4-methyl imidazole
imidazole, 4-methyl-
Identification
| Name | 4-methyl imidazole |
| IUPAC | 5-methyl-1H-imidazole |
| CAS Number | 822-36-6 |
| EINECS | 212-497-3 |
| FDA UNII | Q64GF9FV4I |
| Molecular Formula | C4 H6 N2 |
| Molecular Weight | 82.10582000 |
| MDL Number | MFCD00005201 |
| Nikkaji Number | J43.099D |
| Beilstein | 0001453 |
| XlogP3 | 0.20 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 56.00 °C. @ 760.00 mm Hg |
| Boiling Point | 263.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.007000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 230.00 °F. TCC ( > 110.00 °C. ) |
| logP (o/w) | 0.230 |
| Soluble in | water, 8.246e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-chicken LD50 210 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']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 4-methyl imidazole usage levels up to | not for fragrance use. |
| Recommendation for 4-methyl imidazole flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
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
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.