144754
4-Phenylimidazole
97%
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About This Item
Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
Molecular Weight:
144.17
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-580-1
Beilstein/REAXYS Number:
2969
MDL number:
Assay:
97%
InChI key
XHLKOHSAWQPOFO-UHFFFAOYSA-N
InChI
1S/C9H8N2/c1-2-4-8(5-3-1)9-6-10-7-11-9/h1-7H,(H,10,11)
SMILES string
c1ccc(cc1)-c2c[nH]cn2
assay
97%
mp
128-131 °C (lit.)
solubility
acetone: soluble 25 mg/mL, clear, colorless to yellow (typical)
functional group
phenyl
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
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 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
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
Y K Li et al.
Biochimica et biophysica acta, 999(3), 227-232 (1989-12-21)
Over 25 nitrogen-containing heterocycles were tested as inhibitors of sweet almond beta-glucosidase (EC 3.2.1.21). Among the most potent of these are some imidazole derivatives. The pH dependence indicates that the unprotonated inhibitor binds most tightly to the catalytically active species
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