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220027

Sigma-Aldrich

3-Indolepropionic acid

ReagentPlus®, 99%

Synonym(s):

3-(3-Indolyl)propanoic acid, IPA, Indole-3-propionic acid, NSC 3252, NSC 47831

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About This Item

Empirical Formula (Hill Notation):
C11H11NO2
CAS Number:
830-96-6
Molecular Weight:
189.21
Beilstein:
147733
EC Number:
212-600-1
MDL number:
MFCD00005660
UNSPSC Code:
12352100
PubChem Substance ID:
24853161
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

Assay

99%

form

powder

mp

134-135 °C (lit.)

solubility

ethanol: soluble 50 mg/mL, clear, yellow to orange

SMILES string

OC(=O)CCc1c[nH]c2ccccc12

InChI

1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)

InChI key

GOLXRNDWAUTYKT-UHFFFAOYSA-N

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General description

3-Indolepropionic acid is an effective inhibitor of aggregation of misfolded β-amyloid protein (Abeta). Three-component one-pot procedure has been reported to assemble 3-indolepropionic acids.

Application

Reactant for preparation of:
  • Fluorescent analogues of strigolactones
  • Anti-tumor agents
  • Melanocortin receptors ligands
  • Immunosuppressive agents
  • Iinhibitors of hepatitis C virus
  • Histamine H4 receptor agonists
  • NR2B/NMDA receptor antagonists
  • CB1 Antagonist for the treatment of obesity
  • Antibacterial agents
  • Inhibitor of TGF-β receptor binding

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Xun Cheng et al.
Analytical chemistry, 77(21), 7012-7015 (2005-11-01)
Alzheimer's disease is the most common cause of the loss of cognitive function among the elderly, and the aggregation and deposition of misfolded beta-amyloid protein (Abeta) contribute to this progressive central nervous system decline. Therefore, compounds that inhibit or even
Mauro F A Adamo et al.
Organic letters, 9(2), 303-305 (2007-01-16)
A three-component one-pot procedure (3-MC) was developed to assemble 3-indolepropionic acids from commercially available materials. This new methodology affords the title compounds in high yields and without the use of chromatography. [reaction: see text].
K L Borden et al.
European journal of biochemistry, 202(2), 459-470 (1991-12-05)
The antirepressor indole 3-propanoate has been shown by X-ray crystallography to bind in a different orientation compared with the natural corepressor for the tryp repressor, L-tryptophan (Lawson, C.L. & Sigler, P. B. (1988) Nature 333, 869-871). This suggests a simple
Burkhard Poeggeler et al.
PloS one, 5(4), e10206-e10206 (2010-04-28)
Aging is a multi-factorial process, however, it is generally accepted that reactive oxygen species (ROS) are significant contributors. Mitochondria are important players in the aging process because they produce most of the cellular ROS. Despite the strength of the free-radical
F Mandelbaum-Shavit et al.
Antimicrobial agents and chemotherapy, 35(12), 2526-2530 (1991-12-01)
Indole-3-propionic acid (IPA), a phytohormone derivative, is a potent inhibitor of growth of Legionella pneumophila cultivated extracellularly in a chemically defined hypotonic medium and intracellularly in human monocytes. The inhibitory activity turns into bactericidal activity with increasing concentrations. The susceptibility
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