4-Aminosalicylic acid

Base Information

• Chemical Name: 4-Aminosalicylic acid
• CAS No.: 65-49-6
• Deprecated CAS: 2220148-96-7
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.137
• Hs Code.: 29225000
• European Community (EC) Number: 200-613-5
• NSC Number: 2083
• UNII: 5B2658E0N2
• DSSTox Substance ID: DTXSID2022591
• Nikkaji Number: J4.838K
• Wikipedia: 4-Aminosalicylic_acid
• Wikidata: Q229924
• NCI Thesaurus Code: C47394
• Pharos Ligand ID: DA79VXDUR24A
• Metabolomics Workbench ID: 42635
• ChEMBL ID: CHEMBL1169
• Mol file: 65-49-6.mol

Synonyms:Salicylicacid, 4-amino- (8CI);2-Hydroxy-4-aminobenzoic acid;4-Aminosalicylicacid;Entepas;Gabbropas;Osacyl;PAS (acid);Pamisyl;Para-Pas;Paramycin;Parasal;Parasalindon;Pasnodia;Propasa;Sanipirol-4;

Chemical Property of 4-Aminosalicylic acid

Chemical Property:

• Appearance/Colour: beige powder
• Melting Point: 135-145 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 380.8 °C at 760 mmHg
• PKA: 3.25(at 25℃)
• Flash Point: 184.1 °C
• PSA: 83.55000
• Density: 1.491 g/cm³
• LogP: 1.25380
• Storage Temp.: Store at 0-5°C
• Solubility.: 1.69g/l
• Water Solubility.: 2 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

4-Aminosalicylic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,T
• Hazard Codes: Xn,Xi,T
• Statements: 22-36-36/37/38-45-35-61
• Safety Statements: 26-37/39-45-53-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: C1=CC(=C(C=C1N)O)C(=O)O
• Recent ClinicalTrials: Pharmacokinetic Study of Antiretroviral Drugs and Related Drugs During and After Pregnancy
• Recent EU Clinical Trials: A randomized controlled withdrawal trial in Crohn's disease patients in long-term remission on mesalazine: the CROWN study
• Uses: Intended for use in Sigma Periodic Acid Staining Procedure, 395. Kit is intended for use with blood, bone marrow, tissue touch preparations or routine tissue sections. It is used for staining glycoproteins in polyacrylamide gels. Schiff's reagent is also sometimes used to dye organic tissues. It is been widely used for detection of a certain functional group in chemical solutions. antimycobacterial antitubercular;NF-kB inhibitor.4-Aminosalicylic acid (p-aminosalicylic acid, PAS), an antituberculosis drug, is a model active pharmaceutical ingredient to study salt and cocrystal formation in a multiple hydrogen-bonding functionality molecule with carboxylic acid, amine, and phenol groups.It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease.It is typically taken by mouth. An antibiotic used to treat tuberculosis.
• Indications: p-Aminosalicylic acid is a bacteriostatic that inhibits most tuberculous mycobacteria. In terms of tuberculostatic activity it is inferior to isoniazid and streptomycin. It is nephroand hepatotoxic, and is rarely used. A synonym of this drug is apacizin.
• Therapeutic Function: Antitubercular

Technology Process of 4-Aminosalicylic acid

There total 21 articles about 4-Aminosalicylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-hydroxy-4-nitrobenzoic acid (619-19-2) → 4-Aminosalicylic acid (65-49-6)

Guidance literature:

With aminomethyl polystyrene resin formic acid salt; zinc; In methanol; at 20 ℃; for 2h;

Reference yield:

m-Hydroxyaniline (591-27-5) → 4-Aminosalicylic acid (65-49-6)

Guidance literature:

With carbon dioxide; boric acid; potassium hydrogencarbonate; at 95 ℃; weiteres Reagens: H₂O;

DOI:10.1021/jo01104a005

Reference yield:

1,5-divinyl-1,1,3,3,5,5-hexamethyltrisiloxane (17980-39-1) → 4-Aminosalicylic acid (65-49-6)

Guidance literature:

In toluene;

upstream raw materials:

2-hydroxy-4-nitrobenzoic acid

1-amino-3-acetylamino-6-carboxy-benzene

m-Hydroxyaniline

recorcinol

Downstream raw materials:

4-amino-2-hydroxy-benzoic acid 2-morpholin-4-yl-ethyl ester

2-hydroxy-4-[2]pyridylmethylenamino-benzoic acid

2-hydroxy-4-[3]pyridylmethylenamino-benzoic acid

2-hydroxy-4-pyrrol-2-ylmethylenamino-benzoic acid

Refernces

• 1、 Shebaldova et al.. "-". . . Retrieved 1979.
• 2、 Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming. "Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications". supporting information. p. 1618 - 1629. Retrieved 2021/01/25.
• 3、 Wuensch, Christiane,Gross, Johannes,Steinkellner, Georg,Lyskowski, Andrzej,Gruber, Karl,Glueck, Silvia M.,Faber, Kurt. "Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction". . p. 9673 - 9679. Retrieved 2014/03/21.