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129453

Sigma-Aldrich

3-Indoleacetonitrile

98%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C10H8N2
Numero CAS:
771-51-7
Peso molecolare:
156.18
Beilstein:
125488
Numero CE:
212-232-1
Numero MDL:
MFCD00005628
Codice UNSPSC:
12352100
ID PubChem:
24847904
NACRES:
NA.22

Saggio

98%

Forma fisica

solid

P. eboll.

157-160 °C/0.2 mmHg (lit.)

Punto di fusione

33-36 °C (lit.)

Stringa SMILE

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
DMCPFOBLJMLSNX-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

233.6 °F - closed cup

Punto d’infiammabilità (°C)

112 °C - closed cup

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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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
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
Yukako Komaki et al.
Journal of environmental sciences (China), 58, 231-238 (2017-08-05)
Disinfection by-products occur widely as the unintended effect of water disinfection and are associated with toxicity and adverse human health effects. Yet the molecular mechanisms of their toxicity are not well understood. To investigate the molecular basis of hyperploidy induction
Ewa Ciska et al.
Journal of agricultural and food chemistry, 57(6), 2334-2338 (2009-03-19)
The aim of the study was to investigate the effect of the boiling process on the content of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage. The cabbage was boiled for 5 to 60 min. Boiling resulted in a decrease
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