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129453 Aldrich

3-Indoleacetonitrile

98%

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

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Properties

Related Categories Building Blocks, C10, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   98%
bp   157-160 °C/0.2 mmHg(lit.)
mp   33-36 °C(lit.)

Description

Packaging

5, 25 g in glass bottle

Application

Reactant for preparation of:
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1
• Histone deacetylase inhibitors2
• Potential kinase inhibitors3
• Kv7/KCNQ potassium channel activators4
• Kinesin-Specific MKLP-2 Inhibitor5
• Pesticides6
• Potential PET cancer imaging agents7
• Agonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatment8
• Butyrylcholinesterase inhibitors9
• Necroptosis inhibitors10

General description

3-Indoleacetonitrile (Indolylacetonitrile) is a light-induced auxin-inhibitory substance that is isolated from light-grown cabbage (Brassica olearea L.) shoots11. It inhibits the biofilm formation of both E. coli O157:H7 and P. aeruginosa without affecting its growth12.

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Palau’Chlor

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
36/37
WGK Germany 
3
RTECS 
AM0700000
Flash Point(F) 
233.6 °F
Flash Point(C) 
112 °C

Protocols & Articles

Related Content

Indoles, Purines, and Their Isosteres

Substituted indoles and purines have frequently been referred to as “privileged structures” since they are capable of binding to multiple receptors with high affinity, and thus have applications acro...
Keywords: Applications, Building blocks, Medicinal chemistry

Peer-Reviewed Papers

References

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1. Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Dolusic, E.; et al. J. Med. Chem. 54, 5320, (2011)

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2. Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors. Shultz, M., D.; et al. J. Med. Chem. 54, 4752, (2011)

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3. Pierce, L. T.; et al. Tetrahedron 67, 4601, (2011)

4. Design, synthesis and biological activity of pyrazolo[1,5-a]pyrimidin-7(4H)-ones as novel Kv7/KCNQ potassium channel activators. Qi, J.; et al. Eur. J. Med. Chem. 46, 934, (2011)

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5. Relocation of Aurora B and survivin from centromeres to the central spindle impaired by a kinesin-specific MKLP-2 inhibitor. Tcherniuk, S.; et al. Angew. Chem. Int. Ed. Engl. 49, 8228, (2010)

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6. A short formal total synthesis of strychnine with a samarium diiodide induced cascade reaction as the key step. Beemelmanns, C.; Reissig, H.-U. Angew. Chem. Int. Ed. Engl. 49, 8021, (2010)

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7. The first design and synthesis of [11C]MKC-1 ([11C]Ro 31-7453), a new potential PET cancer imaging agent. Wang, M.; et al. Nucl. Med. Biol. 37, 763, (2010)

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8. Discovery of XL335 (WAY-362450), a highly potent, selective, and orally active agonist of the farnesoid X receptor (FXR). Flatt, B.; et al. J. Med. Chem. 52, 904, (2009)

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9. Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors. Rivera-Becerril, E.; et al. J. Med. Chem. 51, 5271, (2008)

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10. Structure-activity relationship study of novel necroptosis inhibitors. Teng, X.; et al. Bioorg. Med. Chem. Lett. 15, 5039, (2005)

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11. Light-induced auxin-inhibiting substance from cabbage (Brassica oleacea L.) shoots. Kosemura S, et al. Tetrahedron Lett. 38(48), 8327-8330, (1997)

12. 3-indolylacetonitrile decreases Escherichia coli O157:H7 biofilm formation and Pseudomonas aeruginosa virulence. Lee JH, Cho MH, Lee J. Environ. Microbiol. 13, 62-73, (2011)

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Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Nafisi M, Goregaoker S, Botanga CJ, et al. Plant Cell 19(6), 2039-52, (2007)

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Indole-3-acetonitrile production from indole glucosinolates deters oviposition by Pieris rapae. de Vos M, Kriksunov KL, and Jander G Plant Physiol. 146(3), 916-26, (2008)

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The RON1/FRY1/SAL1 gene is required for leaf morphogenesis and venation patterning in Arabidopsis. Robles P, Fleury D, Candela H, et al. Plant Physiol. 152(3), 1357-72, (2010)

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Novel tryptophan metabolism by a potential gene cluster that is widely distributed among actinomycetes. Ozaki T, Nishiyama M, and Kuzuyama T J. Biol. Chem. 288(14), 9946-56, (2013)

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Effect of boiling on the content of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage. Ciska E, Verkerk R, and Honke J J. Agric. Food Chem. 57(6), 2334-8, (2009)

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Redirection of tryptophan metabolism in tobacco by ectopic expression of an Arabidopsis indolic glucosinolate biosynthetic gene. Nonhebel H, Yuan Y, Al-Amier H, et al. Phytochemistry 72(1), 37-48, (2011)

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ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis. Burow M, Zhang ZY, Ober JA, et al. Phytochemistry 69(3), 663-71, (2008)

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The bacterial signalling molecule indole attenuates the virulence of the fungal pathogen Candida albicans. Oh S, Go GW, Mylonakis E, et al. J. Appl. Microbiol. 113(3), 622-8, (2012)

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Pseudomonas syringae pv. syringae B728a hydrolyses indole-3-acetonitrile to the plant hormone indole-3-acetic acid. Howden AJ, Rico A, Mentlak T, et al. Mol. Plant Pathol. 10(6), 857-65, (2009)

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A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana. Kutz A, Müller A, Hennig P, et al. Plant J. 30(1), 95-106, (2002)

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Comprehensive feature analysis for sample classification with comprehensive two-dimensional LC. Reichenbach SE, Tian X, Tao Q, et al. J. Sep. Sci. 33(10), 1365-74, (2010)

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Glucosinolate metabolites required for an Arabidopsis innate immune response. Clay NK, Adio AM, Denoux C, et al. Science 323(5910), 95-101, (2009)

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Arabidopsis mutants resistant to the auxin effects of indole-3-acetonitrile are defective in the nitrilase encoded by the NIT1 gene. Normanly J, Grisafi P, Fink GR, et al. Plant Cell 9(10), 1781-90, (1997)

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The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana. Böttcher C, Westphal L, Schmotz C, et al. Plant Cell 21(6), 1830-45, (2009)

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Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana. Su T, Xu J, Li Y, et al. Plant Cell 23(1), 364-80, (2011)

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Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis. Sugawara S, Hishiyama S, Jikumaru Y, et al. Proc. Natl. Acad. Sci. U. S. A. 106(13), 5430-5, (2009)

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The Nitrilase ZmNIT2 converts indole-3-acetonitrile to indole-3-acetic acid. Park WJ, Kriechbaumer V, Möller A, et al. Plant Physiol. 133(2), 794-802, (2003)

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Indole-3-acetic acid is synthesized from L-tryptophan in roots of Arabidopsis thaliana. Müller A, Hillebrand H, and Weiler EW Planta 206(3), 362-9, (1998)

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Maize nitrilases have a dual role in auxin homeostasis and beta-cyanoalanine hydrolysis. Kriechbaumer V, Park WJ, Piotrowski M, et al. J. Exp. Bot. 58(15-16), 4225-33, (2007)

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Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Pedras MS, Nycholat CM, Montaut S, et al. Phytochemistry 59(6), 611-25, (2002)

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Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices. Renwick AB, Mistry H, Barton PT, et al. Food Chem. Toxicol. 37(6), 609-18, (1999)

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ATAF2, a NAC transcription factor, binds to the promoter and regulates NIT2 gene expression involved in auxin biosynthesis. Huh SU, Lee SB, Kim HH, et al. Mol. Cells 34(3), 305-13, (2012)

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Effect of the pasteurization process on the contents of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage. Ciska E and Honke J J. Agric. Food Chem. 60(14), 3645-9, (2012)

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Phytotoxin production and phytoalexin elicitation by the phytopathogenic fungus Sclerotinia sclerotiorum. Pedras MS and Ahiahonu PW J. Chem. Ecol. 30(11), 2163-79, (2004)

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[Development of synthetic methods for 4-substituted indoles and their applications for the syntheses of natural products]. Yamada F Yakugaku Zasshi 120(4), 363-73, (2000)

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Beil. 22,V,3,74

Aldrich MSDS 1, 1088:C / Corp MSDS 1 (1), 1983:C / FT-IR 1 (2), 678:C / FT-IR 2 (3), 3609:C / FT-NMR 1 (3), 159:A / IR-Spectra (2), 1097:C / IR-Spectra (3), 1261:G / NMR-Reference 2 (2), 547:C / RegBook 1 (2), 2423:C / Sax 6, 1614 / Sigma FT-IR 1 (2), 656:B / Structure Index 1, 384:B:5

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