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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.)

functional group

nitrile

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)
Pedro Robles et al.
Plant physiology, 152(3), 1357-1372 (2010-01-02)
To identify genes involved in vascular patterning in Arabidopsis (Arabidopsis thaliana), we screened for abnormal venation patterns in a large collection of leaf shape mutants isolated in our laboratory. The rotunda1-1 (ron1-1) mutant, initially isolated because of its rounded leaves
Alexandra Kutz et al.
The Plant journal : for cell and molecular biology, 30(1), 95-106 (2002-04-23)
Arabidopsis thaliana expresses four nitrilases, three of which (NIT1, NIT2 and NIT3) are able to convert indole-3-acetonitrile to indole-3-acetic acid (IAA), the plant growth hormone, while the isozyme NIT4 is a beta-cyano-l-alanine hydratase/nitrilase. NIT3 promoter activity is marginal in leaves
Martin de Vos et al.
Plant physiology, 146(3), 916-926 (2008-01-15)
Like many crucifer-specialist herbivores, Pieris rapae uses the presence of glucosinolates as a signal for oviposition and larval feeding. Arabidopsis thaliana glucosinolate-related mutants provide a unique resource for studying the in vivo role of these compounds in affecting P. rapae
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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