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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Flash Point: | > 230.00 °F. TCC ( > 110.00 °C. )
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| Soluble in: |
| | water, 1587 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for 3-indolyl acetonitrile usage levels up to: | | | not for fragrance use.
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| Recommendation for 3-indolyl acetonitrile flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | acetonitrile, 3-indolyl- | | 2-(1H- | indol-3-yl)acetonitrile | | | indole-3-acetonitrile | | 1H- | indole-3-acetonitrile | | | indolylacetonitrile | | 3- | indolylacetonitrile |
Articles:
| PubMed:Response of the plant hormone network to boron deficiency. |
| PubMed:Characterization of a novel nitrilase, BGC4, from Paraburkholderia graminis showing wide-spectrum substrate specificity, a potential versatile biocatalyst for the degradation of nitriles. |
| PubMed:Development of a solid-phase extraction method with simple MEKC-UV analysis for simultaneous detection of indole metabolites in human urine after administration of indole dietary supplement. |
| PubMed:Multiresponse optimization of a UPLC method for the simultaneous determination of tryptophan and 15 tryptophan-derived compounds using a Box-Behnken design with a desirability function. |
| PubMed:Arabidopsis NITRILASE 1 Contributes to the Regulation of Root Growth and Development through Modulation of Auxin Biosynthesis in Seedlings. |
| PubMed:Synthesis and Antimicrobial Characterization of Half-Calycanthaceous Alkaloid Derivatives. |
| PubMed:Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects. |
| PubMed:Dynamic Precision Phenotyping Reveals Mechanism of Crop Tolerance to Root Herbivory. |
| PubMed:Arabidopsis Myrosinase Genes AtTGG4 and AtTGG5 Are Root-Tip Specific and Contribute to Auxin Biosynthesis and Root-Growth Regulation. |
| PubMed:Stability of glucosinolates and glucosinolate degradation products during storage of boiled white cabbage. |
| PubMed:Proteomic analyses of the interaction between the plant-growth promoting rhizobacterium Paenibacillus polymyxa E681 and Arabidopsis thaliana. |
| PubMed:The role of MYB34, MYB51 and MYB122 in the regulation of camalexin biosynthesis in Arabidopsis thaliana. |
| PubMed:Functional interpretation and structural insights of Arabidopsis lyrata cytochrome P450 CYP71A13 involved in auxin synthesis. |
| PubMed:Influence of fermentation on glucosinolates and glucobrassicin degradation products in sauerkraut. |
| PubMed:TRANSCRIPTION ACTIVATOR-LIKE EFFECTOR NUCLEASE-Mediated Generation and Metabolic Analysis of Camalexin-Deficient cyp71a12 cyp71a13 Double Knockout Lines. |
| PubMed:SEPARATION AND PURIFICATION OF TWO MINOR COMPOUNDS FROM RADIX ISATIDIS BY INTEGRATIVE MPLC AND HSCCC WITH PREPARATIVE HPLC. |
| PubMed:Classic myrosinase-dependent degradation of indole glucosinolate attenuates fumonisin B1-induced programmed cell death in Arabidopsis. |
| PubMed:Simultaneous detection and quantification of indole-3-acetic acid (IAA) and indole-3-butyric acid (IBA) produced by rhizobacteria from l-tryptophan (Trp) using HPTLC. |
| PubMed:Characterization of a nitrilase and a nitrile hydratase from Pseudomonas sp. strain UW4 that converts indole-3-acetonitrile to indole-3-acetic acid. |
| PubMed:The Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis. |
| PubMed:Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production. |
| PubMed:Could nitrile derivatives of turnip (Brassica rapa) glucosinolates be hepato- or cholangiotoxic in cattle? |
| PubMed:Indole-3-acetic acid in plant-microbe interactions. |
| PubMed:Minimum set of cytochromes P450 for reconstituting the biosynthesis of camalexin, a major Arabidopsis antibiotic. |
| PubMed:Foliar application of biofilm formation-inhibiting compounds enhances control of citrus canker caused by Xanthomonas citri subsp. citri. |
| PubMed:Novel tryptophan metabolism by a potential gene cluster that is widely distributed among actinomycetes. |
| PubMed:A simple method for simultaneous RP-HPLC determination of indolic compounds related to bacterial biosynthesis of indole-3-acetic acid. |
| PubMed:ATAF2, a NAC transcription factor, binds to the promoter and regulates NIT2 gene expression involved in auxin biosynthesis. |
| PubMed:The bacterial signalling molecule indole attenuates the virulence of the fungal pathogen Candida albicans. |
| PubMed:Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside. Proposal for structural revision of the natural product. |
| PubMed:Arabidopsis acetyl-amido synthetase GH3.5 involvement in camalexin biosynthesis through conjugation of indole-3-carboxylic acid and cysteine and upregulation of camalexin biosynthesis genes. |
| PubMed:Effect of the pasteurization process on the contents of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage. |
| PubMed:Indole and 3-indolylacetonitrile inhibit spore maturation in Paenibacillus alvei. |
| PubMed:Induction of glandular stomach cancers in Helicobacter pylori-infected Mongolian gerbils by 1-nitrosoindole-3-acetonitrile. |
| PubMed:Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana. |
| PubMed:Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential. |
| PubMed:Redirection of tryptophan metabolism in tobacco by ectopic expression of an Arabidopsis indolic glucosinolate biosynthetic gene. |
| PubMed:Production of indole-3-acetic acid and related indole derivatives from L-tryptophan by Rubrivivax benzoatilyticus JA2. |
| PubMed:Novel indole C-glycosides from Isatis indigotica and their potential cytotoxic activity. |
| PubMed:3-indolylacetonitrile decreases Escherichia coli O157:H7 biofilm formation and Pseudomonas aeruginosa virulence. |
| PubMed:Comprehensive feature analysis for sample classification with comprehensive two-dimensional LC. |
| PubMed:The RON1/FRY1/SAL1 gene is required for leaf morphogenesis and venation patterning in Arabidopsis. |
| PubMed:Pseudomonas syringae pv. syringae B728a hydrolyses indole-3-acetonitrile to the plant hormone indole-3-acetic acid. |
| PubMed:Auxin biosynthesis in pea: characterization of the tryptamine pathway. |
| PubMed:The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana. |
| PubMed:Evolution of camalexin and structurally related indolic compounds. |
| PubMed:Effect of boiling on the content of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage. |
| PubMed:The antimicrobial effects of glucosinolates and their respective enzymatic hydrolysis products on bacteria isolated from the human intestinal tract. |
| PubMed:Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis. |
| PubMed:Glucosinolate metabolites required for an Arabidopsis innate immune response. |
| PubMed:Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes. |
| PubMed:Primary or secondary? Versatile nitrilases in plant metabolism. |
| PubMed:Indole-3-acetonitrile production from indole glucosinolates deters oviposition by Pieris rapae. |
| PubMed:Maize nitrilases have a dual role in auxin homeostasis and beta-cyanoalanine hydrolysis. |
| PubMed:ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis. |
| PubMed:Molecular cloning of Brassica rapa nitrilases and their expression during clubroot development. |
| PubMed:Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. |
| PubMed:Evaluation of matrix effects in metabolite profiling based on capillary liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry. |
| PubMed:Auxin biosynthesis in maize. |
| PubMed:Phytotoxin production and phytoalexin elicitation by the phytopathogenic fungus Sclerotinia sclerotiorum. |
| PubMed:Partial purification of an enzyme hydrolyzing indole-3-acetamide from rice cells. |
| PubMed:The Nitrilase ZmNIT2 converts indole-3-acetonitrile to indole-3-acetic acid. |
| PubMed:Cloning of a nitrilase gene from the cyanobacterium Synechocystis sp. strain PCC6803 and heterologous expression and characterization of the encoded protein. |
| PubMed:Probing crucial metabolic pathways in fungal pathogens of crucifers: biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites. |
| PubMed:[Research of indole-3-acetic acid biosynthetic pathway of Klebsiella oxytoca SG-11 by HPLC and GC-MS]. |
| PubMed:Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. |
| PubMed:Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana. |
| PubMed:A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana. |
| PubMed:Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. |
| PubMed:Characterization and synthetic applications of recombinant AtNIT1 from Arabidopsis thaliana. |
| PubMed:Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster. |
| PubMed:Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. |
| PubMed:Indolic constituents and indole-3-acetic acid biosynthesis in the wild-type and a tryptophan auxotroph mutant of Arabidopsis thaliana. |
| PubMed:Physiological evidence for differently regulated tryptophan-dependent pathways for indole-3-acetic acid synthesis in Azospirillum brasilense. |
| PubMed:Genes encoding nitrilase-like proteins from tobacco. |
| PubMed:IAA-synthase, an enzyme complex from Arabidopsis thaliana catalyzing the formation of indole-3-acetic acid from (S)-tryptophan. |
| PubMed:[Development of synthetic methods for 4-substituted indoles and their applications for the syntheses of natural products]. |
| PubMed:Specific enzymatic chlorination of tryptophan and tryptophan derivatives. |
| PubMed:Structural analysis of the TNIT4 genes encoding nitrilase-like protein from tobacco. |
| PubMed:Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices. |
| PubMed:Indole glucosinolate and auxin biosynthesis in Arabidopsis thaliana (L.) Heynh. glucosinolate mutants and the development of clubroot disease. |
| PubMed:Biosynthesis of indole-3-acetic acid in Azospirillum brasilense. Insights from quantum chemistry. |
| PubMed:Indole-3-acetic acid is synthesized from L-tryptophan in roots of Arabidopsis thaliana. |
| PubMed:Arabidopsis mutants resistant to the auxin effects of indole-3-acetonitrile are defective in the nitrilase encoded by the NIT1 gene. |
| PubMed:Quantification of free plus conjugated indoleacetic acid in arabidopsis requires correction for the nonenzymatic conversion of indolic nitriles. |
| PubMed:Structure of the gene encoding nitrilase 1 from Arabidopsis thaliana. |
| PubMed:Transgenic tobacco plants expressing the Arabidopsis thaliana nitrilase II enzyme. |
| PubMed:3-Methylindole (skatole) and indole production by mixed populations of pig fecal bacteria. |
| PubMed:Occurrence of enzymes involved in biosynthesis of indole-3-acetic acid from indole-3-acetonitrile in plant-associated bacteria, Agrobacterium and Rhizobium. |
| PubMed:Differential regulation of an auxin-producing nitrilase gene family in Arabidopsis thaliana. |
| PubMed:Molecular characterization of two cloned nitrilases from Arabidopsis thaliana: key enzymes in biosynthesis of the plant hormone indole-3-acetic acid. |
| PubMed:Insecticidal and fungicidal compounds from Isatis tinctoria. |
| PubMed:Nitrilase in biosynthesis of the plant hormone indole-3-acetic acid from indole-3-acetonitrile: cloning of the Alcaligenes gene and site-directed mutagenesis of cysteine residues. |
| PubMed:Effects of indole-3-carbinol on biotransformation enzymes in the rat: in vivo changes in liver and small intestinal mucosa in comparison with primary hepatocyte cultures. |
| PubMed:Cloning and expression of an Arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid. |
| PubMed:In-vitro testing and the carcinogenic potential of several nitrosated indole compounds. |
| PubMed:Mutagen formation on nitrite treatment of indole compounds derived from indole-glucosinolate. |
| PubMed:Stability of mutagenic nitrosated products of indole compounds occurring in vegetables. |
| PubMed:Several known indole compounds are not important precursors of direct mutagenic N-nitroso compounds in green cabbage. |
| PubMed:Induction of estradiol metabolism by dietary indole-3-carbinol in humans. |
| PubMed:The stability of the nitrosated products of indole, indole-3-acetonitrile, indole-3-carbinol and 4-chloroindole. |
| PubMed:Modulating effects of naturally occurring indoles on SCE induction depend largely on the type of mutagen. |
| PubMed:Modulating effects of indoles on benzo[a]pyrene-induced sister chromatid exchanges and the balance between drug-metabolizing enzymes. |
| PubMed:32P-postlabeling analysis of DNA adducts in rat stomach with 1-nitrosoindole-3-acetonitrile, a direct-acting mutagenic indole compound formed by nitrosation. |
| PubMed:Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species. |
| PubMed:Indoles in edible members of the Cruciferae. |
| PubMed:Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products. |
| PubMed:Microsomal oxidation of allelochemicals in generalist (Spodoptera frugiperda) and semispecialist (Anticarsia gemmatalis) insect. |
| PubMed:A co-cultivation system as a model for in vitro studies of modulating effects of naturally occurring indoles on the genotoxicity of model compounds. |
| PubMed:Recently identified nitrite-reactive compounds in food: occurrence and biological properties of the nitrosated products. |
| PubMed:Structure-activity relationships of dietary indoles: a proposed mechanism of action as modifiers of xenobiotic metabolism. |
| PubMed:A mutagen precursor in Chinese cabbage, indole-3-acetonitrile, which becomes mutagenic on nitrite treatment. |
| PubMed:T-DNA-encoded auxin formation in crown-gall cells. |
| PubMed:Nitrosatable precursors of mutagens in vegetables and soy sauce. |
| PubMed:Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives. |
| PubMed:Effects of dietary compounds on alpha-hydroxylation of N-nitrosopyrrolidine and N'-nitrosonornicotine in rat target tissues. |
| PubMed:Effect of micronutrients, antioxidants and related compounds on the mutagenicity of 3,2'-dimethyl-4-aminobiphenyl, a colon and breast carcinogen. |
| PubMed:Indole-3-carbinol and indole-3-acetonitrile influence on hepatic microsomal metabolism. |
| PubMed:Glutathione S-transferase activity: enhancement by compounds inhibiting chemical carcinogenesis and by dietary constituents. |
| PubMed:Inhibition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles. |
| PubMed:Dietary constituents altering the responses to chemical carcinogens. |
| PubMed:Effects of dietary constituents on the metabolism of chemical carcinogens. |
| PubMed:Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. |
| PubMed:Metabolism of indole-3-acetaldoxime in plants. |
| PubMed:[Studies on indole derivaties. XI. Reactions of 3-indolylacetonitrile derivatives with carbondisulfide]. |
| PubMed:The timing of growth promotion and conversion to indole-3-acetic acid for auxin precursors. |
| PubMed:Formation of 4-amino-3,5-di(3-indolylmethyl)-s-triazole from indole-3-acetonitrile and hydrazine. |
| PubMed:[Occurrence and metabolism of auxin in multicellular algae of the baltic sea : II. On the formation of Indoleacetic acid from tryptophan, with regard to the influence of the marine bacteria]. |
| PubMed:[Occurrence and metabolism of auxin in multicellular algae of the Baltic sea]. |
| PubMed:Uptake of Indole-3-acetic Acid and Indole-3-acetonitrile by Avena Coleoptile Sections. |
| PubMed:Growth Inhibition of Insects and a Fungus by Indole-3-Acetonitrile. |
| PubMed:Biogenesis of ascorbigen, 3-indolylacetonitrile and indole-3-carboxylic acid from D, L-tryptophan-3-14C in Brassica oleracea L. |
| PubMed:[Determination of indole bodies, especially indole-3-acetonitrile, by fluorescent analysis on paper chromatograms]. |
| PubMed:3-indolylacetonitrile: a naturally occurring plant growth hormone. |
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Myrosinase-induced hydrolysis product of indole glucosinolates, found in cabbage and other crucifers
3-Indoleacetonitrile is a phytoalexin. Phytoalexins are antibiotics produced by plants that are under attack. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids and alkaloids; a plant that has anti-insect phytoalexins may not have the ability to repel a fungal attack. 3-Indoleacetonitrile is common in cruciferous vegetables such as cabbage, cauliflower, broccoli, and Brussels sprouts. Dietary indoles in cruciferous vegetables induce cytochrome P450 enzymes and have prevented tumors in various animal models. Consumption of Brassica vegetables is associated with a reduced risk of cancer of the alimentary tract in animal models and human populations. (PMID: 15612779, 15884814, 2342128, 3014947, 3880668, 6334634, 6419397, 6426808, 6584878, 6725517, 6838646, 7123561); however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal. Phytoalexins produced in plants act as toxins to the attacking organism. They may puncture the cell wall, delay maturation, disrupt metabolism or prevent reproduction of the pathogen in question. However, phytoalexins are often targeted to specific predators
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3D/inchi