129453
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:
Molecular Weight:
156.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-232-1
Beilstein/REAXYS Number:
125488
MDL number:
Assay:
98%
Form:
solid
InChI key
DMCPFOBLJMLSNX-UHFFFAOYSA-N
InChI
1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
SMILES string
N#CCc1c[nH]c2ccccc12
assay
98%
form
solid
bp
157-160 °C/0.2 mmHg (lit.)
Quality Level
functional group
nitrile
Related Categories
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
flash_point_f
233.6 °F - closed cup
flash_point_c
112 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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
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
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
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