Record Information
Version1.0
Creation date2015-10-09 22:31:12 UTC
Update date2017-01-19 02:36:27 UTC
FoodComEx IDPC000530
FoodDB RecordFDB012307
Chemical Information
NameImidazole
DescriptionIsolated from the seeds of Lens culinaris (lentil)and is also present in the seeds of other legumes: Macrotyloma uniflorum (horse gram), Psophocarpus tetragonolobus (winged bean), Vigna radiata (mung bean) Imidazole is a 5-membered planar ring, which is soluble in water and other polar solvents. It exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms. Imidazole is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water. The compound is classified as aromatic due to the presence of a sextet of ?-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring.; Imidazole is a heterocyclic aromatic organic compound. It is further classified as an alkaloid. Imidazole refers to the parent compound C3H4N2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin.; Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is classified as an alkaloid. Imidazole refers to the parent compound whereas imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine, and the related hormone histamine. Imidazole can serve as a base and as a weak acid. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole.; Imidazole is incorporated into many important biological molecules. The most pervasive is the amino acid histidine, which has an imidazole side chain. Histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin. Histidine can be decarboxylated to histamine, which is also a common biological compound. It is a component of the toxin that causes urticaria, which is another name for allergic hives. The relationship between histidine and histamine are shown below:; This is a general method which is able to give good yields for substituted imidazoles. It is essentially an adaptation of the Debus method called the Debus-Radziszewski imidazole synthesis. The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt. Imidazole is found in pulses.
CAS Number288-32-4
Structure
Thumb
Synonyms
SynonymSource
{Pyrro[b]monazole}HMDB
1,3-Diaza-2,4-cyclopentadienebiospider
1,3-Diaza-2,4-cyclopentadiene-biospider
1,3-Diazoledb_source
1467-16-9 (mono-hydrochloride)biospider
1H-Imidazolebiospider
1H-Imidazole (9CI)biospider
Formamidine, n,n'-vinylene-biospider
Glioksalbiospider
Glyoxalinbiospider
Glyoxalinedb_source
HIMbiospider
IMDbiospider
Imidazolbiospider
Imidazole (8CI)biospider
Imidazole-ringbiospider
Iminazoledb_source
Imutexbiospider
Methanimidamide, N,N'-1, 2-ethenediyl-biospider
Methanimidamide, N,N'-1,2-ethenediyl-biospider
Miazolebiospider
N,N'-1,2-ethenediylmethanimidamidebiospider
N,n'-vinyleneformamidinebiospider
Pyrro(b)monazolebiospider
Pyrro[b]monazolebiospider
Chemical FormulaC3H4N2
IUPAC name1H-imidazole
InChI IdentifierInChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
InChI KeyRAXXELZNTBOGNW-UHFFFAOYSA-N
Isomeric SMILESN1C=CN=C1
Average Molecular Weight68.0773
Monoisotopic Molecular Weight68.037448138
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.08HANSCH,C ET AL. (1995)
Experimental Water SolubilityNot Available
Melting PointMp 88-90°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci D070
AKSci J70047
Glentham GB9580
MetaSci HMDB0001525
Sigma-Aldrich HMDB0001525
Toronto Research Chemicals I350200