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About This Item
Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
Molecular Weight:
144.17
Beilstein:
2969
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
97%
mp
128-131 °C (lit.)
solubility
acetone: soluble 25 mg/mL, clear, colorless to yellow (typical)
functional group
phenyl
SMILES string
c1ccc(cc1)-c2c[nH]cn2
InChI
1S/C9H8N2/c1-2-4-8(5-3-1)9-6-10-7-11-9/h1-7H,(H,10,11)
InChI key
XHLKOHSAWQPOFO-UHFFFAOYSA-N
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Application
4-Phenylimidazole was used to investigate the protein-ligand interactions in cytochrome P450 from the thermoacidophile Picrophilus torridus. It was used as heme ligand during the crystallization of recombinant human indoleamine 2,3-dioxygenase. It was used in the synthesis of complexes of copper and cobalt.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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J K Yano et al.
The Journal of biological chemistry, 275(40), 31086-31092 (2000-06-22)
The structure of the first P450 identified in Archaea, CYP119 from Sulfolobus solfataricus, has been solved in two different crystal forms that differ by the ligand (imidazole or 4-phenylimidazole) coordinated to the heme iron. A comparison of the two structures
M Sono et al.
Biochemistry, 28(13), 5392-5399 (1989-06-27)
The effects of norharman, one of the few known inhibitors of the heme protein indoleamine 2,3-dioxygenase, and of 4-phenylimidazole (4-PheImid), a heme ligand, on the catalytic (Vmax, Km) and spectroscopic properties (optical absorption, CD, and magnetic CD) of the rabbit
Spectral and metabolic properties of liver microsomes from imidazole-pretreated rabbits.
K K Hajek et al.
Biochemical and biophysical research communications, 108(2), 664-672 (1982-09-30)
M Spatzenegger et al.
Molecular pharmacology, 59(3), 475-484 (2001-02-17)
The molecular basis for reversible inhibition of rabbit CYP2B4 and CYP2B5 and rat CYP2B1 by phenylimidazoles was assessed with active-site mutants and new three-dimensional models based on the crystal structure of CYP2C5. 4-Phenylimidazole was 17- to 32-fold more potent toward
Y K Li et al.
Journal of biochemistry, 123(3), 416-422 (1998-05-30)
Series of 4-arylimidazoles, omega-N-acylhistamines and 4-(omega-phenylalkyl)imidazoles were synthesized in order to probe the active site topology of sweet almond beta-glucosidase. These imidazole derivatives were shown to be very powerful competitive inhibitors. Among the 20 tested compounds, omega-N-benzoylhistamine and 4-(3'-phenylpropyl)imidazole are
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