Home Indole and Oxindoles 83-34-1
83-34-1,MFCD00005627
Catalog No.:AA003JOR

83-34-1 | 3-Methylindole

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5g
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10g
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$16.00   $11.00
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25g
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003JOR
Chemical Name:
3-Methylindole
CAS Number:
83-34-1
Molecular Formula:
C9H9N
Molecular Weight:
131.1745
MDL Number:
MFCD00005627
SMILES:
Cc1c[nH]c2c1cccc2
NSC Number:
122024
FEMA Number:
3019
Properties
Properties
 
BP:
265-266°C at 760 mmHg  
Form:
Solid  
MP:
92-97 °C(lit.)  
Refractive Index:
1.6070 (estimate)  
Stability:
Light Sensitive  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
122  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Donor Count:
1  
XLogP3:
2.6  

Literature

Title: Activation of the aryl hydrocarbon receptor decreases rifampicin-induced CYP3A4 expression in primary human hepatocytes and HepaRG.

Journal: Toxicology letters 20170805

Title: Quantitative determination of the boar taint compounds androstenone, skatole, indole, 3α-androstenol and 3β-androstenol in wild boars (Sus scrofa) reveals extremely low levels of the tryptophan-related degradation products.

Journal: Food chemistry 20121215

Title: Predicting the likelihood of developing boar taint: early physical indicators in entire male pigs.

Journal: Meat science 20121201

Title: Consumer studies on sensory acceptability of boar taint: a review.

Journal: Meat science 20121201

Title: A single nucleotide polymorphism in the CYP2E1 gene promoter affects skatole content in backfat of boars of two commercial Duroc-sired crossbred populations.

Journal: Meat science 20121201

Title: Evaluation of various boar taint detection methods.

Journal: Animal : an international journal of animal bioscience 20121101

Title: Enantioselective cyclopropanation of indoles: construction of all-carbon quaternary stereocenters.

Journal: Organic letters 20121005

Title: Threshold detection of boar taint chemicals using parasitic wasps.

Journal: Journal of food science 20121001

Title: Directed evolution reveals requisite sequence elements in the functional expression of P450 2F1 in Escherichia coli.

Journal: Chemical research in toxicology 20120917

Title: Effect of dietary chicory on boar taint.

Journal: Meat science 20120801

Title: A human nose scoring system for boar taint and its relationship with androstenone and skatole.

Journal: Meat science 20120801

Title: Different scalding techniques do not affect boar taint.

Journal: Meat science 20120801

Title: Synthesis and cytotoxic activity of novel 3-methyl-1-[(4-substitutedpiperazin-1-yl)methyl]-1H-indole derivatives.

Journal: Arzneimittel-Forschung 20120801

Title: Genetic parameters for androstenone, skatole, indole, and human nose scores as measures of boar taint and their relationship with finishing traits.

Journal: Journal of animal science 20120701

Title: Determination of the boar taint compound skatole in meat juice by means of stable isotope dilution analysis-direct immersion-solid phase microextraction-gas chromatography/mass spectrometry.

Journal: Meat science 20120701

Title: Effect of vaccination against gonadotrophin-releasing factor on growth performance, carcass, meat and fat quality of male Duroc pigs for dry-cured ham production.

Journal: Meat science 20120601

Title: Mass spectrometry imaging of glucosinolates in Arabidopsis flowers and siliques.

Journal: Phytochemistry 20120501

Title: Synthesis of benzopyrano[4,3-b](N-arylsulfonyl)indoles and benzopyrano[3,4-b](N-arylsulfonyl)indoles via intramolecular palladium-catalyzed aryl-aryl coupling reaction.

Journal: Molecular diversity 20120501

Title: Feeding Jerusalem artichoke reduced skatole level and changed intestinal microbiota in the gut of entire male pigs.

Journal: Animal : an international journal of animal bioscience 20120501

Title: The roles of different porcine cytochrome P450 enzymes and cytochrome b5A in skatole metabolism.

Journal: Animal : an international journal of animal bioscience 20120501

Title: Respective roles of CYP2A5 and CYP2F2 in the bioactivation of 3-methylindole in mouse olfactory mucosa and lung: studies using Cyp2a5-null and Cyp2f2-null mouse models.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120401

Title: Development of the sigma-1 receptor in C-terminals of motoneurons and colocalization with the N,N'-dimethyltryptamine forming enzyme, indole-N-methyl transferase.

Journal: Neuroscience 20120329

Title: Impact of consumer's sensitivity to androstenone on acceptability of meat from entire male pigs in three European countries: France, Spain and United Kingdom.

Journal: Meat science 20120301

Title: Acceptability of entire male pork with various levels of androstenone and skatole by consumers according to their sensitivity to androstenone.

Journal: Meat science 20120201

Title: Review of analytical methods to measure boar taint compounds in porcine adipose tissue: the need for harmonised methods.

Journal: Meat science 20120101

Title: A novel, simple, and sensitive colorimetric method to determine aromatic amino acid aminotransferase activity using the Salkowski reagent.

Journal: Folia microbiologica 20120101

Title: Genome-wide association scan and phased haplotype construction for quantitative trait loci affecting boar taint in three pig breeds.

Journal: BMC genomics 20120101

Title: Molecular and cellular aspects of rhabdovirus entry.

Journal: Viruses 20120101

Title: Structure and dynamics of the G121V dihydrofolate reductase mutant: lessons from a transition-state inhibitor complex.

Journal: PloS one 20120101

Title: Investigation of the sunscreen octocrylene's interaction with amino acid analogs in the presence of UV radiation.

Journal: Photochemistry and photobiology 20120101

Title: Effects of statins on the recovery of olfactory function in a 3-methylindole-induced anosmia mouse model.

Journal: American journal of rhinology & allergy 20120101

Title: CYP2E1 and its relation with boar taint in Belgian pig breeds.

Journal: Communications in agricultural and applied biological sciences 20120101

Title: Identification of new agonists and antagonists of the insect odorant receptor co-receptor subunit.

Journal: PloS one 20120101

Title: Molecular and functional characterization of the odorant receptor2 (OR2) in the tiger mosquito Aedes albopictus.

Journal: PloS one 20120101

Title: Characterization of a novel phenol hydroxylase in indoles biotransformation from a strain Arthrobacter sp. W1 [corrected].

Journal: PloS one 20120101

Title: Effect of housing system, slaughter weight and slaughter strategy on carcass and meat quality, sex organ development and androstenone and skatole levels in Duroc finished entire male pigs.

Journal: Meat science 20111201

Title: Early immunocastration of male pigs with Improvac(®) - effect on boar taint, hormones and reproductive organs.

Journal: Vaccine 20111128

Title: Direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms.

Journal: The Journal of organic chemistry 20111104

Title: Reducing the length of time between slaughter and the secondary gonadotropin-releasing factor immunization improves growth performance and clears boar taint compounds in male finishing pigs.

Journal: Journal of animal science 20110901

Title: Development of a candidate reference method for the simultaneous quantitation of the boar taint compounds androstenone, 3α-androstenol, 3β-androstenol, skatole, and indole in pig fat by means of stable isotope dilution analysis-headspace solid-phase microextraction-gas chromatography/mass spectrometry.

Journal: Analytical chemistry 20110901

Title: Rigidized 1-aryl sulfonyl tryptamines: synthesis and pharmacological evaluation as 5-HT6 receptor ligands.

Journal: Bioorganic & medicinal chemistry letters 20110801

Title: Resynthesized lines and cultivars of Brassica napus L. provide sources of resistance to the cabbage stem weevil ( Ceutorhynchus pallidactylus (Mrsh.)).

Journal: Bulletin of entomological research 20110601

Title: Comparison of heating methods and the use of different tissues for sensory assessment of abnormal odours (boar taint) in pig meat.

Journal: Meat science 20110601

Title: Perturbations of aromatic amino acids are associated with iron cluster assembly in ribonucleotide reductase.

Journal: Journal of the American Chemical Society 20110511

Title: Effects of dietary components including garlic on concentrations of skatole and indole in subcutaneous fat of female pigs.

Journal: Meat science 20110501

Title: Prevalence and relationships of sensory taint, 5α-androstenone and skatole in fat and lean tissue from the loin (Longissimus dorsi) of barrows, gilts, sows, and boars from selected abattoirs in the United States.

Journal: Meat science 20110501

Title: The reaction of azoles with 17-chloro-16-formylandrosta-5,16-dien-3β-yl-acetate: synthesis and structural elucidation of novel 16-azolylmethylene-17-oxoandrostanes.

Journal: Steroids 20110501

Title: Quantification of binding affinities of essential sugars with a tryptophan analogue and the ubiquitous role of C-H···π interactions.

Journal: Physical chemistry chemical physics : PCCP 20110414

Title: Influence of soiling on boar taint in boars.

Journal: Meat science 20110301

Title: The volatile profile of longissimus dorsi muscle of heifers fed pasture, pasture silage or cereal concentrate: implication for dietary discrimination.

Journal: Meat science 20110301

Title: Radical-mediated enzymatic carbon chain fragmentation-recombination.

Journal: Nature chemical biology 20110301

Title: Revealing genetic relationships between compounds affecting boar taint and reproduction in pigs.

Journal: Journal of animal science 20110301

Title: Lung adenocarcinoma originates from retrovirus infection of proliferating type 2 pneumocytes during pulmonary post-natal development or tissue repair.

Journal: PLoS pathogens 20110301

Title: Novel escape mutants suggest an extensive TRIM5α binding site spanning the entire outer surface of the murine leukemia virus capsid protein.

Journal: PLoS pathogens 20110301

Title: In vitro cytochrome P450 2E1 and 2A activities in the presence of testicular steroids.

Journal: Reproduction in domestic animals = Zuchthygiene 20110201

Title: Navigating the human metabolome for biomarker identification and design of pharmaceutical molecules.

Journal: Journal of biomedicine & biotechnology 20110101

Title: Tryptophan orientations in membrane-bound gramicidin and melittin-a comparative linear dichroism study on transmembrane and surface-bound peptides.

Journal: Biochimica et biophysica acta 20110101

Title: The distal end of porcine chromosome 6p is involved in the regulation of skatole levels in boars.

Journal: BMC genetics 20110101

Title: Boar taint detection using parasitoid biosensors.

Journal: Journal of food science 20110101

Title: Four small puzzles that Rosetta doesn't solve.

Journal: PloS one 20110101

Title: Large scale genome-wide association and LDLA mapping study identifies QTLs for boar taint and related sex steroids.

Journal: BMC genomics 20110101

Title: Structural Chemistry of Human SET Domain Protein Methyltransferases.

Journal: Current chemical genomics 20110101

Title: Morphological and geochemical evidence of eumelanin preservation in the feathers of the Early Cretaceous bird, Gansus yumenensis.

Journal: PloS one 20110101

Title: Identification of odorous compounds in reclaimed water using FPA combined with sensory GC-MS.

Journal: Journal of environmental sciences (China) 20110101

Title: Insights into auxin signaling in plant-pathogen interactions.

Journal: Frontiers in plant science 20110101

Title: Relationship between olfactory function and olfactory neuronal population in C57BL6 mice injected intraperitoneally with 3-methylindole.

Journal: Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery 20101201

Title: Potent mutagenicity of 3-methylindole requires pulmonary cytochrome P450-mediated bioactivation: a comparison to the prototype cigarette smoke mutagens B(a)P and NNK.

Journal: Chemical research in toxicology 20101115

Title: Ab initio calculation of resonance Raman cross sections based on excited state geometry optimization.

Journal: The journal of physical chemistry. A 20101104

Title: Expression of transient receptor potential channel vanilloid (TRPV) 1–4, melastin (TRPM) 5 and 8, and ankyrin (TRPA1) in the normal and methimazole-treated mouse olfactory epithelium.

Journal: Acta oto-laryngologica 20101101

Title: Norwegian consumers' acceptability of boar tainted meat with different levels of androstenone or skatole as related to their androstenone sensitivity.

Journal: Meat science 20101101

Title: Protein flexibility and conformational entropy in ligand design targeting the carbohydrate recognition domain of galectin-3.

Journal: Journal of the American Chemical Society 20101020

Title: Spectroscopic properties of the receptors based on 2- and 3-linked tri(indolyl)methanes for anion binding.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20101015

Title: Analysis of measured and calculated Raman spectra of indole, 3-methylindole, and tryptophan on the basis of observed and predicted isotope shifts.

Journal: The journal of physical chemistry. A 20101014

Title: Differences in testosterone, androstenone, and skatole levels in plasma and fat between pubertal purebred Duroc and Landrace boars in response to human chorionic gonadotrophin stimulation.

Journal: Theriogenology 20101001

Title: The effects of method of castration, rearing condition and diet on sensory quality of pork assessed by a trained panel.

Journal: Meat science 20101001

Title: The seed composition of Arabidopsis mutants for the group 3 sulfate transporters indicates a role in sulfate translocation within developing seeds.

Journal: Plant physiology 20101001

Title: Odorant receptor from the southern house mosquito narrowly tuned to the oviposition attractant skatole.

Journal: Journal of chemical ecology 20100801

Title: Enantioselective oxidative cross-coupling reaction of 3-indolylmethyl C-H bonds with 1,3-dicarbonyls using a chiral Lewis acid-bonded nucleophile to control stereochemistry.

Journal: Angewandte Chemie (International ed. in English) 20100726

Title: Blue shifted hydrogen bond in 3-methylindole.CHX(3) complexes (X = Cl, F).

Journal: Physical chemistry chemical physics : PCCP 20100707

Title: Bovine atypical interstitial pneumonia.

Journal: The Veterinary clinics of North America. Food animal practice 20100701

Title: Removing the mustard oil bomb from seeds: transgenic ablation of myrosin cells in oilseed rape (Brassica napus) produces MINELESS seeds.

Journal: Journal of experimental botany 20100601

Title: QM/MM methods: looking inside heme proteins biochemistry.

Journal: Biophysical chemistry 20100601

Title: Characterization of porcine pregnane X receptor, farnesoid X receptor and their splice variants.

Journal: Experimental biology and medicine (Maywood, N.J.) 20100601

Title: Transplantation of neural stem cells in anosmic mice.

Journal: Clinical and experimental otorhinolaryngology 20100601

Title: Formation of covalently bound protein adducts from the cytotoxicant naphthalene in nasal epithelium: species comparisons.

Journal: Environmental health perspectives 20100501

Title: Culex mosquitoes (Diptera: Culicidae) egg laying in traps loaded with Bacillus thuringiensis variety israelensis and baited with skatole.

Journal: Journal of medical entomology 20100501

Title: Variable glucosinolate profiles of Cardamine pratensis (Brassicaceae) with equal chromosome numbers.

Journal: Journal of agricultural and food chemistry 20100428

Title: Examination of testicular gene expression patterns in Yorkshire pigs with high and low levels of boar taint.

Journal: Animal biotechnology 20100401

Title: 3-Methylindole metabolites induce lung CYP1A1 and CYP2F1 enzymes by AhR and non-AhR mechanisms, respectively.

Journal: Chemical research in toxicology 20100315

Title: Knockdown of a mosquito odorant-binding protein involved in the sensitive detection of oviposition attractants.

Journal: Journal of chemical ecology 20100301

Title: A novel approach to 3-methylindoles by a Heck/cyclization/isomerization process.

Journal: Organic letters 20100219

Title: Formation, isomerization, and dissociation of alpha-carbon-centered and pi-centered glycylglycyltryptophan radical cations.

Journal: The journal of physical chemistry. B 20100218

Title: Dihalide and pseudohalide radical anions as oxidizing agents in nonaqueous solvents.

Journal: The journal of physical chemistry. A 20100121

Title: Reorientations of aromatic amino acids and their side chain models: anisotropy measurements and molecular dynamics simulations.

Journal: The journal of physical chemistry. A 20100114

Title: Molecular dynamics simulations reveal that AEDANS is an inert fluorescent probe for the study of membrane proteins.

Journal: European biophysics journal : EBJ 20100101

Title: Atypical interstitial pneumonia in grazing adult red deer (Cervus elaphus).

Journal: Journal of comparative pathology 20100101

Title: The Anopheles gambiae odorant binding protein 1 (AgamOBP1) mediates indole recognition in the antennae of female mosquitoes.

Journal: PloS one 20100101

Title: Effects of statins on regeneration of olfactory epithelium.

Journal: American journal of rhinology & allergy 20100101

Title: An odorant receptor from the southern house mosquito Culex pipiens quinquefasciatus sensitive to oviposition attractants.

Journal: PloS one 20100101

Title: Olfactory dysfunction in Parkinson's disease: Benefits of quantitative odorant examination.

Journal: International journal of general medicine 20100101

Title: Antennal expression pattern of two olfactory receptors and an odorant binding protein implicated in host odor detection by the malaria vector Anopheles gambiae.

Journal: International journal of biological sciences 20100101

Title: Whole genome co-expression analysis of soybean cytochrome P450 genes identifies nodulation-specific P450 monooxygenases.

Journal: BMC plant biology 20100101

Title: Metal oxide sensors for electronic noses and their application to food analysis.

Journal: Sensors (Basel, Switzerland) 20100101

Title: Sulfur, not too far behind O, N, and C: SH...pi hydrogen bond.

Journal: The journal of physical chemistry. A 20091119

Title: Nature of the N-H...S hydrogen bond.

Journal: The journal of physical chemistry. A 20091119

Title: 3-Methylindole is mutagenic and a possible pulmonary carcinogen.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20091101

Title: Synthesis and structure-activity relationships of pyrazolodiazepine derivatives as human P2X7 receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20091101

Title: Optimal experimental design for parameter estimation of a cell signaling model.

Journal: PLoS computational biology 20091101

Title: {2-[Bis(3-methyl-1H-indol-2-yl)meth-yl]phenolato-κO}dimeth-yl(tetra-hydro-furan-κO)aluminium(III).

Journal: Acta crystallographica. Section E, Structure reports online 20091101

Title: Nosiheptide biosynthesis featuring a unique indole side ring formation on the characteristic thiopeptide framework.

Journal: ACS chemical biology 20091016

Title: The pneumotoxin 3-methylindole is a substrate and a mechanism-based inactivator of CYP2A13, a human cytochrome P450 enzyme preferentially expressed in the respiratory tract.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091001

Title: Volatile components from selected Tahitian liverworts.

Journal: Natural product communications 20091001

Title: Effect of a gonadotropin-releasing factor vaccine on follicle-stimulating hormone and luteinizing hormone concentrations and on the development of testicles and the expression of boar taint in male pigs.

Journal: Theriogenology 20090915

Title: Characterization and quantification of odor-active compounds in unsaturated fatty acid/conjugated linoleic acid (UFA/CLA)-enriched butter and in conventional butter during storage and induced oxidation.

Journal: Journal of agricultural and food chemistry 20090826

Title: Plant antimicrobial agents and their effects on plant and human pathogens.

Journal: International journal of molecular sciences 20090801

Title: Effect of nitroethane and nitroethanol on the production of indole and 3-methylindole (skatole) from bacteria in swine feces by gas chromatography.

Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20090801

Title: Electronic structure of aromatic amino acids studied by soft x-ray spectroscopy.

Journal: The Journal of chemical physics 20090721

Title: Excited-state geometry method for calculation of the absolute resonance Raman cross sections of the aromatic amino acids.

Journal: The journal of physical chemistry. A 20090507

Title: Mechanism of the very efficient quenching of tryptophan fluorescence in human gamma D- and gamma S-crystallins: the gamma-crystallin fold may have evolved to protect tryptophan residues from ultraviolet photodamage.

Journal: Biochemistry 20090505

Title: Development of a defined medium for Clostridium scatologenes ATCC 25775.

Journal: Letters in applied microbiology 20090401

Title: Evaluation of indole-based probes for high-throughput screening of drug binding to human serum albumin: Analysis by high-performance affinity chromatography.

Journal: Journal of separation science 20090401

Title: Solvent effects on the fluorescence quenching of tryptophan by amides via electron transfer. Experimental and computational studies.

Journal: The journal of physical chemistry. B 20090305

Title: The gene controlling the indole glucosinolate modifier1 quantitative trait locus alters indole glucosinolate structures and aphid resistance in Arabidopsis.

Journal: The Plant cell 20090301

Title: Detection of odorous compounds in breath.

Journal: Journal of dental research 20090301

Title: 3-Methylindole production is regulated in Clostridium scatologenes ATCC 25775.

Journal: Letters in applied microbiology 20090101

Title: Fe(III) stimulates 3-methylindole and 4-methylphenol production in swine lagoon enrichments and Clostridium scatologenes ATCC 25775.

Journal: Letters in applied microbiology 20090101

Title: Latherin: a surfactant protein of horse sweat and saliva.

Journal: PloS one 20090101

Title: Association between SNPs within candidate genes and compounds related to boar taint and reproduction.

Journal: BMC genetics 20090101

Title: A comparative genomics approach to understanding the biosynthesis of the sunscreen scytonemin in cyanobacteria.

Journal: BMC genomics 20090101

Title: Porcine CYP2A19, CYP2E1 and CYP1A2 forms are responsible for skatole biotransformation in the reconstituted system.

Journal: Neuro endocrinology letters 20090101

Title: Design, structure-activity relationships, X-ray crystal structure, and energetic contributions of a critical P1 pharmacophore: 3-chloroindole-7-yl-based factor Xa inhibitors.

Journal: Journal of medicinal chemistry 20081211

Title: The chromatin remodeler SPLAYED regulates specific stress signaling pathways.

Journal: PLoS pathogens 20081201

Title: Carbohydrate-protein recognition probed by density functional theory and ab initio calculations including dispersive interactions.

Journal: Physical chemistry chemical physics : PCCP 20081121

Title: Mechanism of the efficient tryptophan fluorescence quenching in human gammaD-crystallin studied by time-resolved fluorescence.

Journal: Biochemistry 20081007

Title: Long-term effect of vaccination against gonadotropin-releasing hormone, using Improvac, on hormonal profile and behaviour of male pigs.

Journal: Animal reproduction science 20081001

Title: Single mutations change CYP2F3 from a dehydrogenase of 3-methylindole to an oxygenase.

Journal: Biochemistry 20080916

Title: Effect of a gonadotropin-releasing hormone vaccine (Improvac) on steroid hormones, boar taint compounds and performance in entire male pigs.

Journal: Reproduction in domestic animals = Zuchthygiene 20080601

Title: L-tryptophan radical cation electron spin resonance studies: connecting solution-derived hyperfine coupling constants with protein spectral interpretations.

Journal: Journal of the American Chemical Society 20080521

Title: Field sampling method for quantifying odorants in humid environments.

Journal: Environmental science & technology 20080515

Title: Testicular germ cell development in relation to 5alpha-androstenone levels in pubertal entire male pigs.

Journal: Theriogenology 20080501

Title: Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds.

Journal: Molecular diversity 20080501

Title: Semiochemicals of the Scarabaeinae VIII. Identification of active constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper bonellii, using gas chromatography with flame ionization and electroantennographic detection in parallel.

Journal: Journal of chromatography. A 20080404

Title: Dual negative precursor ion scan approach for rapid detection of glutathione conjugates using liquid chromatography/tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20080401

Title: Effects of hCG stimulation on hepatic activities of cytochromes P4502E1 and P4502A in pubertal male pigs.

Journal: Reproduction in domestic animals = Zuchthygiene 20080401

Title: Volatile components of Discaria americana Gillies & Hook (Rhamnaceae).

Journal: Natural product research 20080215

Title: ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis.

Journal: Phytochemistry 20080201

Title: Metabolic activation of a novel 3-substituted indole-containing TNF-alpha inhibitor: dehydrogenation and inactivation of CYP3A4.

Journal: Chemical research in toxicology 20080201

Title: The effect of a c.-8G>T polymorphism on the expression of cytochrome b5A and boar taint in pigs.

Journal: Animal genetics 20080201

Title: Performance of generalist and specialist herbivores and their endoparasitoids differs on cultivated and wild Brassica populations.

Journal: Journal of chemical ecology 20080201

Title: Regulation of CYP2A6 protein expression by skatole, indole, and testicular steroids in primary cultured pig hepatocytes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080101

Title: Mechanism-based inactivation of lung-selective cytochrome P450 CYP2F enzymes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080101

Title: Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: a review.

Journal: Genetics, selection, evolution : GSE 20080101

Title: Equilibrium sampling used to monitor malodors in a Swine waste lagoon.

Journal: Journal of environmental quality 20080101

Title: Biotransformation of indole derivatives by mycelial cultures.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101

Title: Effect of ginkgo biloba and dexamethasone in the treatment of 3-methylindole-induced anosmia mouse model.

Journal: American journal of rhinology 20080101

Title: Gene expression profiles in liver of pigs with extreme high and low levels of androstenone.

Journal: BMC veterinary research 20080101

Title: Reverse and conventional chemical ecology approaches for the development of oviposition attractants for Culex mosquitoes.

Journal: PloS one 20080101

Title: Development and validation of a method for simultaneous analysis of the boar taint compounds indole, skatole and androstenone in pig fat using liquid chromatography-multiple mass spectrometry.

Journal: Journal of chromatography. A 20071207

Title: Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.

Journal: Journal of medicinal chemistry 20071115

Title: Sensory-directed identification of creaminess-enhancing volatiles and semivolatiles in full-fat cream.

Journal: Journal of agricultural and food chemistry 20071114

Title: Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering.

Journal: Analytical chemistry 20071101

Title: Dehydrogenation of indoline by cytochrome P450 enzymes: a novel 'aromatase' process.

Journal: The Journal of pharmacology and experimental therapeutics 20070801

Title: Effects of dietary crude protein level on odour from pig manure.

Journal: Animal : an international journal of animal bioscience 20070601

Title: Development of indolequinone mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1): NQO1 inhibition and growth inhibitory activity in human pancreatic MIA PaCa-2 cancer cells.

Journal: Biochemistry 20070522

Title: Characterization of skatole-producing microbial populations in enriched swine lagoon slurry.

Journal: FEMS microbiology ecology 20070501

Title: [Identification of volatile organic compounds in the manures of cow, hog and chicken by solid phase microextraction coupled with gas chromatography/mass spectrometry].

Journal: Se pu = Chinese journal of chromatography 20070501

Title: Actions between neonicotinoids and key residues of insect nAChR based on an ab initio quantum chemistry study: hydrogen bonding and cooperative pi-pi interaction.

Journal: Bioorganic & medicinal chemistry 20070401

Title: Olfactory performance of rats after selective deafferentation of the olfactory bulb by 3-methyl indole.

Journal: Chemical senses 20070201

Title: Metabolism and bioactivation of 3-methylindole by human liver microsomes.

Journal: Chemical research in toxicology 20070101

Title: [Exploratory activity of mice of different genetic strains after olfaction disruption by 3-methylindole (skatole)].

Journal: Izvestiia Akademii nauk. Seriia biologicheskaia 20070101

Title: Calculation of the free energy and cooperativity of protein folding.

Journal: PloS one 20070101

Title: Exploratory behavior and anxiety level of white outbred rats after blocking olfaction with N-trimethylindole (skatole).

Journal: Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections 20070101

Title: The role of hydrophobic interactions in positioning of peripheral proteins in membranes.

Journal: BMC structural biology 20070101

Title: Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.

Journal: BMC genomics 20070101

Title: Orientation and exploratory behavior and anxiety of CBA mice with anosmia induced by N-trimethylindole (skatole).

Journal: Bulletin of experimental biology and medicine 20070101

Title: Assessment of SULT1A1, CYP2A6 and CYP2C18 as candidate genes for elevated backfat skatole levels in commercial and experimental pig populations.

Journal: Animal genetics 20061001

Title: Characterization of livestock odors using steel plates, solid-phase microextraction, and multidimensional gas chromatography-mass spectrometry-olfactometry.

Journal: Journal of the Air & Waste Management Association (1995) 20061001

Title: Structure and reactivity of Trypanosoma brucei pteridine reductase: inhibition by the archetypal antifolate methotrexate.

Journal: Molecular microbiology 20060901

Title: Flavor improvement in pork from barrows and gilts via inhibition of intestinal skatole formation with resistant potato starch.

Journal: Journal of agricultural and food chemistry 20060809

Title: Role of the intermolecular vibrations in the hydrogen transfer rate: the 3-methylindole-NH3 complex.

Journal: The journal of physical chemistry. A 20060803

Title: Characterizing developmental changes in plasma and tissue skatole concentrations in the prepubescent intact male pig.

Journal: Journal of animal science 20060701

Title: Effect of dietary melengestrol acetate on the incidence of acute interstitial pneumonia in feedlot heifers.

Journal: Canadian journal of veterinary research = Revue canadienne de recherche veterinaire 20060701

Title: Enzymatic properties of human CYP2W1 expressed in Escherichia coli.

Journal: Biochemical and biophysical research communications 20060623

Title: Fragmentation of peptides with N-terminal dimethylation and imine/methylol adduction at the tryptophan side-chain.

Journal: Journal of the American Society for Mass Spectrometry 20060601

Title: Production of indolic compounds by rumen bacteria isolated from grazing ruminants.

Journal: Journal of applied microbiology 20060601

Title: Functional polymorphism in porcine CYP2E1 gene: Its association with skatole levels.

Journal: The Journal of steroid biochemistry and molecular biology 20060601

Title: The role of CYP2A and CYP2E1 in the metabolism of 3-methylindole in primary cultured porcine hepatocytes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Insulin-like growth factor binding protein-2: contributions of the C-terminal domain to insulin-like growth factor-1 binding.

Journal: Molecular pharmacology 20060301

Title: Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.

Journal: Chemical research in toxicology 20060301

Title: Photoreaction between benzoylthiophenes and N-BOC-tryptophan methyl ester.

Journal: Photochemistry and photobiology 20060101

Title: CYP4B1: an enigmatic P450 at the interface between xenobiotic and endobiotic metabolism.

Journal: Drug metabolism reviews 20060101

Title: Bias of Tedlar bags in the measurement of agricultural odorants.

Journal: Journal of environmental quality 20060101

Title: Importance of tensor asymmetry for the analysis of 2H NMR spectra from deuterated aromatic rings.

Journal: Journal of the American Chemical Society 20051214

Title: Boar taint is related to endocrine and anatomical changes at puberty but not to aggressive behaviour in entire male pigs.

Journal: Reproduction in domestic animals = Zuchthygiene 20051201

Title: Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20051101

Title: Cloning and mapping of the porcine cytochrome-p450 2E1 gene and its association with skatole levels in the domestic pig.

Journal: Animal genetics 20051001

Title: Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme.

Journal: Chemical research in toxicology 20050901

Title: Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.

Journal: Journal of agricultural and food chemistry 20050727

Title: Role of the fermentation process in off-odorant formation in white pepper: on-site trial in Thailand.

Journal: Journal of agricultural and food chemistry 20050727

Title: Insights into the role of the aromatic residue in galactose-binding sites: MP2/6-311G++** study on galactose- and glucose-aromatic residue analogue complexes.

Journal: Biochemistry 20050614

Title: Dose-dependent effects of resistant potato starch in the diet on intestinal skatole formation and adipose tissue accumulation in the pig.

Journal: Journal of veterinary medicine. A, Physiology, pathology, clinical medicine 20050601

Title: Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.

Journal: Bioorganic & medicinal chemistry 20050516

Title: Examining the risks and benefits of replacing traditional dose-response with hormesis.

Journal: Human & experimental toxicology 20050501

Title: Free oestrone in adipose tissue and its relation to androstenone and skatole in entire male pigs.

Journal: Reproduction in domestic animals = Zuchthygiene 20050401

Title: Effects of resistant potato starch on odor emission from feces in Swine production units.

Journal: Journal of agricultural and food chemistry 20050223

Title: Bayesian analysis of quantitative trait loci for boar taint in a Landrace outbred population.

Journal: Journal of animal science 20050201

Title: Detection of quantitative trait loci for androstenone, skatole and boar taint in a cross between Large White and Meishan pigs.

Journal: Animal genetics 20050201

Title: Use of ultrasonic vocalizations to assess olfactory detection in mouse pups treated with 3-methylindole.

Journal: Behavioural processes 20050131

Title: Chemical changes induced by methyl jasmonate in oilseed rape grown in the laboratory and in the field.

Journal: Journal of agricultural and food chemistry 20041215

Title: Structure and function of the C-terminal domain of the polymerase cofactor of rabies virus.

Journal: Journal of molecular biology 20041029

Title: Stark absorption spectroscopy of indole and 3-methylindole.

Journal: The Journal of chemical physics 20040908

Title: Semiochemistry of the goldeneyed lacewing Chrysopa oculata: attraction of males to a male-produced pheromone.

Journal: Journal of chemical ecology 20040901

Title: Selective tryptophan modification with rhodium carbenoids in aqueous solution.

Journal: Journal of the American Chemical Society 20040825

Title: Molecular cloning, expression and functional characterization of the cytochrome P450 2A6 gene in pig liver.

Journal: Animal genetics 20040801

Title: Age-related variation of plasma concentrations of skatole, androstenone, testosterone, oestradiol-17 beta, oestrone sulphate, dehydroepiandrosterone sulphate, triiodothyronine and IGF-1 in six entire male pigs.

Journal: Reproduction in domestic animals = Zuchthygiene 20040601

Title: Excretion of major odor-causing and acidifying compounds in response to dietary supplementation of chicory inulin in growing pigs.

Journal: Journal of animal science 20040601

Title: Use of a chemical trigger for electron transfer to characterize a precursor to cluster X in assembly of the iron-radical cofactor of Escherichia coli ribonucleotide reductase.

Journal: Biochemistry 20040525

Title: Laboratory and field responses of the mosquito, Culex quinquefasciatus, to plant-derived Culex spp. oviposition pheromone and the oviposition cue skatole.

Journal: Journal of chemical ecology 20040501

Title: A direct access to 3-(2-Oxoalkyl)indoles via aluminum chloride induced C-C bond formation.

Journal: The Journal of organic chemistry 20040416

Title: Structural and catalytic diversity in the two family 11 aldo-keto reductases.

Journal: Journal of molecular biology 20040326

Title: Mass analyzed threshold ionization spectroscopy of 5-methylindole and 3-methylindole cations and the methyl substitution effect.

Journal: The Journal of chemical physics 20040315

Title: Molecular cloning and functional analysis of porcine SULT1A1 gene and its variant: a single mutation SULT1A1 causes a significant decrease in sulfation activity.

Journal: Mammalian genome : official journal of the International Mammalian Genome Society 20040301

Title: Photoaffinity labeling identifies the substrate-binding site of mammalian squalene epoxidase.

Journal: Biochemical and biophysical research communications 20040227

Title: Fat volatiles tracers of grass feeding in sheep.

Journal: Meat science 20040201

Title: Environmental swap energy and role of configurational entropy in transfer of small molecules from water into alkanes.

Journal: The Journal of chemical physics 20040115

Title: Study on the organoleptic intensity scale for measuring oral malodor.

Journal: Journal of dental research 20040101

Title: (Z)-2-(1H-Indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one.

Journal: Acta crystallographica. Section C, Crystal structure communications 20040101

Title: Evoked response to olfactory stimulations in anosmic patients.

Journal: The international tinnitus journal 20040101

Title: Use of a novel group of oral malodor measurements to evaluate an anti-oral malodor mouthrinse (TriOralTM) in humans.

Journal: The Journal of clinical dentistry 20040101

Title: Steady-state and time-resolved studies on the formation of skatolyl radicals photosensitized by 2-benzoylthiophene.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20031101

Title: Field and laboratory evaluations of potential oviposition attractants for Aedes albopictus (Diptera: Culicidae).

Journal: Journal of the American Mosquito Control Association 20030901

Title: Rapid formation of non-native contacts during the folding of HPr revealed by real-time photo-CIDNP NMR and stopped-flow fluorescence experiments.

Journal: Journal of molecular biology 20030704

Title: 3-methylindole induces transient olfactory mucosal injury in ponies.

Journal: Veterinary pathology 20030701

Title: Characterization of pulmonary CYP4B2, specific catalyst of methyl oxidation of 3-methylindole.

Journal: Molecular pharmacology 20030501

Title: Phase II in vitro metabolism of 3-methylindole metabolites in porcine liver.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20030501

Title: Time profile of putrescine, cadaverine, indole and skatole in human saliva.

Journal: Archives of oral biology 20030401

Title: Identification of oxidation products and free radicals of tryptophan by mass spectrometry.

Journal: Journal of the American Society for Mass Spectrometry 20030401

Title: Psychophysical evaluation of responses to pleasant and mal-odour stimulation in human subjects; adaptation, dose response and gender differences.

Journal: International journal of psychophysiology : official journal of the International Organization of Psychophysiology 20030401

Title: Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations.

Journal: Organic & biomolecular chemistry 20030207

Title: 3-methylindole-induced toxicity to human bronchial epithelial cell lines.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20030201

Title: Cholecystectomy and the risk for developing colorectal cancer and distal colorectal adenomas.

Journal: British journal of cancer 20030113

Title: Solution structure of a circular-permuted variant of the potent HIV-inactivating protein cyanovirin-N: structural basis for protein stability and oligosaccharide interaction.

Journal: Journal of molecular biology 20030103

Title: Hydantoin-substituted 4,6-dichloroindole-2-carboxylic acids as ligands with high affinity for the glycine binding site of the NMDA receptor.

Journal: Journal of medicinal chemistry 20030102

Title: Fluorescence determination of tryptophan side-chain accessibility and dynamics in triple-helical collagen-like peptides.

Journal: Biophysical journal 20030101

Title: Ultrastructural changes and olfactory deficits during 3-methylindole-induced olfactory mucosal necrosis and repair in mice.

Journal: Ultrastructural pathology 20030101

Title: Lasting chemiluminescence of 3-indoleglyoxylyl chloride and its enhancement.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030101

Title: Effects of butyrate on apoptosis in the pig colon and its consequences for skatole formation and tissue accumulation.

Journal: Journal of animal science 20030101

Title: Effects of feeding aspirin and supplemental vitamin E on plasma concentrations of 3-methylindole, 3-methyleneindolenine-adduct concentrations in blood and pulmonary tissues, lung lesions, and growth performance in feedlot cattle.

Journal: American journal of veterinary research 20021201

Title: Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.

Journal: Journal of the American Chemical Society 20020925

Title: Odor discrimination and odor quality perception in rats with disruption of connections between the olfactory epithelium and olfactory bulbs.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020515

Title: Modifying rates of reductive elimination of leaving groups from indolequinone prodrugs: a key factor in controlling hypoxia-selective drug release.

Journal: Biochemical pharmacology 20020501

Title: Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes.

Journal: Chemico-biological interactions 20020420

Title: Time-dependent changes in plasma concentrations of 3-methylindole and blood concentrations of 3-methyleneindolenine-adduct in feedlot cattle.

Journal: American journal of veterinary research 20020401

Title: Effects of fructooligosaccharide on conversion of L-tryptophan to skatole and indole by mixed populations of pig fecal bacteria.

Journal: The Journal of general and applied microbiology 20020401

Title: Semiochemicals of the Scarabaeinae: VI. Identification of EAD-active constituents of abdominal secretion of male dung beetle, Kheper nigroaeneus.

Journal: Journal of chemical ecology 20020301

Title: Volatile flavor components of stored nonfat dry milk.

Journal: Journal of agricultural and food chemistry 20020116

Title: Olfactory cues for oviposition behavior in Toxorhynchites moctezuma and Toxorhynchites amboinensis (Diptera: Culicidae).

Journal: Journal of medical entomology 20020101

Title: Indole-3-acetic acids and horseradish peroxidase: a new prodrug/enzyme combination for targeted cancer therapy.

Journal: Current pharmaceutical design 20020101

Title: Chemiluminescence associated with amino acid oxidation mediated by hypochlorous acid.

Journal: Luminescence : the journal of biological and chemical luminescence 20020101

Title: Relationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganisms.

Journal: Marine pollution bulletin 20020101

Title: Molecular modelling of the mouse cytochrome P450 CYP2F2 based on the CYP102 crystal structure template and selective CYP2F2 substrate interactions.

Journal: Drug metabolism and drug interactions 20020101

Title: Detection of DNA adducts using a quantitative long PCR technique and the fluorogenic 5' nuclease assay (TaqMan).

Journal: Mutation research 20011212

Title: Association of 3-methyleneindolenine, a toxic metabolite of 3-methylindole, with acute interstitial pneumonia in feedlot cattle.

Journal: American journal of veterinary research 20011001

Title: Vaccination of boars with a GnRH vaccine (Improvac) eliminates boar taint and increases growth performance.

Journal: Journal of animal science 20011001

Title: Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2.

Journal: Journal of medicinal chemistry 20010927

Title: Identification of mucosal injury in the murine nasal airways by magnetic resonance imaging: site-specific lesions induced by 3-methylindole.

Journal: Toxicology and applied pharmacology 20010815

Title: Detection and characterization of DNA adducts of 3-methylindole.

Journal: Chemical research in toxicology 20010801

Title: Selective dehydrogenation/oxygenation of 3-methylindole by cytochrome p450 enzymes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20010701

Title: Olfactory marker protein immunohistochemistry and the anterograde transport of horseradish peroxidase as indices of damage to the olfactory epithelium.

Journal: Chemical senses 20010701

Title: Olfactory memory in the mosquito Culex quinquefasciatus.

Journal: Medical and veterinary entomology 20010601

Title: Odorants as cell-type specific activators of a heat shock response in the rat olfactory mucosa.

Journal: The Journal of comparative neurology 20010416

Title: Exciplex-type behavior and partition of 3-substituted indole derivatives in reverse micelles made with benzylhexadecyldimethylammonium chloride, water and benzene.

Journal: Photochemistry and photobiology 20010201

Title: Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists.

Journal: Drug design and discovery 20010101

Title: [Aerobic methylobacteria are capable of synthesizing auxins].

Journal: Mikrobiologiia 20010101

Title: Bioactivation of toxicants by cytochrome p450-mediated dehydrogenation mechanisms.

Journal: Advances in experimental medicine and biology 20010101

Title: Metabolism of 3-methylindole by porcine liver microsomes: responsible cytochrome P450 enzymes.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20000601

Title: Attractants for synanthropic flies. Identification of attractants and coattractants for Hippelates eye gnats (Diptera: Chloropidae).

Journal: Journal of agricultural and food chemistry 19760101

Title: Kurata K, et al. Skatole regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38. Biochem Biophys Res Commun. 2019 Mar 19;510(4):649-655.

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Tags:83-34-1 Molecular Formula|83-34-1 MDL|83-34-1 SMILES|83-34-1 3-Methylindole |Heterocyclic_Building_Blocks |Organic_Building_Blocks