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I5513

Sigma-Aldrich

Imidazole

for molecular biology, ≥99% (titration)

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Synonym(s):
3-Azapyrrole, 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

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

application(s)

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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Imidazole for molecular biology, &#8805;99% (titration)

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Imidazole for molecular biology, &#8805;99% (titration), free-flowing, Redi-Dri&#8482;

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RDD039

Imidazole

-
assay

≥99% (titration)

assay

≥99.5% (GC)

assay

≥99% (titration)

assay

≥99% (titration)

form

crystalline powder

form

powder or crystals

form

-

form

crystalline powder

pH

6.2-7.8 (25 °C)

pH

9.5-11.0 (25 °C, 0.1 M in H2O)

pH

9.5-11.0 (25 °C, 5% in H2O)

pH

6.2-7.8 (25 °C)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

mp

88-91 °C (lit.)

solubility

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

solubility

H2O: 0.1 M at 20 °C, clear, colorless

solubility

-

solubility

-

General description

Imidazole, also known as Glyoxalin, is an aromatic heterocyclic diazole and a key biological buffer with a pH range of 6.2 to 7.8 at 25°C. It has a wide range of applications in molecular biology, biochemistry, and proteomics. In proteomics, imidazole is essential for eluting histidine-tagged proteins from IMAC columns. It is a strong chelator of divalent cations, such as nickel and zinc, which disrupts the interaction between the His-tag and the metal ions. This allows for the efficient elution of purified proteins.

Furthermore, imidazole is indispensable for enhancing protein purity. It is widely used in preparing buffer solutions optimized for downstream purification columns. Imidazole solutions are also effective elution and washing agents throughout protein purification processes. Additionally, imidazole can be used for assays of horseradish peroxidase (HRP) and reverse staining of SDS-PAGE gels for protein detection. Imidazole is a versatile and valuable reagent for a wide range of biological applications. It is an essential component of many buffers and is also used in protein purification and detection protocols.

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
  • as a binding buffer, wash buffer, and elution buffer in a study involving protein expression and purification of bioactive growth factors for use in cell culture and cellular agriculture
Excellent for buffers in the range of pH 6.2-7.8

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).

Features and Benefits

  • Suitable for Molecular Biology and Biochemical Research
  • Can be used as a Buffer component, for Protein separation
  • Free from DNase, NICKase, RNase, and Protease
  • Effective Buffering from pH 6.2 to 7.8 (25 °C) with a pKa of 6.9 (25 °C)

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

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

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Protein expression and purification of bioactive growth factors for use in cell culture and cellular agriculture
Semper C et al.
STAR protocols, 4, 102351-102351 (2023)
Isolation of Phagosomes from Dendritic Cells by Using Magnetic Beads
Manoury B
Bio-protocol, 3(14), 177-184 (2013)
[Purification of proteins using polyhistidine affinity tags
Bornhorst JA and Falke JJ
Methods in Enzymology, 326, 245-254 (2000)
Molecular pathways regulating pro-migratory effects of Hedgehog signaling
Hochman E, et al.
The Journal of Biological Chemistry, 281(45), 33860-33870 (2006)
Imidazoles as potential anticancer agents
Ali I, et al.
MedChemComm, 8(9), 1742-1773 (2017)

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