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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 |
| Melting Point: | 56.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 263.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 0.007000 mmHg @ 25.00 °C. (est) |
| Flash Point: | > 230.00 °F. TCC ( > 110.00 °C. )
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| logP (o/w): | 0.230 |
| Soluble in: |
| | water, 8.246e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
intraperitoneal-chicken LD50 210 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
oral-chicken LD50 590 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
intraperitoneal-mouse LD50 165 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
oral-mouse LD50 370 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
intraperitoneal-rabbit LDLo 120 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
oral-rat LD50 751 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: TREMOR
GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 89, Pg. 175, 1987.
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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 4-methyl imidazole usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for 4-methyl imidazole 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:
| 1H- | imidazole, 4-methyl- | | | imidazole, 4-methyl-
| | 1H- | imidazole, 5-methyl- | | 4- | methyl-1H-imidazole | | 5- | methyl-1H-imidazole | | 4- | methylimidazole | | 4(or 5)- | methylimidazole |
Articles:
| PubMed:Second generation silver(I)-mediated imidazole base pairs. |
| PubMed:Separation and determination of 4-methylimidazole, 2-methylimidazole and 5-hydroxymethylfurfural in beverages by amino trap column coupled with pulsed amperometric detection. |
| PubMed:Short communication: Amino trap column improving the separation of methylimidazoles, 5-hydroxymethyl-2-furaldehyde, and sugars in Maillard reaction. |
| PubMed:Structural insight into activity enhancement and inhibition of H64A carbonic anhydrase II by imidazoles. |
| PubMed:Determination of caramel colorants' by-products in liquid foods by ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). |
| PubMed:Combined EXAFS and DFT structure calculations provide structural insights into the 1:1 multi-histidine complexes of Cu(II) , Cu(I) , and Zn(II) with the tandem octarepeats of the mammalian prion protein. |
| PubMed:Observation of the slow, Debye-like relaxation in hydrogen-bonded liquids by dynamic light scattering. |
| PubMed:Determination of 4-Methylimidazole and 2-Acetyl-4()- tetrahydroxybutylimidazole in Caramel Color and Processed Foods by LC-MS/MS. |
| PubMed:SAR genotoxicity and tumorigenicity predictions for 2-MI and 4-MI using multiple SAR software. |
| PubMed:Photoinduced electron transfer from PbS quantum dots to cobalt(III) Schiff base complexes: light activation of a protein inhibitor. |
| PubMed:Comparison and evaluation of five types of imidazole-modified silica adsorbents for the removal of 2,4-dinitrophenol from water samples with the methyl group at different positions of imidazolium ring. |
| PubMed:Formation of 4(5)-methylimidazole and its precursors, α-dicarbonyl compounds, in Maillard model systems. |
| PubMed:Direct analysis of 4-methylimidazole in foods using paper spray mass spectrometry. |
| PubMed:Synthesis, crystal structure, spectroscopic, fluorescent, thermal properties and EPR spectra of doped Cu2+ ions in [Cd(sac)2(H2O)2(meim)2] single crystal. |
| PubMed:Evaluating consistency in the interpretation of NTP rodent cancer bioassays: an examination of mouse lung tumor effects in the 4-MEI study. |
| PubMed:The structure of azines derived from C-formyl-1H-imidazoles in solution and in the solid state: tautomerism, configurational and conformational studies. |
| PubMed:Determination of 2-methylimidazole and 4-methylimidazole in caramel colors by capillary electrophoresis. |
| PubMed:Carcinogenic 4(5)-methylimidazole found in beverages, sauces, and caramel colors: chemical properties, analysis, and biological activities. |
| PubMed:Axial ligand exchange of N-heterocyclic cobalt(III) Schiff base complexes: molecular structure and NMR solution dynamics. |
| PubMed:Formation of carcinogenic 4(5)-methylimidazole in caramel model systems: a role of sulphite. |
| PubMed:Determination of 2-methylimidazole, 4-methylimidazole and 2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole in caramel colours and cola using LC/MS/MS. |
| PubMed:Switching orientation of two axial imidazole ligands between parallel and perpendicular in low-spin Fe(III) and Fe(II) nonplanar porphyrinates. |
| PubMed:Carcinogenicity and regulation of caramel colorings. |
| PubMed:Re-evaluation of the proton affinity of 18-crown-6 using competitive threshold collision-induced dissociation techniques. |
| PubMed:Comparative risk assessment of carcinogens in alcoholic beverages using the margin of exposure approach. |
| PubMed:Structural and energetic effects in the molecular recognition of protonated peptidomimetic bases by 18-crown-6. |
| PubMed:Simultaneous quantitation of 2-acetyl-4-tetrahydroxybutylimidazole, 2- and 4-methylimidazoles, and 5-hydroxymethylfurfural in beverages by ultrahigh-performance liquid chromatography-tandem mass spectrometry. |
| PubMed:Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib. |
| PubMed:Determination of 4(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction. |
| PubMed:Reengineering rate-limiting, millisecond enzyme motions by introduction of an unnatural amino acid. |
| PubMed:Chemical rescue of enzymes: proton transfer in mutants of human carbonic anhydrase II. |
| PubMed:Quantification of 4-methylimidazole in class III and IV caramel colors: validation of a new method based on heart-cutting two-dimensional liquid chromatography (LC-LC). |
| PubMed:Intramolecular proton shuttle supports not only catalytic but also noncatalytic function of carbonic anhydrase II. |
| PubMed:Formation of carcinogenic 4(5)-methylimidazole in Maillard reaction systems. |
| PubMed:Does 4-methylimidazole have tumor preventive activity in the rat? |
| PubMed:Preparation and evaluation of silica-based ionic liquid-modified stationary phase for HPLC. |
| PubMed:Advent of innovative chemiluminescent enzyme immunoassay. |
| PubMed:Ligand effects on the [Cu(PhO)(PhOH)]+ redox active complex. |
| PubMed:DFT calculations of the EPR parameters for Cu(ii) DETA imidazole complexes. |
| PubMed:Effects of 4-methylimidazole on cerebral glutamate decarboxylase activity and specific GABA receptor binding in mice. |
| PubMed:Three-dimensional networks in bis(imidazolium) 2,2'-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate. |
| PubMed:Light-induced oxidation of tryptophan and histidine. Reactivity of aromatic N-heterocycles toward triplet-excited flavins. |
| PubMed:Microfluidic device capable of sensing ultrafast chemiluminescence. |
| PubMed:Comparative analysis of mutant tyrosine kinase chemical rescue. |
| PubMed:A DFT study of the 67Zn, 14N and 2H electric field gradient tensors in Zinc(II)-4-MeIm complexes and extrapolation to superoxide dismutase. |
| PubMed:Reaction dynamics of excited 2-(3-benzoylphenyl)propionic acid (ketoprofen) with histidine. |
| PubMed:Structures of human cytochrome P-450 2E1. Insights into the binding of inhibitors and both small molecular weight and fatty acid substrates. |
| PubMed:Two three-dimensional networks in the binary molecular adducts 4-methylimidazolium hydrogen terephthalate and bis(4-methylimidazolium) terephthalate. |
| PubMed:Hydrogen atom transfer reactions of iron-porphyrin-imidazole complexes as models for histidine-ligated heme reactivity. |
| PubMed:Synthesis of cyclic oligomers from histidine-derived building blocks using dynamic combinatorial chemistry. |
| PubMed:Different protonation equilibria of 4-methylimidazole and acetic acid. |
| PubMed:Binding of antitumor ruthenium complexes to DNA and proteins: a theoretical approach. |
| PubMed:Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice. |
| PubMed:Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344/N rats and B6C3F1 mice (feed studies). |
| PubMed:Location of binding sites in small molecule rescue of human carbonic anhydrase II. |
| PubMed:Supercritical fluid extraction (SFE) of 4(5)-methylimidazole (4-MeI) and 2-acetyl-4(5)-(1,2,3,4)-tetrahydroxybutyl-imidazole (THI) from ground-coffee with high-performance liquid chromatographic-electrospray mass spectrometric quantification (HPLC/ESI-MS). |
| PubMed:Variation of atomic charges on proton transfer in strong hydrogen bonds: the case of anionic and neutral imidazole-acetate complexes. |
| PubMed:Protonation and hydrogen-bonding state of the distal histidine in the CO complex of horseradish peroxidase as studied by ultraviolet resonance Raman spectroscopy. |
| PubMed:Synthesis, reactivity, and X-ray crystal structure of some mixed-ligand oxovanadium(V) complexes: first report of binuclear oxovanadium(V) complexes containing 4,4'-bipyridine type bridge. |
| PubMed:Proton transfer pathways in the mutant His-64-Ala of human carbonic anhydrase II. |
| PubMed:Solid-phase extraction of 4(5)-methylimidazole (4MeI) and 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) from foods and beverages with subsequent liquid chromatographic-electrospray mass spectrometric quantification. |
| PubMed:Inhibitive properties and surface morphology of a group of heterocyclic diazoles as inhibitors for acidic iron corrosion. |
| PubMed:Induction of thyroid lesions in 14-week toxicity studies of 2 and 4-methylimidazole in Fischer 344/N rats and B6C3F1 mice. |
| PubMed:NMR and theoretical study on the coordination and solution structures of the interaction between diperoxovanadate complexes and histidine-like ligands. |
| PubMed:Variation of geometries and electron properties along proton transfer in strong hydrogen-bond complexes. |
| PubMed:Delamination and aromatic amine intercalation of layered aluminophosphate with [Al3P4O16]3- stoichiometry. |
| PubMed:Proton transfer from exogenous donors in catalysis by human carbonic anhydrase II. |
| PubMed:Environmental effects on proton transfer in a strong hydrogen bond dimer: the 4-methyl-imidazole-aspartate case. |
| PubMed:From model compounds to protein binding: syntheses, characterizations and fluorescence studies of [RuII(bipy)(terpy)L]2+ complexes (bipy = 2,2'-bipyridine; terpy = 2,2':6',2''-terpyridine; L = imidazole, pyrazole and derivatives, cytochrome c). |
| PubMed:A strong positive dendritic effect in a peptide dendrimer-catalyzed ester hydrolysis reaction. |
| PubMed:Lead and thallium tetrakis(imidazolyl)borates: modifying structure by varying metal and anion. |
| PubMed:NTP technical report on the toxicity studies of 2- and 4-Methylimidazole (CAS No. 693-98-1 and 822-36-6) administered in feed to F344/N rats and B6C3F1 mice. |
| PubMed:Synthesis and esterolytic activity of catalytic peptide dendrimers. |
| PubMed:An EPR, ESEEM, structural NMR, and DFT study of a synthetic model for the covalently ring-linked tyrosine-histidine structure in the heme-copper oxidases. |
| PubMed:Solvent and pH effects on fast and ultrasensitive 1,1'-oxalyldi(4-methyl)imidazole chemiluminescence. |
| PubMed:Oxovanadium(IV) and -(V) complexes of dithiocarbazate-based tridentate Schiff base ligands: syntheses, structure, and photochemical reactivity of compounds involving imidazole derivatives as coligands. |
| PubMed:Fast peroxyoxalate chemiluminescence for minimized analytical separation systems. |
| PubMed:The refined atomic structure of carbonic anhydrase II at 1.05 A resolution: implications of chemical rescue of proton transfer. |
| PubMed:Gas chromatographic-mass spectrometric quantification of 4-(5-)methylimidazole in roasted coffee after ion-pair extraction. |
| PubMed:Direct infrared detection of the covalently ring linked His-Tyr structure in the active site of the heme-copper oxidases. |
| PubMed:Chemical rescue in catalysis by human carbonic anhydrases II and III. |
| PubMed:Urine markers of interstitial cystitis. |
| PubMed:Structural and kinetic analysis of the chemical rescue of the proton transfer function of carbonic anhydrase II. |
| PubMed:Crystal structure of bis(4-methylimidazole)tetraphenylporphyrinatoiron(III) chloride and related compounds. Correlation of ground state with Fe-N bond lengths. |
| PubMed:The electronic structure and spectra of Ru(II) and Ru(III) complexes with imidazole and its derivatives. |
| PubMed:Kinetic studies of imidazole and its methyl derivative binding to metmyoglobin: effects of substitute methyl on the binding affinity. |
| PubMed:Reactive-site design in folded-polypeptide catalysts--the leaving group pKa of reactive esters sets the stage for cooperativity in nucleophilic and general-acid catalysis. |
| PubMed:Trans-substitution of the proximal hydrogen bond in myoglobin: I. Structural consequences of hydrogen bond deletion. |
| PubMed:Ammoniated forage poisoning: acute toxicity of newly identified dialkylimidazoles to inbred mice. |
| PubMed:The binding of imidazole in an azurin-like blue-copper site. |
| PubMed:Modification of histidine residues by 4,5-epoxy-2-alkenals. |
| PubMed:Proton resonance assignments and ligand exchange kinetics in high-spin and mixed-spin myoglobin complexes using two-dimensional exchange spectroscopy. |
| PubMed:Structural changes in the heme proximal pocket induced by nitric oxide binding to soluble guanylate cyclase. |
| PubMed:Imidazoles suppress rat testosterone secretion and testicular interstitial fluid formation In vivo. |
| PubMed:The regiospecific N-derivatization of histidine side chains: reinvestigation of a supposed N tau to N pi migration. |
| PubMed:Protein modification by a Maillard reaction intermediate methylglyoxal. Immunochemical detection of fluorescent 5-methylimidazolone derivatives in vivo. |
| PubMed:Association of interleukin-6 in the cerebrospinal fluid during crisis of calf with ammoniated feed syndrome. |
| PubMed:Characterization of endothelial nitric-oxide synthase and its reaction with ligand by electron paramagnetic resonance spectroscopy. |
| PubMed:Nonsteric factors dominate binding of nitric oxide, azide, imidazole, cyanide, and fluoride to the rhizobial heme-based oxygen sensor FixL. |
| PubMed:Oxidative transformation of 2-hydroxyestrone. Stability and reactivity of 2,3-estrone quinone and its relationship to estrogen carcinogenicity. |
| PubMed:Modulation of protein function by exogenous ligands in protein cavities: CO binding to a myoglobin cavity mutant containing unnatural proximal ligands. |
| PubMed:Reactions of 3,4-estrone quinone with mimics of amino acid side chains. |
| PubMed:Responses to L-163,491, a nonpeptide angiotensin II mimic, in the pulmonary vascular bed of the cat. |
| PubMed:Structure of metal site in Cd-substituted His117Gly mutant of azurin with and without addition of imidazole derivatives. |
| PubMed:Marked effects of alcohols and imidazoles on the cumyl hydroperoxide reaction with the wild-type cytochrome P450 1A2. |
| PubMed:Toxicokinetics of 4-methylimidazole in the male F344 rat. |
| PubMed:Histidine oxidation in the S2 to S3 transition probed by FTIR difference spectroscopy in the Ca(2+)-depleted photosystem II: comparison with histidine radicals generated by UV irradiation. |
| PubMed:Metabolism-dependent toxicity of methimazole in the olfactory nasal mucosa. |
| PubMed:Inhibition of p-nitrophenol hydroxylase in rat liver microsomes by small aromatic and heterocyclic molecules. |
| PubMed:The pharmacokinetics and metabolism of DuP 532, a non-peptide angiotensin II receptor antagonist, in rats and dogs. |
| PubMed:Disposition of 4-methylimidazole in goats and heifers. |
| PubMed:Further arguments against 4-methylimidazole as causal factor in ammoniated forage toxicosis: experimental seed-hay poisoning in young lambs. |
| PubMed:Molecular changes following oxidoreduction of cytochrome b559 characterized by Fourier transform infrared difference spectroscopy and electron paramagnetic resonance: photooxidation in photosystem II and electrochemistry of isolated cytochrome b559 and iron protoporphyrin IX-bisimidazole model compounds. |
| PubMed:N1-(2-hydroxyethylthioethyl)-4-methyl imidazole (4-met-1-imid-thiodiglycol) in plasma and urine: a novel metabolite following dermal exposure to sulphur mustard. |
| PubMed:Comparison of methods for intestinal histamine application: histamine in enterosoluble capsules or via a duodeno-jenunal tube. Influence of fast and histamine-restrictive diet. |
| PubMed:High-performance liquid chromatographic determination of 4-methylimidazole in sheep plasma and in ammoniated tall fescue hay. |
| PubMed:Pharmacokinetics of 4-methylimidazole in sheep. |
| PubMed:Determination of 4-methylimidazole in caramel color by capillary isotachophoresis. |
| PubMed:Theoretical calculation of tautomer equilibria in solution: 4-(5-)methylimidazole. |
| PubMed:Generation of a catalytic antibody by site-directed mutagenesis. |
| PubMed:Pathology and pathophysiology of painful bladder diseases. |
| PubMed:Uranyl-ion catalyzed oligonucleotide synthesis from adenosine-5'-phosphorazolide. The effect of azoles as nucleotide activating groups. |
| PubMed:Derivatives of epinephrine, norepinephrine, octopamine and histamine formed by homogenates of Trichostrongylus colubriformis, a nematode parasite of ruminants. |
| PubMed:Electron-nuclear coupling in nitrosyl heme proteins and in nitrosyl ferrous and oxy cobaltous tetraphenylporphyrin complexes. |
| PubMed:Effects of 4-methylimidazole in young calves. |
| PubMed:The relationship between uncoupling of oxidative phosphorylation and neuronal necrosis within the CNS in rats dosed with trihalogenated imidazoles. |
| PubMed:Urinary excretion of a metabolite of histamine (1,4-methyl-imidazole-acetic-acid) in painful bladder disease. |
| PubMed:Effects of imidazole and some imidazole-derivatives on lisuride-induced mounting and aggressiveness. |
| PubMed:Etiology of ammoniated hay toxicosis. |
| PubMed:Pilot studies in cattle and mice to determine the presence of 4-methylimidazole in milk after oral ingestion. |
| PubMed:Synthesis and biological activity of 5-thiobredinin and certain related 5-substituted imidazole-4-carboxamide ribonucleosides. |
| PubMed:Inhibition of tolbutamide metabolism by substituted imidazole drugs in vivo: evidence for a structure-activity relationship. |
| PubMed:[Determination of 4-methylimidazole in caramel color by an improved thin-layer chromatography method]. |
| PubMed:A simple and convenient synthesis of 3'-5'- or 2'-5'-linked oligoribonucleotide by polymerization of unprotected ribonucleoside using phosphorus tris-azole. |
| PubMed:The prebiotic synthesis and catalytic role of imidazoles and other condensing agents. |
| PubMed:Characterization of cimetidine, ranitidine, and related structures' interaction with cytochrome P-450. |
| PubMed:Potential Radiosensitizing Agents III: 2-Nitro-4-acetylimidazole analogs. |
| PubMed:Arachidonic acid induces human platelet-fibrin retraction: the role of platelet cyclic endoperoxides. |
| PubMed:Benzoate catalysis in the hydrolysis of endo-5-[4'(5')imidazolyl]-bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate: Implications for the charge-transfer mechanism of catalysis by serine proteases. |
| PubMed:Reactions between peroxidizing lipids and histidyl residue analogues: enhancement of lipid oxidation and browning by 4-methylimidazole. |
| PubMed:Specific modification of 17 beta-estradiol dehydrogenase from human placenta by nicotinamide- (5-bromoacetyl-4-methylimidazole) dinucleotide. |
| PubMed:Quantitative determination of 4-methylimidazole as 1-acetyl derivative in caramel color by gas-liquid chromatography. |
| PubMed:[Synthesis and properties of 5-acetyl-4-methyl-1-(beta-d-ribofuranosyl)-imidazole-5' di-and-triphosphate]. |
| PubMed:[Specific incorporation of the coenzyme analogue nicotinamide-(5-(bromoacetyl)-4-methyl-imidazole)-dinucleotide into alcohol dehydrogenase from liver]. |
| PubMed:Some new derivatives of 4-methylimidazole. |
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3D/inchi