Mesalazine
5-Aminosalicylic acid
CAS: 89-57-6
Molecular Formula: C7H7NO3
Mesalazine - Names and Identifiers
| Name | 5-Aminosalicylic acid |
| Synonyms | 5-AS 5-ASA rowasa Mesalmine Mesalamine Mesalazine 5-AMINOSALICYLIC ACID 5-Aminosalicylic acid 5-amino saliclic acid Aminosalicylic acid,5- 5-Amino salicylic Acid 5-Amino salicylic acidl 5-amino-2-hydroxybenzoate 3-Carboxy-4-hydroxyaniline 5-AMINO-2-HYDROXYBENZOIC ACID 2-HYDROXY-5-AMINOBENZOIC ACID 5-Amino-2-hydroxybenzoic acid |
| CAS | 89-57-6 |
| EINECS | 201-919-1 |
| InChI | InChI=1/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)/p-1 |
| InChIKey | KBOPZPXVLCULAV-UHFFFAOYSA-N |
Mesalazine - Physico-chemical Properties
| Molecular Formula | C7H7NO3 |
| Molar Mass | 153.14 |
| Density | 1.3585 (rough estimate) |
| Melting Point | 275-280 °C (dec.) (lit.) |
| Boling Point | 276.03°C (rough estimate) |
| Flash Point | 279-281°C |
| Water Solubility | <0.1 g/100 mL at 21 ºC |
| Solubility | Soluble in hydrochloric acid, slightly soluble in hot water, micro-bath in cold water or ethanol. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | off-white to gray(powder) |
| Color | off-white to gray |
| Merck | 14,5904 |
| BRN | 2090421 |
| pKa | 2.74, 5.84(at 25℃) |
| PH | 4.0-4.1 (0.8g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with acids, acid anhydrides, acid chlorides, chloroformates, strong oxidizing agents. |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00007877 |
| Physical and Chemical Properties | Melting point 280°C DECOMPOSITION -281°C water-soluble <0.1g/100 mL at 21°C |
Mesalazine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 2 |
| RTECS | VO1400000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | Yes |
| HS Code | 29225000 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 orally in Rabbit: 2800 mg/kg LD50 dermal Rat > 5000 mg/kg |
Mesalazine - Reference
| Reference Show more | 1. Dai Yuanyuan, Alpine, Liu Yuqin, et al. Effects of Tripterygium wilfordii polyglycoside on Th17/Treg cell differentiation and balance in rats with experimental colitis [J]. Gastroenterology, 2020, v.25(02):26-31. 2. Cui Li, Ning Qing, Zhang Runtong, Liu Guoguang, Zhong Rongling, Xia Zhi, Wang Jing. Optimization of extraction conditions of polysaccharide from Scutellaria baicalensis Georgi and its effect on ulcerative colitis in mice [J]. Shandong Journal of Traditional Chinese Medicine, 2020,39(09):993-1000. 3. [IF = 5.34] Gui Zhou et al."Effects of Qing Chang coping Powder and its Effects on IL-17 Signal Pathway in HT-29 Cells and DSS-induced Mice." Phytopedicine. 2021 Jul;87:153573 4. [IF = 3.765] Hossen Imam et al."Glochidion ellipticum Wight extracts ameliorate dextran sulfate sodium-induced colitis in mice by modulating nuclear factor kappa-light-chain-enhancer of activated B cells signalling pathway."J Pharm Pharmacol. 2021 Mar;73(3):410-423 5. [IF=3.641] Ji Cao et al."Effect of dehydroepiandrosterone on the immune response and gut microbiota in dextran sulfate sodium-induced colitis mice."Mol Immunol. 2020 Feb;118:60 6. [IF=4.932] Liangjun Deng et al."(RS)-bambuterol and its enantiomers: Potential improvement of (R)-bambuterol in mice with colitis."Int Immunopharmacol. 2022 Feb;103:108501 7. [IF=6.922] Shanping Wang et al."Isosteviol Sodium Exerts Anti-Colitic Effects on BALB/c Mice with Dextran Sodium Sulfate-Induced Colitis Through Metabolic Reprogramming and Immune Response Modulation."J Inflamm Res. 2021; 14: 7107-7130 |
Mesalazine - Nature
Open Data Verified Data
white to pink crystals, about 280 °c decomposition. Soluble in hydrochloric acid, micro-in hot water, micro-in cold water or ethanol.
Last Update：2024-01-02 23:10:35
Mesalazine - Preparation Method
Open Data Verified Data
after salicylic acid and water were mixed, a mixture of 68% nitric acid and glacial acetic acid was slowly added dropwise at 50 °c with stirring. Then the temperature was raised to 70-80 ℃. The reaction solution was put into water, allowed to stand, filtered, and the filter cake was recrystallized with hot water to obtain a solid of 5-nitrosalicylic acid. Iron powder was added to the hydrochloric acid solution. After heating and boiling, add 5 A Nitro salicylic acid reaction, after further processing to obtain mesalazine. Or salicylic acid by nitration of 5 Nitro salicylic acid, and then reaction with methanesulfonyl chloride, and then hydrogenation reduction of Nitro to Amino, and finally hydrolyzed to mesalazine.
Last Update：2022-01-01 09:23:11
Mesalazine - Use
Open Data Verified Data
developed by Pharmacia AB, Switzerland, launched in 1985. Developed by SK and Fening. In 1987, it was approved by the US FDA as a drug for the treatment of colitis. Drugs for the treatment of ulcerative colitis. It has a significant inhibitory effect on the inflammation of the intestinal wall. Mesalazine can inhibit the synthesis of prostaglandins which cause inflammation and the formation of inflammatory mediators leukotrienes, and thus has a significant inhibitory effect on the inflammation of the intestinal mucosa. It has a better effect on the connective tissue of the inflamed intestinal wall. For ulcerative colitis, ulcerative proctitis and Crohn's disease.
Last Update：2022-01-01 09:23:11
Mesalazine - Reference Information
| pH range of acid-base indicator discoloration | Non-B uoresce (3.1) to light green B uoresce (4.4) |
| Decomposition | 279-281 ºC |
| Main application | , chemokine-mediated diseases, mucosal tissue disease, sleep disorders, rectoanal tenesmus, ulcerative coli|
| LogP | 0.98 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Use | ulcerative colitis therapeutic agent. dye intermediate. 5-aminosalicylic acid (5-ASA drug name Masalazine, Masalazine) is an important pharmaceutical and dye chemical raw materials, but also a treatment of chronic colitis drug sulfasalazine main raw material, it itself has a similar therapeutic effect. Since 5-aminosalicylic acid has three active reactive groups of hydroxyl and carboxyl groups on the ring, it can carry out a variety of reactions. Therefore, in the dye industry, it can be used to produce a variety of reactive dyes with excellent quality. It is also used in the manufacture of light-sensitive paper. used as an intermediate of azo and sulfur dyes, and used in the manufacture of photosensitive paper has a significant inhibitory effect on the inflammation of the intestinal wall; mesalazine can inhibit the synthesis of prostaglandins that cause inflammation and the formation of inflammatory mediators leukotrienes, thus significantly inhibiting the inflammation of the intestinal mucosa. It has a better effect on the connective tissue of the inflamed intestinal wall. For ulcerative colitis, ulcerative proctitis and Crohn's disease. 5-aminosalicylic acid is a peroxidase substrate suitable for ELISA analysis. This substrate produces a brown, soluble end product which can be read spectrophotometrically at 450nm. The reaction was stopped by addition of 3N NaOH and then read at 550nm. |
| production method | The M-nitrosalicylic acid is obtained by the action of zinc powder and hydrochloric acid, or by the method of electrolytic reduction of nitrobenzoic acid. Method 1: After salicylic acid and water were mixed, a mixture of 68% nitric acid and glacial acetic acid was slowly added dropwise at 50 °c with stirring. Then the temperature was raised to 70-80 ℃. The reaction solution was poured into water and allowed to stand at 5 °c. After filtration, the filter cake was recrystallized from hot water to give 5-nitrosalicylic acid as a solid in 40% yield. Iron powder was added to the hydrochloric acid solution at 60 °c. After heating and boiling, add 1/4 of 5-nitrosalicylic acid. After vigorous stirring, the remainder of the nitroxide and iron powder were added alternately in batches. After addition, the reaction was carried out at 102 °c. Adjust to strong alkalinity with 50% sodium hydroxide while hot, and filter. The filter cake was washed with hot water, and the filtrate and washings were combined, followed by addition of sodium hydrosulfite and acidification with 40% sulfuric acid to pH 4. Cool, filter, dry, dissolve it in hot water with sodium bisulfite, and boil with charcoal. Hot filtration was performed, and the filter cake was washed with a small amount of hot water. The filtrate and wash were combined and placed at 5 °c. The crystals were collected by filtration, washed fully with ice water, dried, A white needle-like mesalazine crystal with a melting point of 278 ° C. (decomposition) was obtained. Method 2: Salicylic acid was nitrated to produce 5-nitrosalicylic acid, and then reacted with methanesulfonyl chloride to protect phenolic hydroxyl groups, and then hydrogenated to reduce the nitro group to amino group, and finally hydrolyzed to obtain mesalazine. Method 3: The diazonium salt was obtained by diazotization of aniline, which was added to a solution of salicylic acid, sodium carbonate and 40% sodium hydroxide, vigorously stirred at 0~6 °c and maintained at pH 8. Filter, wash with saturated saline, press dry. Dissolve in 40% sodium hydroxide solution, add the powder at 80~85 deg C. After the solution was completely discolored, the aniline was distilled off by steam distillation and filtered. The filtrate was adjusted to pH 6-6.5 with concentrated hydrochloric acid and allowed to stand overnight. After filtration, washing with cold water, the dried crude product was dissolved in water, concentrated hydrochloric acid was added dropwise to dissolve, and then activated carbon was added and heated to boiling. Filtration, cooling and adjustment to Ph 2-3 with dilute sodium hydroxide. Filtration, cold water washing, Vacuum drying at room temperature to obtain gray-white mesalazine solid, melting point 278 ℃ (decomposition), the total yield of 45.9%. Method 4: p-aminophenol and an appropriate amount of catalyst were stirred at a CO2 pressure of 2.0-130 MPa and 190-°c. Cool to room temperature, add water and powder, and stir. Cool to 0~3 ℃, filter insoluble matter, Wash. The washings and filtrates were combined, adjusted to PH 3-4 with hydrochloric acid, filtered and washed with water to obtain mesalazine crude product. Water, sodium bicarbonate and sodium bisulfite were added to the crude product, heated to 50-60 ° C. And completely dissolved, and then activated carbon was added and boiled. Filtration, cooling and adjustment to pH 3.5 with dilute hydrochloric acid. Filtration, washing with water, and drying gave an off-white fine product with a yield of 91.1% and a content of 99.2%. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | intraperitoneal-mouse LD50: 5000 mg/kg; Oral-mouse LDL0: 313 mg/kg |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| spontaneous combustion temperature | 280°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:04:16
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