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144754

Sigma-Aldrich

4-Phenylimidazole

97%

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$128.00
10 G
$133.00

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5 G
$128.00
10 G
$133.00

About This Item

Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
Molecular Weight:
144.17
Beilstein/REAXYS Number:
2969
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

$128.00


Available to ship onMay 02, 2025Details


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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[1]. It was used as heme ligand during the crystallization of recombinant human indoleamine 2,3-dioxygenase[2]. It was used in the synthesis of complexes of copper and cobalt[3].

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signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Winny W Ho et al.
Biochemistry, 47(7), 2071-2079 (2008-01-17)
The crystal structure of a cytochrome P450 from the thermoacidophile Picrophilus torridus, CYP231A2 (PTO1399), has been solved. This structure reveals a wide open substrate access channel. To better understand ligand-induced structural transitions in CYP231A2, protein-ligand interactions were investigated using 4-phenylimidazole.
T Kimura et al.
Journal of medicinal chemistry, 36(11), 1641-1653 (1993-05-28)
In our continuing search to find systemically bioavailable ACAT (acyl-CoA:cholesterol O-acyltransferase) inhibitors with more potent antiatherosclerotic effect than N-[2-(dimethylamino)-6-[3-(5-methyl-4-phenyl-1H-imidazol-1-yl)propoxy] phenyl]-N'-pentylurea (3), a series of phenylureas linked to 4-phenylimidazole were synthesized and evaluated for in vitro inhibitory activity toward both aortic
X-RAY STUDIES AND ANTIBACTERIAL ACTIVITY IN COPPER AND COBALT COMPLEXES WITH IMIDAZOLE DERIVATIVE LIGANDS.
ATRIA a, et al.
Journal of the Chilean Chemical Society, 56(3), 786-792 (2011)
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

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