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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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

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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Light-induced auxin-inhibiting substance from cabbage (Brassica oleacea L.) shoots.
Kosemura S, et al.
Tetrahedron Letters, 38(48), 8327-8330 (1997)
Jin-Hyung Lee et al.
Environmental microbiology, 13(1), 62-73 (2010-07-24)
Intercellular signal indole and its derivative hydroxyindoles inhibit Escherichia coli biofilm and diminish Pseudomonas aeruginosa virulence. However, indole and bacterial indole derivatives are unstable in the microbial community because they are quickly degraded by diverse bacterial oxygenases. Hence, this work
Tongbing Su et al.
The Plant cell, 23(1), 364-380 (2011-01-18)
Camalexin, a major phytoalexin in Arabidopsis thaliana, consists of an indole ring and a thiazole ring. The indole ring is produced from Trp, which is converted to indole-3-acetonitrile (IAN) by CYP79B2/CYP79B3 and CYP71A13. Conversion of Cys(IAN) to dihydrocamalexic acid and
J Normanly et al.
The Plant cell, 9(10), 1781-1790 (1997-11-22)
Indole-3-acetonitrile (IAN) is a candidate precursor of the plant growth hormone indole-3-acetic acid (IAA). We demonstrated that IAN has auxinlike effects on Arabidopsis seedlings and that exogenous IAN is converted to IAA in vivo. We isolated mutants with reduced sensitivity
Nicole K Clay et al.
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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