5-Aminosalicylic acid

Basic information

  • Product Name:5-Aminosalicylic acid
  • CasNo.:89-57-6
  • MF:C7H7NO3

Physical and Chemical Properties

  • Purity:99%
  • Melting Point:275-280 °C (dec.)(lit.)
  • Appearance:Off-white crystals
Inquiry

Product Details

CasNo: 89-57-6

MF: C7H7NO3

Appearance: Off-white crystals

Export Top Purity 5-Aminosalicylic acid 89-57-6 In Stock

  • Molecular Formula:C7H7NO3
  • Molecular Weight:153.137
  • Appearance/Colour:Off-white crystals 
  • Vapor Pressure:3.01E-07mmHg at 25°C 
  • Melting Point:275-280 °C (dec.)(lit.) 
  • Refractive Index:1.5500 (estimate) 
  • Boiling Point:403.9 °C at 760 mmHg 
  • PKA:2.74, 5.84(at 25℃) 
  • Flash Point:198.1 °C 
  • PSA:83.55000 
  • Density:1.491 g/cm3 
  • LogP:1.25380 

5-Aminosalicylic acid(Cas 89-57-6) Usage

Description

5-Aminosalicylic acid (5-ASA), also known as mesalamine, is an anti-inflammatory drug used to treat inflammatory bowel diseases (IBD) such as ulcerative colitis and Crohn's disease. It's often used to treat mild to moderate cases of IBD, and is considered a "grandfather medication" for colitis. 5-ASA is applied topically to the large intestine's inner lining, or mucous membrane, and can also be taken orally or rectally.

Uses 5-Aminosalicylic acid (5-ASA) works by inhibiting the activity of NF-κB, scavenging oxygen free radicals, and affecting the metabolic steps of arachidonic acid. This suppresses the synthesis of prostaglandin and leukotriene, inflammatory mediator, which can help with other inflammatory cascade responses. 5-ASA was originally used to treat rheumatoid arthritis, but was found to help IBD patients during clinical trials. It's been in use since 1942, when it was combined with the antibiotic sulfapyridine to create the molecule sulphasalazine.
Indication It is used for the treatment of active ulcerative proctitis.

Therapeutic Function

Antibacterial

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

Nonflammable

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.

Drug interactions

Potentially hazardous interactions with other drugs None known

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.]

Definition

ChEBI: A monohydroxybenzoic acid that is salicylic acid which is substituted by an amino group at the 5-position.

Brand name

SALOFALK

General Description

Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) .

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

89-57-6 Relevant articles

The optimal dose of 5-aminosalicylic acid in active ulcerative colitis: A dose-finding study with newly developed mesalamine

Wolfgang Kruis Simon Bar–Meir Janos Feher Michael Vieth Roland Greinwald

Volume 1, ISSUE 1, P36-43, January 2003

The optimal dose to induce remission of ulcerative colitis is 0.5 g 5-aminosalicylic acid 3 times a day. Patients failing with this dose may benefit from an increase of the dose up to 1.0 g 3 times a day, but should also be considered for alternative treatment. A newly developed pellet formulation of 5-aminosalicylic acid has promising efficacy and excellent safety.

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp2)-H Carboxylation with CO2

Abe, Kanae,Nakada, Akinobu,Matsumoto, Takeshi,Uchijyo, Daiki,Mori, Hirotoshi,Chang, Ho-Chol

, p. 959 - 969 (2020/12/23)

Exploring new types of photochemical rea...

5-Aminosalicylic acid alters the gut microbiota and altered microbiota transmitted vertically to offspring have protective effects against colitis

Haruka Wada, Jun Miyoshi, Satoshi Kuronuma, Yuu Nishinarita, Noriaki Oguri, Noritaka Hibi, Osamu Takeuchi, Yoshihiro Akimoto, Sonny T. M. Lee, Minoru Matsuura, Taku Kobayashi, Toshifumi Hibi & Tadakazu Hisamatsu

, Scientific Reports volume 13, Article number: 12241 (2023)

Although many therapeutic options are available for inflammatory bowel disease (IBD), 5-aminosalicylic acid (5-ASA) is still the key medication, particularly for ulcerative colitis (UC). However, the mechanism of action of 5-ASA remains unclear.

89-57-6 Process route

hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

2-hydroxy-5-[1]naphthylazo-benzoic acid
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2-hydroxy-5-[1]naphthylazo-benzoic acid

5-Aminosalicylic Acid
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5-Aminosalicylic Acid

1-amino-naphthalene
134-32-7

1-amino-naphthalene

Conditions
Conditions Yield
 
 
5-nitrosalicylic acid
96-97-9

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5-Aminosalicylic Acid
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5-amino-2-hydroxy-3-sulfobenzoic acid
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5-amino-2-hydroxy-3-sulfobenzoic acid

Conditions
Conditions Yield
 
 

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