ChemicalBook > CAS DataBase List > 4-Aminosalicylic acid

4-Aminosalicylic acid

Product Name
4-Aminosalicylic acid
CAS No.
65-49-6
Chemical Name
4-Aminosalicylic acid
Synonyms
4-AMINO-2-HYDROXYBENZOIC ACID;PAS;AMINOSALICYLIC ACID;Pasa;4-Asa;P-AMINOSALICYLIC ACID;Apas;Paser;Aminox;Parasal
CBNumber
CB9679687
Molecular Formula
C7H7NO3
Formula Weight
153.14
MOL File
65-49-6.mol
More
Less

4-Aminosalicylic acid Property

Melting point:
135-145 °C (lit.)
Boiling point:
276.03°C (rough estimate)
Density 
1.3585 (rough estimate)
refractive index 
1.5500 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
1.69g/l
form 
Powder
pka
3.25(at 25℃)
color 
Colorless
PH
3.5 (1g/l, H2O, 20℃)
Water Solubility 
2 g/L (20 ºC)
Merck 
14,477
BRN 
473071
BCS Class
4/2
Stability:
Hygroscopic
CAS DataBase Reference
65-49-6(CAS DataBase Reference)
NIST Chemistry Reference
Aminosalicylic acid(65-49-6)
EPA Substance Registry System
4-Aminosalicylic acid (65-49-6)
More
Less

Safety

Hazard Codes 
Xn,Xi,T
Risk Statements 
22-36-36/37/38-45-35-61
Safety Statements 
26-37/39-45-53-36-36/37/39
RIDADR 
UN 1789 8/PG 3
WGK Germany 
2
RTECS 
VO1225000
TSCA 
Yes
HS Code 
29225000
Hazardous Substances Data
65-49-6(Hazardous Substances Data)
Toxicity
LD50 orally in mice: 4 g/kg (Bavin)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A79604
Product name
4-Aminosalicylic acid
Purity
99%
Packaging
5g
Price
$19.6
Updated
2024/03/01
Sigma-Aldrich
Product number
1026401
Product name
Aminosalicylic acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$358
Updated
2024/03/01
TCI Chemical
Product number
A0420
Product name
4-Aminosalicylic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$144
Updated
2024/03/01
TCI Chemical
Product number
A0420
Product name
4-Aminosalicylic Acid
Purity
>98.0%(T)
Packaging
100g
Price
$431
Updated
2024/03/01
Alfa Aesar
Product number
B23289
Product name
4-Aminosalicylic acid, 98+%
Packaging
100g
Price
$50.65
Updated
2024/03/01
More
Less

4-Aminosalicylic acid Chemical Properties,Usage,Production

Chemical Properties

beige powder

Originator

Pamisyl,Parke Davis,US,1948

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.

Uses

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.

Uses

An antibiotic used to treat tuberculosis.

Definition

ChEBI: An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.

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.

Application

4-Aminosalicylic acid (4-ASA) can be used in the synthesis of:
Azo derivatives of 4-ASA with anti-inflammatory effects.
Ammonium 4-aminosalicylate salt polymorphs which are used as pharmaceutical ingredients.
Salicylic acid-triazole analogs which are used as quorum sensing inhibitors against Pseudomonas aeruginosa.

Manufacturing Process

As described in US Patent 427,564, aminosalicylic acid may be prepared from m-aminophenol by heating with ammonium carbonate in solution under pressure.
Alternatively, aminosalicylic acid may be made from sodium p-aminosalicylate as described in US Patent 2,844,625 as follows: 196 grams of commercial sodium para-aminosalicylate (18.5% H2O) was dissolved in 196 ml of water and 150 ml of isopropanol. 6 grams of sodium bisulfite was dissolved in the solution and the solution filtered. While stirring and keeping the temperature between 25-31°C, seven grams of 85% formic acid and 27.5 grams of 95% sulfuric acid in 150 ml of water was added during 1 ? hours. The mixture was stripped 1 hour longer, cooled to 23°C and filtered. The filter cake was washed with 100 cubic centimeters of water, further washed with 100 cc of 25% isopropanol and 100 cc of water, and vacuum dried to constant weight at 45- 50°C. Weight of p-aminosalicylic acid was 76.5 grams (92.7% yield) exhibiting a bulk density of 47 cc/oz.

brand name

Parasal (Panray); Paser (Jacobus).

Therapeutic Function

Antitubercular

General Description

4-Aminosalicylic acid occurs as a white to yellowish white crystalline solid that darkens on exposure to light or air. It is slightly soluble in water but more soluble in alcohol. Alkali metal salts and the nitric acid salt are soluble in water, but the salts of hydrochloric acid and sulfuric acid are not. The acid undergoes decarboxylation when heated. An aqueous solution has a pH of approximately 3.2. PAS is administered orally in the form of the sodium salt, usually in tablet or capsule form. Symptoms of gastrointestinal irritation are common with both the acid and the sodium salt. Various enteric-coated dosage forms have been used in an attempt to overcome this disadvantage. Other forms that are claimed to improve gastrointestinal tolerance include the calcium salt, the phenyl ester, and a combination with an anion exchange resin (Rezi-PAS). An antacid such as aluminum hydroxide is frequently prescribed. The oral absorption of PAS is rapid and nearly complete, and it is widely distributed into most of the body fluids and tissues, with the exception of the CSF, in which levels are significantly lower.It is excreted primarily in the urine as both unchanged drug and metabolites.

Biological Activity

4-Aminosalicylic acid is an antimetabolite of p-aminobenzoic acid (PABA) that has antibacterial activity.It is active against streptomycin-sensitive and -resistant strains of M. tuberculosis (MICs = 0.78 and 0.39 μg/ml, respectively), an effect that can be reversed by PABA. 4-Aminosalicylic acid is an alternative substrate for mycobacterial dihydropteroate synthase (FolP1) and misincorporation into the folate pathway leads to accumulation of several folate-dependent metabolites including serine, homocysteine, dUMP, and AICAR, markers of folate pathway inhibition, in a concentration-dependent manner. It reverses manganese-induced increases in rat hippocampal levels of NOD-like receptor protein 3 (NLRP3), cleaved caspase-1, and phosphorylated p65, markers of NLRP3 inflammasome-dependent pyroptosis, when administered at a dose of 300 mg/kg. 4-Aminosalycilic acid is also a building block that has been used in the synthesis of luminescent lanthanide complexes. Formulations containing 4-aminosalicylic acid have been used in the treatment of tuberculosis.

Mechanism of action

p-aminosalicylic acid is thought to act as an antimetabolite interfering with the incorporation of p-aminobenzoic acid into folic acid. When coadministered with INH, PAS is found to reduce the acetylation of INH, itself being the substrate for acetylation, thus increasing the plasma levels of INH. This action may be especially valuable in patients who are rapid acetylators.

Safety Profile

Moderately toxic ingestion andother routes. An eye irritant. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Synthesis

p-Aminosalicylic acid, 5-amino-2-hydroxybenzoic acid (34.1.22), is synthesized in a Kolbe reaction, which consists of direct interaction of m-aminophenol with potassium bicarbonate and carbon dioxide while heating at a moderate pressure of 5¨C10 atm.

Metabolism

p-aminosalicylic acid is extensively metabolized by acetylation of the amino group and by conjugation with glucuronic acid and glycine at the carboxyl group. It is used primarily in cases of resistance, retreatment, and intolerance of other agents and is available from the CDC.

Purification Methods

Crystallise the acid from EtOH. [Beilstein 14 IV 1967.]

4-Aminosalicylic acid Preparation Products And Raw materials

Raw materials

2,4-DINITROPHENYLACETIC ACID 1-Butyl nitrite Sodium sulfide Sodium sulfite 4-Nitrosalicylic acid Carbon dioxide Potassium hydroxide solution Sodium Methoxide METHYL 2,4-DINITROPHENYLACETATE Nitric acid Esterified product 3-Aminophenol 2-Cyanophenol Phenylacetic acid

Preparation Products

4-Chlorosalicylic acid Methyl 4-acetamido-2-methoxybenzoate optical plastics based on coplymer of diene macromolecule METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE
More
Less

4-Aminosalicylic acid Suppliers

Americas 1 Belgium 2 Canada 2 China 448 Europe 3 Germany 5 India 39 Japan 4 Slovakia 1 Switzerland 1 Ukraine 2 United Kingdom 12 United States 53 Global 573
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
Alfa Chemistry
Tel
1-516-6625404
Fax
1-516-927-0118
Email
support@alfa-chemistry.com
Country
United States
ProdList
9171
Advantage
60
AbaChemScene
Tel
732-484-9848
Fax
888-484-5008
Email
sales@chemscene.com
Country
United States
ProdList
3982
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63687
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
United States Biological
Tel
--
Fax
--
Email
sales@advtechind.com
Country
United States
ProdList
6075
Advantage
58
Alfa Chemistry
Tel
--
Fax
--
Email
info@Alfa-Chemistry.com
Country
United States
ProdList
6814
Advantage
0
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Frontier Scientific, Inc.
Tel
--
Fax
--
Email
sales@frontiersci.com
Country
United States
ProdList
6222
Advantage
86
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Accela ChemBio Inc.
Tel
--
Fax
--
Email
info@accelachem.com
Country
United States
ProdList
1054
Advantage
50
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Ivy Fine Chemicals
Tel
--
Fax
--
Email
sales@ivychem.com
Country
United States
ProdList
6493
Advantage
58
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
ChemService Inc.
Tel
--
Fax
--
Country
United States
ProdList
6379
Advantage
68
Beta Pharma, Inc.
Tel
--
Fax
--
Email
sales@betapharma.com
Country
United States
ProdList
6226
Advantage
60
Ryan Scientific, Inc.
Tel
--
Fax
--
Email
ryan.reichlyn@ryansci.com
Country
United States
ProdList
6439
Advantage
60
Alfa Aesar
Tel
--
Fax
--
Email
tech@alfa.com
Country
United States
ProdList
6814
Advantage
81
Chem-Impex International, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6730
Advantage
64
INDOFINE Chemical Company, Inc.
Tel
--
Fax
--
Email
chemical@indofinechemical.com
Country
United States
ProdList
6176
Advantage
69
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
Loba Chemie Pvt. Ltd.
Tel
--
Fax
--
Country
United States
ProdList
1945
Advantage
71
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
NetQem
Tel
--
Fax
--
Email
sales@netqem.us
Country
United States
ProdList
1641
Advantage
38
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
Spectrum Chemicals & Laboratory Products
Tel
--
Fax
--
Email
sales@spectrumchemical.com
Country
United States
ProdList
6699
Advantage
77
Crescent Chemical Co., Inc.
Tel
--
Fax
--
Email
sales@creschem.com
Country
United States
ProdList
4597
Advantage
68
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
Electron Microscopy Sciences
Tel
--
Fax
--
Email
sgkcck@aol.com
Country
United States
ProdList
672
Advantage
81
Medical Chemical Corporation
Tel
--
Fax
--
Country
United States
ProdList
114
Advantage
71
Pfaltz & Bauer, Inc.
Tel
--
Fax
--
Email
sales@pfaltzandbauer.com
Country
United States
ProdList
6828
Advantage
72
City Chemicals Corporation
Tel
--
Fax
--
Country
United States
ProdList
6460
Advantage
72
J.T. Baker-A Division of Mallinckrodt Baker, Inc.
Tel
--
Fax
--
Country
United States
ProdList
1066
Advantage
82
Fisher Scientific
Tel
--
Fax
--
Email
sales@fishersci.com
Country
United States
ProdList
2337
Advantage
86
ChemPacific Corporation
Tel
--
Fax
--
Email
sales@chempacific.com
Country
United States
ProdList
6891
Advantage
51
Wilshire Chemical Company Inc.
Tel
--
Fax
--
Email
WilshrChem@AOL.COM
Country
United States
ProdList
3498
Advantage
58
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
RAL Diagnostic Stains and Reagents Corporation
Tel
--
Fax
--
Email
biostains@yahoo.com
Country
United States
ProdList
79
Advantage
30
More
Less

View Lastest Price from 4-Aminosalicylic acid manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
4-Aminosalicylic acid 65-49-6
Price
US $0.00/Kg/Drum
Min. Order
25KG
Purity
98.5%min
Supply Ability
20tons/month
Release date
2021-06-04
Hebei Chuanghai Biotechnology Co,.LTD
Product
4-Aminosalicylic acid 65-49-6
Price
US $9.00/KG
Min. Order
1KG
Purity
99.8%
Supply Ability
100tons
Release date
2024-08-15
Hebei Weibang Biotechnology Co., Ltd
Product
4-Aminosalicylic acid 65-49-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2021-09-28

65-49-6, 4-Aminosalicylic acidRelated Search:

3-Hydroxybenzoic acid Salicylic acid Butylparaben 4-Hydroxybenzoic acid 4-Aminobenzoic acid 4-Amino-3-hydroxybenzoic acid Methylparaben 5-Amino-o-cresol Acetylsalicylic acid Acetaminophen Methyl salicylate Glycine 4-Dimethylaminobenzoic acid 4-AMINOSALICYLIC ACID, NA SALT,4-AMINOSALICYLIC ACID SODIUM DIHYDRATE Methy-5-aminosalicylate 4-Aminophenylacetonitrile Sulfanilic acid 4-Aminophenol

  • 3-Hydroxy-4-carboxyaniline
  • 4-Amino-2-hydroxbenzoicacid
  • 4-amino-2-hydroxy-benzoicaci
  • 4-Aminosalicyclic acid
  • 4-aminosalicylic
  • 2-HYDROXY-4-AMINOBENZOIC ACID
  • FUCHSIN SULFUROUS ACID
  • 4-Aminosalicylic acid;4-Amino-2-hydroxybenzoic acid; PAS
  • P-AMINOSALICYLIC ACID (PAS)
  • AMINOSALICYLICACID,USP
  • polyarylsulfone
  • 4-AMINO SALICYLIC ACID TECHNICAL GRADE
  • 4-AMINO-2-HYDROXYBENZOIC A+B4444CID
  • 4-Amino-2-hydroxybenzoic acid, PAS
  • 4-AMINOSALICYLIC ACID, 98+%
  • Aminosalicylic Acid (125 mg)
  • 4-AMinosalicylic acid, 99% 100GR
  • 4-AMinosalicylic acid, 99% 5GR
  • 4-Aminosalicylic acid,99%
  • 4-Carboxy-3-hydroxyaniline
  • Monopass
  • Mesalazine Impurity E
  • 4 - AMINO SALICYLIC ACID (TECH. GRADE) (65-49-6)
  • 4-amino-salicylicaci
  • 4-Asa
  • SCHIFF'S FUCHSIN-SULFITE REAGENT
  • SCHIFFS REAGENT
  • SCHIFF'S REAGENT
  • SCHIFF'S REAGENT FOR ALDEHYDES
  • SCHIFF REAGENT
  • SCHIFF REAGENT, HOTCHKISS AND MCMANUS
  • SCHIFF REAGENT, HOTCHKISS/MCMANUS
  • SCHIFF REAGENT SOLUTION, MODIFIED
  • PERIODIC ACID-SCHIFF
  • P-AMINOSALICYLIC ACID
  • PAS
  • 4-AMINO-2-HYDROXYBENZOIC ACID
  • 4-AMINOSALICYLIC ACID
  • AMINOSALICYLIC ACID
  • NSC 211698
  • Paser
  • 4-AMINO-2-HYDROXYBENZOIC ACID FOR SYNTHE
  • A 1909
  • Aminopar
  • Amino-pas
  • Aminox
  • Apacil
  • Apas
  • Benzoic acid, 4-amino-2-hydroxy-
  • Benzoicacid,4-amino-2-hydroxy-
  • Deapasil
  • Entepas
  • Ferrosan
  • Gabbropas
  • helipidyl
  • Hellipidyl
  • Kyselina p-aminosalicylova
  • kyselinap-aminosalicylova