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Merck
CN

57410

Indole-3-propionic acid

≥97.0% (T)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H11NO2
CAS Number:
Molecular Weight:
189.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-600-1
Beilstein/REAXYS Number:
147733
MDL number:
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Product Name

Indole-3-propionic acid, ≥97.0% (T)

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

SMILES string

OC(=O)CCc1c[nH]c2ccccc12

assay

≥97.0% (T)

form

solid

functional group

carboxylic acid

Quality Level

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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
Indole-3-propionic acid may be used in the synthesis of oxindole-3-propionic acid via reaction with N-bromosuccinimide in acetic acid followed by treatment with H2/Pd catalyst.

Biochem/physiol Actions

Studied as an adjunct to improve perfusion after liver transplant.
Was studied as an adjunct to improve perfusion after liver transplant.

General description

Indole-3-propionic acid can be obtained from tryptophan by deamination reaction.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Peng Xu et al.
Bioorganic & medicinal chemistry letters, 17(12), 3330-3334 (2007-04-27)
A series of novel acylide derivatives have been synthesized from erythromycin A via a facile procedure. By applying this procedure, cyclic carbonation to C-11,12 position, acylation to C-3 hydroxyl, and deprotection provided the desired acylides. These compounds showed antibacterial activity
Rosaria Gitto et al.
Bioorganic & medicinal chemistry, 17(4), 1640-1647 (2009-01-23)
A combined ligand-based and structure-based approach has previously allowed us to identify NR2B/NMDA receptor antagonists containing indole scaffold. In order to further explore the main structure activity relationships of this class of derivatives we herein report the design, synthesis and
Ragan, J. A.; et al.
Organic Process Research & Development, 13, 186-186 (2009)
Design and parallel synthesis of new bicyclic small molecules for targeting the melanocortin receptors.
Byoung J Min et al.
Advances in experimental medicine and biology, 611, 187-188 (2009-04-30)
Prandi, C.; et al.
European Journal of Organic Chemistry, 3781-3781 (2011)

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