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57410

Sigma-Aldrich

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:
830-96-6
Molecular Weight:
189.21
Beilstein:
147733
EC Number:
212-600-1
MDL number:
MFCD00005660
UNSPSC Code:
12352100
PubChem Substance ID:
57651623
NACRES:
NA.22

Assay

≥97.0% (T)

form

solid

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

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

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.

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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Wanguo Wei et al.
Bioorganic & medicinal chemistry letters, 19(24), 6926-6930 (2009-11-10)
New small molecule inhibitors of HCV were discovered by screening a small library of indoline alkaloid-type compounds. An automated assay format was employed which allowed identification of dimerization inhibitors of core, the capsid protein of the virus. These compounds were
Francis Giraud et al.
Bioorganic & medicinal chemistry letters, 20(17), 5203-5206 (2010-07-27)
N-aryl-3-(indol-3-yl)propanamides were synthesized and their immunosuppressive activities were evaluated. This study highlighted the promising potency of 3-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-(4-nitrophenyl)propanamide 15 which exhibited a significant inhibitory activity on murine splenocytes proliferation assay in vitro and on mice delayed-type hypersensitivity (DTH) assay in vivo.
Ragan, J. A.; et al.
Organic Process Research & Development, 13, 186-186 (2009)
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
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