | 0.98 at 25℃ |
| CAS DataBase Reference | 89-57-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Mesalamine(89-57-6) |
| EPA Substance Registry System | Benzoic acid, 5-amino-2-hydroxy- (89-57-6) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-52/53 |
| Safety Statements | 26-36-24/25-61-37/39 |
| WGK Germany | 2 |
| RTECS | VO1400000 |
| F | 8-10-23 |
| Autoignition Temperature | 280 °C |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29225000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 89-57-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2800 mg/kg LD50 dermal Rat > 5000 mg/kg |
| Indication | It is used for the treatment of active ulcerative proctitis. |
| References |
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| Description | 5-Aminosalicylic acid (5-ASA), also known as mesalazine or mesalamine, is a metabolite and potential pharmacologically active component of sulphasalazine, a drug used in the treatment of Crohn’s disease and ulcerative colitis. However, the mechanism by which this drug works has not been established. 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 ionophore-stimulated colonic mucosal cells, 1 mM 5-ASA does not inhibit prostaglandin E2 (PGE2) production, but does reduce leukotriene B4 (LTB4) synthesis approx. 50%. 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. |
| Chemical Properties | Off-White to pink crystals, melting point about 280 ℃ (decomposition). Soluble in hydrochloric acid, slightly soluble in hot water, and slightly bath in cold water or ethanol. In the manufacture of light-sensitive paper, azo and sulfur dyes. |
| Originator | Radcliffe Infirmary (United Kingdom) |
| Uses | 5-Aminosalicylic acid is used in the preparation of gastrointestinal anti-inflammatory agents. It is a metabolite of sulfasalazine. It acts as a drug involved in the treatment of Crohn's disease and ulcerative colitis. Further, it is used to make dyes and light-sensitive papers. |
| Definition | ChEBI: Mesalamine is a monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position. It has a role as a non-steroidal anti-inflammatory drug. It is an aromatic amine, an amino acid, a member of phenols, a monocarboxylic acid and a monohydroxybenzoic acid. It is functionally related to a salicylic acid. It is a conjugate acid of a mesalaminate(1-). |
| Preparation | Preparation by reduction of m-nitrobenzoic acid with Zn dust and HCl. |
| Application | 5-Aminosalicylic acid (5-ASA) has been used to synthesize 5-formyl-aminosalicylate-inulin to quantify its release during in vitro digestion and fermentation and compare the in vitro fermentation properties of the conjugated inulin to native inulin. It is also used in cell adhesion assay to study its effects on E-cadherin glycosylation and membranous turnover. This compound is used to evaluate its effects on the neutrophilic inflammation index (NII) phenotype to study the effectiveness of the high cholesterol diet-gut inflammation (HCD-GI) platform.5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm. |
| Manufacturing Process | Procedure A: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. To this solution 2 g of Raney nickel were added. The mixture was heated-up to reflux and hydrazine hydrate (40 mL, 80% in water, 64 mmol) was added dropwise during 3-4 hrs. The reflux was maintened until HPLC showed the disappearance of the starting material and the complete reduction of 5-nitrosalicylic acid (3-4 hrs). The hot mixture was filtered under nitrogen and the solution was collected. The solution was cooled to 40°C and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with water, and dried at 60-70°C. 5-Aminosalicylic acid was obtained in 89% yield. Procedure B: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. The solution was charged in a stainless steel autoclave and 2 g of Raney nickel are added. Hydrogen was introduced into the autoclave reaching a pressure of 8 atm. The mixture was heated-up to 100°C. The temperature was maintained until HPLC-test 5-aminosalicylic acid showed the disappearance of the starting material and the complete reduction of 5- aminosalicylic acid (6-8 hrs). Hydrogen was purged and replaced by nitrogen. The hot mixture was filtered under nitrogen, the filtrate was cooled to 40°C, and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of the 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with ion depleted water, and dried at 60-70°C. |
| Brand name | SALOFALK |
| Therapeutic Function | Antibacterial |
| General Description | Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) . |
| Air & Water Reactions | Sensitive to moisture. Water insoluble. |
| Reactivity Profile | 5-Aminosalicylic acid is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. |
| Fire Hazard | Flash point data for 5-Aminosalicylic acid are not available; however, 5-Aminosalicylic acid is probably combustible. |
| Flammability and Explosibility | Non flammable |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Biochem/physiol Actions | 5-Aminosalicylic acid (5-ASA) is a first-line medicine, used to treat inflammatory bowel diseases like ulcerative colitis (UC). It has a high-efficiency rate in maintenance and induction of remission. 5-ASA is an active component of sulfasalazine and also consists of the carbohydrate polymer, inulin. It might exhibit anti-oxidant activity to lessen tissue injury. 5-ASA is vital for the prevention of T cell activation and proliferation. It negatively regulates cyclooxygenase and lipoxygenase pathways and lowers the formation of prostaglandins and leukotrienes. 5-ASA stimulates the membranous expression of E-cadherin and boosts intercellular adhesion. |
| Clinical Use | Induction and maintenance of remission in ulcerative colitis |
| Side effects | 5-Aminosalicylic acid (5-ASA) is widely used to treat ulcerative colitis and is better tolerated than sulfadiazine. Common side effects of 5-ASA include nausea, vomiting, abdominal pain, headache, and rash. 5-ASA-induced myocarditis is a rare side effect with only a few case reports. 5-ASA-induced myocarditis usually occurs within 2-4 weeks of medication and causes chest pain and dyspnea. In addition, 5-ASA can aggravate bloody diarrhea in patients with Crohn's disease, which may be accompanied by decreased appetite or hair loss, and is generally uncommon. |
| Safety Profile | Poison by intraperitoneal route.Moderately toxic by ingestion. Human systemic effects byingestion: hypermotility, diarrhea, dermatitis, increasedbody temperature. When heated to decomposition it emitstoxic fumes of NOx. |
| Metabolism | The absorbed part of mesalazine is almost completely acetylated in the gut wall and in the liver to acetyl-5-aminosalicylic acid.The acetylated metabolite is excreted mainly in urine by tubular secretion, with traces of the parent compound. |
| Purification Methods | It crystallises as needles from H2O containing a little NaHSO3 to avoid aerial oxidation to the quinone-imine. The Me ester gives needles from *C6H6, m 96o, and the hydrazide has m 180-182o (from H2O). [Fallab et al. Helv Chim Acta 34 26 1951, Shavel J Amer Pharm Assoc 42 402 1953, Beilstein 14 IV 2058.] |
| References | [1] S. NUGENT. Intestinal luminal pH in inflammatory bowel disease: possible determinants and implications for therapy with aminosalicylates and other drugs[J]. Gut, 2001, 48 1: 571-577. DOI: 10.1136/gut.48.4.571 [2] BEIRANVAND M. A review of the biological and pharmacological activities of mesalazine or 5-aminosalicylic acid (5-ASA): an anti-ulcer and anti-oxidant drug.[J]. Inflammopharmacology, 2021: 1279-1290. DOI: 10.1007/s10787-021-00856-1 [3] C SCHMIDT. The effect of 5-aminosalicylate and para-aminosalicylate on the synthesis of prostaglandin E2 and leukotriene B4 in isolated colonic mucosal cells.[J]. Current Medical Research and Opinion, 1996, 13 7: 417-425. DOI: 10.1185/03007999609111561 |
5-Aminosalicylic acid Preparation Products And Raw materials
| Raw materials | Sodium carbonate-->ZINC-->Water-->Sodium dithionite-->Methanesulfonyl chloride-->Salicylic acid-->Tyramine-->5-Nitrosalicylic acid-->Hydrogen-->Hydrazine hydrate-->Aluminium-nickel |
| Preparation Products | Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul-->Sulfasalazine-->METHYL 5-AMINOSALICYLATE-->BOC-3-AMINOBENZOIC ACID-->OLSALAZINE-->Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul-->tetrasodium 2-[[2-amino-6-[[4-[[4-[(3-carboxylato-4-hydroxyphenyl)azo]-7-sulphonato-1-naphthyl]azo]-2,5-dimethoxyphenyl]azo]-5-hydroxy-7-sulphonato-1-naphthyl]azo]-5-nitrobenzoate |
