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A3537

Sigma-Aldrich

5-Aminosalicylic acid

≥99%

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Synonym(s):
5-AS, 5-Amino-2-hydroxybenzoic acid, Mesalamine
Linear Formula:
H2NC6H3-2-(OH)CO2H
CAS Number:
Molecular Weight:
153.14
Beilstein/REAXYS Number:
2090421
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.83

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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This Item
A798091392705PHR1060
5-Aminosalicylic acid ≥99%

A3537

5-Aminosalicylic acid

5-Aminosalicylic acid 95%

A79809

5-Aminosalicylic acid

Mesalamine United States Pharmacopeia (USP) Reference Standard

1392705

Mesalamine

Mesalamine Pharmaceutical Secondary Standard; Certified Reference Material

PHR1060

Mesalamine

Gene Information

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

Gene Information

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

Gene Information

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

Gene Information

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

form

powder

form

powder with small lumps

form

-

form

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-30°C

solubility

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

solubility

-

solubility

-

solubility

-

color

off-white to gray

color

-

color

-

color

-

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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Description
Pricing

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

No data available

flash_point_c

No data available

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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.
Cheng Xie et al.
BMC gastroenterology, 19(1), 138-138 (2019-08-02)
Mesalamine is a first-line drug in the treatment of inflammatory bowel diseases, while its intolerance occasionally occurs in clinical practice. Most of adverse reactions are due to the active components, which may lead to step-up treatment, but excipients are sometimes
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)

Articles

Nitroblue Tetrazolium (NBT) is used with the alkaline phosphatase substrate 5-Bromo- 4-Chloro-3-Indolyl Phosphate (BCIP) in western blotting and immunohistological staining procedures. These substrate systems produce an insoluble NBT diformazan end product that is blue to purple in color and can be observed visually.

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