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A3537

Sigma-Aldrich

5-Aminosalicylic acid

powder, ≥99%

Synonym(s):

5-AS, 5-Amino-2-hydroxybenzoic acid, Mesalamine

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About This Item

Linear Formula:
H2NC6H3-2-(OH)CO2H
CAS Number:
Molecular Weight:
153.14
Beilstein:
2090421
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83

product name

5-Aminosalicylic acid, ≥99%

Quality Level

Assay

≥99%

form

powder

color

off-white to gray

mp

275-280 °C (dec.) (lit.)

solubility

1 M HCl: 50 mg/mL, clear, yellow to brown

storage temp.

2-8°C

SMILES string

Nc1ccc(O)c(c1)C(O)=O

InChI

1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

InChI key

KBOPZPXVLCULAV-UHFFFAOYSA-N

Gene Information

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Application

5-Aminosalicylic acid (5-ASA) has been used:
  • to synthesize 5-formyl-aminosalicylate-inulin to quantify its release during in vitro digestion and fermentation and compare the in vitro fermentation properties of the conjugated inulin to native inulin
  • in cell adhesion assay to study its effects on E-cadherin glycosylation and membranous turnover
  • to evaluate its effects on the neutrophilic inflammation index (NII) phenotype to study the effectiveness of the high cholesterol diet-gut inflammation (HCD-GI) platform

5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.

Biochem/physiol Actions

5-Aminosalicylic acid (5-ASA) is a first-line medicine, used to treat inflammatory bowel diseases like ulcerative colitis (UC). It has a high-efficiency rate in maintenance and induction of remission. 5-ASA is an active component of sulfasalazine and also consists of the carbohydrate polymer, inulin. It might exhibit anti-oxidant activity to lessen tissue injury. 5-ASA is vital for the prevention of T cell activation and proliferation. It negatively regulates cyclooxygenase and lipoxygenase pathways and lowers the formation of prostaglandins and leukotrienes. 5-ASA stimulates the membranous expression of E-cadherin and boosts intercellular adhesion.

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Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Raffi Karagozian et al.
Therapeutics and clinical risk management, 3(5), 893-903 (2008-05-14)
Ulcerative colitis (UC) is a chronic inflammatory condition of unclear etiology affecting the large bowel, most commonly the rectum and extending proximally in a continuous fashion. The overall principle in the pathophysiolgy of ulcerative colitis is the dysregulation of the
Agnieszka Kempinska-Podhorodecka et al.
Scientific reports, 11(1), 10134-10134 (2021-05-14)
Primary sclerosing cholangitis (PSC) is commonly accompanied by ulcerative colitis (UC). MicroRNA-506 modulates expression of genes which are essential for sphingosine-mediated signaling pathway and intestinal mucosa protection. We investigated whether miR-506 and its target genes are involved in phenotypic presentations
In vitro digestion and fermentation of 5-formyl-aminosailcylate-inulin: A potential prodrug of 5-aminosalicylic acid
Hartzell AL, et al.
Bioactive Carbohydrates and Dietary Fibre (2013)
Maximilian Hoffmann et al.
Naunyn-Schmiedeberg's archives of pharmacology, 394(3), 533-543 (2020-10-17)
Cardiovascular diseases are exacerbated and driven by cardiac fibrosis. TGFβ induces fibroblast activation and differentiation into myofibroblasts that secrete excessive extracellular matrix proteins leading to stiffening of the heart, concomitant cardiac dysfunction, and arrhythmias. However, effective pharmacotherapy for preventing or
Bei Ye et al.
World journal of gastrointestinal pharmacology and therapeutics, 6(4), 137-144 (2015-11-12)
Oral mesalazine (also known as mesalamine) is a 5-aminosalicylic acid compound used in the treatment of mild to moderate ulcerative colitis, with high rates of efficacy in induction and maintenance of remission. The therapeutic effect of mesalazine occurs topically at

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