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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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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)
Subra, G.; et al.
QSAR & Combinatorial Science, 26, 496-496 (2007)
Prandi, C.; et al.
European Journal of Organic Chemistry, 3781-3781 (2011)
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
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
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