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Merck
CN

A3537

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:
89-57-6
Molecular Weight:
153.14
Beilstein:
2090421
EC Number:
201-919-1
MDL number:
MFCD00007877
UNSPSC Code:
12352204
PubChem Substance ID:
24890780
NACRES:
NA.83

Key Documents

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Product Name

5-Aminosalicylic acid, ≥99%

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

human ... ALOX5(240), PPARG(5468), PTGS1(5742), PTGS2(5743)

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7479V
MKCT6158
MKCB9194
051M1878V
070M1603

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Vineeta Khare et al.
Biochemical pharmacology, 87(2), 312-320 (2013-11-05)
Genome wide association studies have implicated intestinal barrier function genes in the pathogenesis of ulcerative colitis. One of such loci CDH1, encoding E-cadherin, a transmembrane glycoprotein with known tumor suppressor functions, is also linked to the susceptibility to colorectal cancer.
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
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
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)
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
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