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I5513

Sigma-Aldrich

Imidazole

for molecular biology, ≥99% (titration)

Synonym(s):
1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
Empirical Formula (Hill Notation):
C3H4N2
CAS Number:
Molecular Weight:
68.08
Beilstein:
103853
EC Number:
MDL number:
eCl@ss:
39161001
PubChem Substance ID:
NACRES:
NA.25

Quality Level

grade

for molecular biology

vapor pressure

<1 mmHg ( 20 °C)

assay

≥99% (titration)

form

crystalline powder

pH

6.2-7.8 (25 °C)

pKa (25 °C)

6.95

bp

256 °C (lit.)

mp

88-91 °C (lit.)

solubility

water: 500 mg/mL, clear, colorless to very faintly yellow

Featured Industry

Diagnostic Assay Manufacturing

foreign activity

DNase, RNase and protease, none detected

storage temp.

room temp

SMILES string

c1c[nH]cn1

InChI

1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

InChI key

RAXXELZNTBOGNW-UHFFFAOYSA-N

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General description

Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.

Application

Imidazole has been used
  • in the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein
  • in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography
  • as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells

Excellent for buffers in the range of pH 6.2-7.8

Packaging

5, 25, 100 g in glass bottle

Biochem/physiol Actions

Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division. It also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1C

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 2

Flash Point(F)

293.0 °F - closed cup

Flash Point(C)

145 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Imidazoles as potential anticancer agents
Ali I, et al.
MedChemComm, 8(9), 1742-1773 (2017)
Functional expression of novel human and murine AKR1B genes
Salabei JK, et al.
Chemico-Biological Interactions, 191(1-3), 177-184 (2011)
Imidazole: Having versatile biological activities
Verma A, et al.
Journal of Chemistry, 2013 (2013)
[Purification of proteins using polyhistidine affinity tags
Bornhorst JA and Falke JJ
Methods in Enzymology, 326, 245-254 (2000)
Isolation of Phagosomes from Dendritic Cells by Using Magnetic Beads
Manoury B
Bio-protocol, 3(14), 177-184 (2013)

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