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129453

Sigma-Aldrich

3-Indoleacetonitrile

98%

Synonym(s):

(3-Indolyl)acetonitrile, 3-(Cyanomethyl)indole, IAN, Indolylacetonitrile, NSC 523272

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About This Item

Empirical Formula (Hill Notation):
C10H8N2
CAS Number:
771-51-7
Molecular Weight:
156.18
Beilstein/REAXYS Number:
125488
EC Number:
212-232-1
MDL number:
MFCD00005628
UNSPSC Code:
12352100
PubChem Substance ID:
24847904
NACRES:
NA.22

assay

98%

form

solid

bp

157-160 °C/0.2 mmHg (lit.)

mp

33-36 °C (lit.)

SMILES string

N#CCc1c[nH]c2ccccc12

InChI

1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2

InChI key

DMCPFOBLJMLSNX-UHFFFAOYSA-N

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General description

3-Indoleacetonitrile (Indolylacetonitrile) is a light-induced auxin-inhibitory substance that is isolated from light-grown cabbage (Brassica olearea L.) shoots. It inhibits the biofilm formation of both E. coli O157:H7 and P. aeruginosa without affecting its growth.

Application

Reactant for preparation of:
  • Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Histone deacetylase inhibitors
  • Potential kinase inhibitors
  • Kv7/KCNQ potassium channel activators
  • Kinesin-Specific MKLP-2 Inhibitor
  • Pesticides
  • Potential PET cancer imaging agents
  • Agonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatment
  • Butyrylcholinesterase inhibitors
  • Necroptosis inhibitors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

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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Light-induced auxin-inhibiting substance from cabbage (Brassica oleacea L.) shoots.
Kosemura S, et al.
Tetrahedron Letters, 38(48), 8327-8330 (1997)
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Journal of environmental sciences (China), 58, 231-238 (2017-08-05)
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Science (New York, N.Y.), 323(5910), 95-101 (2008-12-20)
The perception of pathogen or microbe-associated molecular pattern molecules by plants triggers a basal defense response analogous to animal innate immunity and is defined partly by the deposition of the glucan polymer callose at the cell wall at the site
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