133-11-9 Usage
Description
Phenyl-4-aminosalicylate, also known as p-aminosalicylic acid (PAS), is an organic compound with the chemical formula C7H7NO3. It is a white powder and is used as a reactant in the synthesis of p-aminosalicylic ester imines, which exhibit antitubercular activity. It is also known by the brand name Pheny-Pas-Tebamin (Purdue Frederick).
Uses
Used in Pharmaceutical Industry:
Phenyl-4-aminosalicylate is used as an antitubercular agent for the treatment of tuberculosis. It is used as a reactant in the synthesis of p-aminosalicylic ester imines, which have antitubercular activity.
Used in Antibacterial Applications:
Phenyl-4-aminosalicylate is used as a tuberculostatic agent, which helps in inhibiting the growth of Mycobacterium tuberculosis, the bacteria responsible for causing tuberculosis.
Chemical Properties:
Phenyl-4-aminosalicylate is a white powder with the chemical formula C7H7NO3.
Originator
Pheny-Pas-Teb-Amin ,Purdue Frederick, US,1959
Manufacturing Process
183 g of p-nitrosalicylic acid are dissolved in 564 g of phenol by heating to 140°C to 150°C on an oil bath. When all the p-nitrosalicylic acid is dissolved, 153 g of phosphorus oxychloride are run in, drop by drop, over a period of about 2 hours, while maintaining the temperature at about 150°C. The still warm mixture is run into 2 liters of water with agitation. The precipitate formed is filtered off, washed with water until phenol is removed and then dried.There are thus obtained 250 g of 2-hydroxy-4-nitrophenylbenzoate which melts at 154°C to 155°C.In a hydrogenation autoclave are introduced 92 g of 2-hydroxy-4nitrophenylbenzoate preceded by 200 cc of ethyl acetate; Raney nickel, obtained from 30 g of alloy, is added with 300 cc of ethyl acetate. Hydrogenation under pressure (100 to 120 kg) at ordinary temperature is carried out during a period of about 12 hours. The nickel is filtered off and the ethyl acetate is removed by distillation on the water bath under a vacuum of 300 mm. There is thus obtained 80 g of crude damp 2-hydroxy-4amnophenylbenzoate which after recrystallization from isopropyl alcohol melts at 153°C.
Therapeutic Function
Antibacterial (tuberculostatic)
Purification Methods
Crystallise the ester from EtOH (m 155o, also 149-150.5o), aqueous EtOH (m 147-149o), or isopropanol. It is tuberculostatic.[Beilstein 13 IV 1979.]
Check Digit Verification of cas no
The CAS Registry Mumber 133-11-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 3 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 133-11:
(5*1)+(4*3)+(3*3)+(2*1)+(1*1)=29
29 % 10 = 9
So 133-11-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H11NO3/c14-9-6-7-11(12(15)8-9)13(16)17-10-4-2-1-3-5-10/h1-8,15H,14H2