indole-3-carboxaldehyde
Identification
| Name | indole-3-carboxaldehyde |
| IUPAC | 1H-indole-3-carbaldehyde |
| CAS Number | 487-89-8 |
| EINECS | 207-665-8 |
| FDA UNII | 7FN04C32UO |
| Molecular Formula | C9 H7 N O |
| Molecular Weight | 145.16099000 |
| MDL Number | MFCD00005622 |
| Nikkaji Number | J26.057F |
| Beilstein | 0114117 |
| XlogP3 | 1.70 (est) |
Regulatory
Physical Properties
| Food Chemicals Codex Listed | No |
| Melting Point | 196.50 °C. @ 760.00 mm Hg |
| Boiling Point | 339.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 332.00 °F. TCC ( 166.80 °C. ) (est) |
| logP (o/w) | 1.680 |
| Soluble in | water, 2927 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LDLo 600 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"\nBEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)\nBEHAVIORAL: ANTICONVULSANT']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
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Potential Uses
Natural Occurrence
Synonyms
3-
formylindole
indole-3-aldehyde
indole-3-carbaldehyde
1H-
indole-3-carbaldehyde
1H-
indole-3-carboxaldehyde
beta-
indolyl aldehyde
beta-
indolylaldehyde
PubMed:
A new oxathiolane from Enterobacter cloacae.
PubMed:
[Chemical constituents from ethyl acetate extract of flower of Albizia julibrissin].
PubMed:
[Chemical constituents from seeds of Brassica campestris].
PubMed:
Antioxidative properties of ascorbigen in using multiple antioxidant assays.
PubMed:
Indolylmethylene benzo[h]thiazolo[2,3-b]quinazolinones: synthesis, characterization and evaluation of anticancer and antimicrobial activities.
PubMed:
1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde.
PubMed:
[A new indole alkaloid from the stems of Brucea mollis].
PubMed:
The Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis.
PubMed:
Highly selective probe detects Cu2+ and endogenous NO gas in living cell.
PubMed:
Synthesis of Dynole 34-2, Dynole 2-24 and Dyngo 4a for investigating dynamin GTPase.
PubMed:
Synthesis of β-carboline-benzimidazole conjugates using lanthanum nitrate as a catalyst and their biological evaluation.
PubMed:
Aniline is an inducer, and not a precursor, for indole derivatives in Rubrivivax benzoatilyticus JA2.
PubMed:
Synthesis, molecular and crystal structure analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT investigation of its rotational conformers.
PubMed:
Targeting novel chemical and constitutive primed metabolites against Plectosphaerella cucumerina.
PubMed:
Alkaloids from the mangrove-derived actinomycete Jishengella endophytica 161111.
PubMed:
Indole conjugated silica and magnetic nanoparticles as inhibitors of HIF.
PubMed:
A turn-on indole-based sensor for hydrogen sulfate ion.
PubMed:
Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes.
PubMed:
Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones.
PubMed:
The synthesis and anticancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin.
PubMed:
Tryptophan catabolites from microbiota engage aryl hydrocarbon receptor and balance mucosal reactivity via interleukin-22.
PubMed:
Antimicrobial, crown gall tumor inhibitory and cytotoxicity assays of N-[(1-methyl-1H-indole-3-yl)methylene]amines synthesized by an improved protocol.
PubMed:
Expression of Pisum sativum PsAO3 gene, which encodes an aldehyde oxidase utilizing abscisic aldehyde, is induced under progressively but not rapidly imposed drought stress.
PubMed:
Seborrheic dermatitis: etiology, risk factors, and treatments: facts and controversies.
PubMed:
White light generation by carbonyl based indole derivatives due to proton transfer: an efficient fluorescence sensor.
PubMed:
1-(4-{2-[(E)-3-(4-Chloro-phen-yl)-3-oxo-prop-1-en-1-yl]phen-oxy}but-yl)-1H-indole-3-carbaldehyde.
PubMed:
Molecular structural, non-linear optical, second order perturbation and Fukui studies of Indole-3-Aldehyde using density functional calculations.
PubMed:
A family of indoles regulate virulence and Shiga toxin production in pathogenic E. coli.
PubMed:
Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions.
PubMed:
Anti-inflammatory and antimicrobial activity of 4,5-dihydropyrimidine-5-carbonitrile derivatives: their synthesis and spectral elucidation.
PubMed:
1H-Indole-3-carbaldehyde.
PubMed:
5-Methyl-1H-indole-3-carbaldehyde.
PubMed:
A new sesquiterpene from an endophytic Aspergillus versicolor strain.
PubMed:
Isolation and identification of secondary metabolites of Clitocybe nuda responsible for inhibition of zoospore germination of Phytophthora capsici.
PubMed:
1-(2-Methyl-benz-yl)-1H-indole-3-carbaldehyde.
PubMed:
Synthesis and characterization of some new complexes of Cu(II), Ni(II) and V(IV) with Schiff base derived from indole-3-carboxaldehyde. Biological activity on prokaryotes and eukaryotes.
PubMed:
Update of spectroscopic data for 4-hydroxydictyolactone and dictyol E isolated from a Halimeda stuposa - Dictyota sp. assemblage.
PubMed:
Synthesis of 5-alkylated barbituric acids and 3-alkylated indoles via microwave-assisted three-component reactions in solvent-free conditions using Hantzsch 1,4-dihydropyridines as reducing agents.
PubMed:
Conjugation of a 3-(1H-phenanthro[9,10-d]imidazol-2-yl)-1H-indole intercalator to a triplex oligonucleotide and to a three-way junction.
PubMed:
Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents.
PubMed:
2-Methyl-1-phenyl-sulfonyl-1H-indole-3-carbaldehyde.
PubMed:
Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation.
PubMed:
Trichoderma-induced plant immunity likely involves both hormonal- and camalexin-dependent mechanisms in Arabidopsis thaliana and confers resistance against necrotrophic fungi Botrytis cinerea.
PubMed:
Interaction of cruciferous phytoanticipins with plant fungal pathogens: indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are.
PubMed:
The activity pattern and gene expression profile of aldehyde oxidase during the development of Pisum sativum seeds.
PubMed:
A new cytotoxic indole-3-ethenamide from the halotolerant fungus Aspergillus sclerotiorum PT06-1.
PubMed:
Motile zoospores of Batrachochytrium dendrobatidis move away from antifungal metabolites produced by amphibian skin bacteria.
PubMed:
LC-MS/MS quantification of sulforaphane and indole-3-carbinol metabolites in human plasma and urine after dietary intake of selenium-fortified broccoli.
PubMed:
The Arabidopsis phi class glutathione transferase AtGSTF2: binding and regulation by biologically active heterocyclic ligands.
PubMed:
[Approaches to raising efficacy of treatment of patients with chronic prostatitis associated with intracellular infections].
PubMed:
Brassinin oxidase mediated transformation of the phytoalexin brassinin: structure of the elusive co-product, deuterium isotope effect and stereoselectivity.
PubMed:
The synthesis and spectral properties of a stimuli-responsive D-Ï-A charge transfer dye.
PubMed:
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
PubMed:
Production of indole-3-acetic acid and related indole derivatives from L-tryptophan by Rubrivivax benzoatilyticus JA2.
PubMed:
Aniline-induced tryptophan production and identification of indole derivatives from three purple bacteria.
PubMed:
Electrochemical behavior of indole-3-carboxaldehyde izonicotinoyl hydrazones: discussion on possible biological behavior.
PubMed:
Synthesis, Antiinflammatory and Antibacterial Activity of Novel Indolyl-isoxazoles.
PubMed:
Secondary metabolites of Volvariella bombycina and their inhibitory effects on melanogenesis.
PubMed:
2-Hy-droxy-5-[(E)-(1H-indol-3-yl-methyl-idene)aza-nium-yl]benzoate.
PubMed:
Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives.
PubMed:
Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer.
PubMed:
A chromanone alkaloid from Derris ovalifolia stem.
PubMed:
An efficient one-step synthesis of heterobiaryl pyrazolo[3,4-b]pyridines via indole ring opening.
PubMed:
Discovery of novel antileishmanial agents in an attempt to synthesize pentamidine-aplysinopsin hybrid molecule.
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:
Four new compounds from Paeonia albiflora.
PubMed:
Synthesis and assessment of 99mTc chelate-conjugated alendronate for development of specific radiopharmaceuticals.
PubMed:
Interruption of RNA processing machinery by a small compound, 1-[(4-chlorophenyl)methyl]-1H-indole-3-carboxaldehyde (oncrasin-1).
PubMed:
A combined experimental and theoretical study of the polar [3 + 2] cycloaddition of electrophilically activated carbonyl ylides with aldehydes and imines.
PubMed:
Iotrochotamides I and II: new ceramides from the Indonesian sponge Iotrochota purpurea.
PubMed:
Investigation of antimicrobial activities of indole-3-aldehyde hydrazide/hydrazone derivatives.
PubMed:
Amphibian chemical defense: antifungal metabolites of the microsymbiont Janthinobacterium lividum on the salamander Plethodon cinereus.
PubMed:
Antibacterial and Antifungal Studies on Some Schiff Base Complexes of Zinc(II).
PubMed:
Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents.
PubMed:
New Pd(II) complexes of the synthesized 1-N-substituted thiosemicarbazones of 3-indole carboxaldehyde: characterization and antiamoebic assessment against E. histolytica.
PubMed:
AhR ligands, malassezin, and indolo[3,2-b]carbazole are selectively produced by Malassezia furfur strains isolated from seborrheic dermatitis.
PubMed:
1-Vinyl-1H-indole-3-carbaldehyde.
PubMed:
trans-Bis(1H-indole-3-carbaldehyde thio-semicarbazonato-κN,S)nickel(II).
PubMed:
1H-Indole-3-carbaldehyde thio-semi-carbazone.
PubMed:
5-Bromo-1H-indole-3-carbaldehyde thio-semicarbazone.
PubMed:
1H-Indole-3-carbaldehyde azine.
PubMed:
Compounds from Wedelia chinensis synergistically suppress androgen activity and growth in prostate cancer cells.
PubMed:
[Chemical constituents from aerial parts of Plumbago zeylanica Linn].
PubMed:
Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde.
PubMed:
Synthesis, characterization and antiamoebic activity of new indole-3-carboxaldehyde thiosemicarbazones and their Pd(II) complexes.
PubMed:
Amorphane sesquiterpenes from a marine Streptomyces sp.
PubMed:
Synthesis and novel fluorescence phenomenon of terbium complex with a new Schiff base ligand derived from condensation of triaminotriethylamine and 3-indolemethanal.
PubMed:
Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin.
PubMed:
Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives.
PubMed:
Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: inhibitory activity against fungi and bacteria.
PubMed:
Characterization of the oxidase activity in mammalian catalase.
PubMed:
Isolation of three new naturally occurring compounds from the culture of Micromonospora sp. P1068.
PubMed:
Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases.
PubMed:
Aldehyde oxidase (AO) in the root nodules of Lupinus albus and Medicago truncatula: identification of AO in meristematic and infection zones.
PubMed:
Hymeniacidon perleve associated bioactive bacterium pseudomonas sp. NJ6-3-1.
PubMed:
(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile.
PubMed:
[Synthesis of 1-indole substituted beta-carboline alkaloid and its derivatives and evaluation of their preliminary antitumor activities].
PubMed:
Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice.
PubMed:
Universally occurring phenylpropanoid and species-specific indolic metabolites in infected and uninfected Arabidopsis thaliana roots and leaves.
PubMed:
Alkaloids from the fungus Lactarius subplinthogalus.
PubMed:
Complete and remarkable reversal of chemoselectivity in [4 + 2] cycloadditions involving electron-poor indoles as dienophiles. Diels-Alder versus hetero-Diels-Alder processes.
PubMed:
Synthesis of annulated gamma-carbolines and heteropolycycles by the palladium-catalyzed intramolecular annulation of alkynes.
PubMed:
Three new jatrophane-type diterpenes from Euphorbia pubescens.
PubMed:
Antimalarial agents from plants. III. Trichothecenes from Ficus fistulosa and Rhaphidophora decursiva.
PubMed:
Isolation and identification of lateral bud growth inhibitor, indole-3-aldehyde, involved in apical dominance of pea seedlings.
PubMed:
Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea.
PubMed:
Peroxynitrite scavenging activities of aromatic compounds isolated from Konnyaku, Amorphophallus konjac K.Koch.
PubMed:
1,2-bis(1H-indol-3-yl)ethane-1,2-dione, an indole alkaloid from the marine sponge Smenospongia sp.
PubMed:
Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip.
PubMed:
An efficient synthesis of 4-(phenylsulfonyl)-4H-furo[3,4-b]indoles.
PubMed:
Fate of indole-3-carbinol in cultured human breast tumor cells.
PubMed:
Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.
PubMed:
Structure-activity relationship for bromoindole carbaldehydes: effects on the sea urchin embryo cell cycle.
PubMed:
Metabolism of tyrosine and tryptophan--new genes for old pathways.
PubMed:
Participation of the photosensitizer alpha-terthienyl in the peroxidase-catalyzed oxidation of indole-3-acetic acid.
PubMed:
[Development of synthetic methods for 4-substituted indoles and their applications for the syntheses of natural products].
PubMed:
Functional expression of two Arabidopsis aldehyde oxidases in the yeast Pichia pastoris.
PubMed:
Determination of monoamine oxidase activity by HPLC with fluorimetric detection.
PubMed:
Identification of skatolyl hydroperoxide and its role in the peroxidase-catalysed oxidation of indol-3-yl acetic acid.
PubMed:
Higher activity of an aldehyde oxidase in the auxin-overproducing superroot1 mutant of Arabidopsis thaliana.
PubMed:
Indolyl nicotinic hydrazides and their neurological studies.
PubMed:
New indole derivatives with free radical scavenging activity from Agrocybe cylindracea.
PubMed:
Metabolism studies of indole derivatives using a staurosporine producer, Streptomyces staurosporeus.
PubMed:
Indole-3-carbinol as a scavenger of free radicals.
PubMed:
Purification and Properties of Flavin- and Molybdenum-Containing Aldehyde Oxidase from Coleoptiles of Maize.
PubMed:
Studies on the synthesis and structure-activity relationships of 5-(3'-indolal)-2-thiohydantoin derivatives as aldose reductase enzyme inhibitors.
PubMed:
Spectroscopic studies of cutaneous photosensitizing agents. XVIII. Indomethacin.
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:
Mutagen formation on nitrite treatment of indole compounds derived from indole-glucosinolate.
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:
Different lethal effects by enzyme-generated triplet indole-3-aldehyde in different Escherichia coli strains.
PubMed:
Indoles in edible members of the Cruciferae.
PubMed:
Identification of minor nitrosation products of the alkaloid gramine by mass spectrometry.
PubMed:
Auxin production by plant-pathogenic pseudomonads and xanthomonads.
PubMed:
Endogenous indoles and the biosynthesis and metabolism of indole-3-acetic acid in cultures of Rhizobium phaseoli.
PubMed:
Structure-activity relationships of dietary indoles: a proposed mechanism of action as modifiers of xenobiotic metabolism.
PubMed:
4-Methoxyindole derivatives as nitrosable precursors of mutagens in Chinese cabbage.
PubMed:
Activation of urocanase from Pseudomonas putida by electronically excited triplet species.
PubMed:
The effect of indole-3-carbinol, an aflatoxin B1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout hepatic mixed function oxidase system.
PubMed:
Effects of enzyme/substrate ratio and of cofactors on the oxidation products of indole-3-acetic acid catalyzed by peroxidase.
PubMed:
The metabolism of tryptophan and 7-chlorotryptophan in Pseudomonas pyrrocinia and Pseudomonas aureofaciens.
PubMed:
Peroxidase-generated triplet indole-3-aldehyde adds to uridine bases and excites the 4-thiouridine group in t-RNAPhe.
PubMed:
Metabolism of Tryptophan, Indole-3-acetic Acid, and Related Compounds in Parasitic Plants from the Genus Orobanche.
PubMed:
Antiviral compounds. XVII - Synthesis and in vitro antiviral activity of 1-substituted 2-chloro- and 2-methoxyindole-3-carboxaldehyde thiosemicarbazones.
PubMed:
Excited indole-3-aldehyde from the peroxidase-catalyzed aerobic oxidation of indole-3-acetic acid. Reaction with and energy transfer to transfer ribonucleic acid.
PubMed:
Tryptophan side chain oxidase from Pseudomonas. Oxidation of skatole to indole-3-carboxaldehyde via indole-3-methanol.
PubMed:
Purification of indolyl-3-alkane alpha-hydroxylase by affinity chromatography on indolyl-agarose columns.
PubMed:
New indolic hypotensive agents.
PubMed:
Inactivity of Oxidation Products of Indole-3-acetic Acid on Ethylene Production in Mung Bean Hypocotyls.
PubMed:
Cucumber seedling indoleacetaldehyde oxidase.
PubMed:
Antibiotic metabolites from a marine pseudomonad.
PubMed:
Indolic tryptophan metabolism in uraemia.
PubMed:
Identification of plant hormones from cotton ovules.
PubMed:
Isolation and identification of indole-3-carboxaldehyde: a major new urinary metabolite of D-tryptophan.
PubMed:
[Transport of [(14)C] auxin from young pods of Vicia faba L].
PubMed:
Indole-3-methanol-a metabolite of indole-3-acetic acid in pea seedlings.
PubMed:
Peroxidase-catalyzed formation of indole-3-carbaldehyde and 4-hydroxyquinoline from indole-3-acetaldehyde.
PubMed:
The transport and metabolism of (14)C-labelled indoleacetic acid in intact pea seedlings.
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:
3-Methyleneoxindole reductase of peas.
PubMed:
[Occurrence and metabolism of auxin in multicellular algae of the Baltic sea].
PubMed:
[Studies on chemotherapeutics for Mycobacterium tuberculosis. XVII. Synthesis and antibacterial activity on Mycobacterium tuberculosis of indole-3-carboxaldehyde derivatives].
PubMed:
[The degradation of tryptophan in Endomycopsis Vernalis and other yeasts].
PubMed:
ISOLATION OF 2-PHENYLACETAMIDE, INDOLE-3-ACETAMIDE, AND INDOLE-3-CARBOXALDEHYDE FROM ETIOLATED SEEDLING OF PHASEOLUS.
PubMed:
Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid.
PubMed:
Formation of indole-3-aldehyde by indoleacetic oxidase.
PubMed:
The synthesis of indole-3-aldehyde and its homologues.