2784-27-2

Basic information

• Product Name: 5-(4-HYDROXYPHENYL)-5-PHENYLHYDANTOIN
• Synonyms: (p-hydroxyphenyl)phenylhydantoin;4-hydroxydiphenylhydantoin;4-hydroxyphenytoin;5-(4-hydroxyphenyl)-5-phenyl-4-imidazolidinedione;5-(p-hydroxyphenyl)-5-phenyl-hydantoi;5-(p-hydroxyphenyl)-5-phenylhydantoin;5-p-hydroxyphenyl-5-phenylhydantoin;hydroxydiphenylhydantoin
• CAS NO: 2784-27-2
• Molecular Formula: C₁₅H₁₂N₂O₃
• Molecular Weight: 268.27
• EINECS: 220-492-2
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 2784-27-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 411.43°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.1992 (rough estimate)
• Refractive Index: 1.5906 (estimate)
• Solubility: soluble50mg/mL, clear, colorless to faintly yellow (DMF:MeOH(2:1
• Water Solubility: 36mg/L(37 oC)
• CAS DataBase Reference: 5-(4-HYDROXYPHENYL)-5-PHENYLHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-HYDROXYPHENYL)-5-PHENYLHYDANTOIN(2784-27-2)
• EPA Substance Registry System: 5-(4-HYDROXYPHENYL)-5-PHENYLHYDANTOIN(2784-27-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MU2485000
• Hazardous Substances Data: 2784-27-2(Hazardous Substances Data)

Usage

Uses

5-(4-Hydroxyphenyl)-5-phenylhydantoin was used in enantiomeric separation of chiral pharmaceuticals using a teicoplanin chiral stationary phase by aqueous and non-aqueous packed capillary electrochromatography. It was used as internal standard in determination of phenylbutazone and its metabolite oxyphenbutazone in human plasma by GLC.

Definition

ChEBI: A imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.

General Description

5-(4-Hydroxyphenyl)-5-phenylhydantoin is the major metabolite of phenytoin.

InChI:InChI=1/C15H12N2O3/c18-12-8-6-11(7-9-12)15(10-4-2-1-3-5-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)

Upstream product

• 506-87-6 ammonium carbonate 
• 1137-42-4 4-Hydroxybenzophenone 
• 57-41-0 phenythoin 
• 611-94-9 4-Methoxybenzophenone 
• 151-50-8 potassium cyanide 
• 1066-33-7 ammonium bicarbonate 
• 17816-50-1 5-(4-methoxyphenyl)-5-phenylimidazolidine-2,4-dione 

Downstream Products

• 57496-20-5 4'-(S)-hydroxyphenytoin 

Relevant articles and documents

Stable-isotope methodology for the bioavailability study of phenytoin during multiple-dosing regimens

With the highly sensitive and specific gas chromatography-mass spectrometry (GC-MS), plasma concentrations resulting from an intravenous administration of only a small amount of stable isotopically labeled phenytoin (DPH-d10) were determined to obtain information on the accurate clearance values under steady-state conditions attained with unlabeled phenytoin (DPH-d0). A time course of DPH-d10 concentrations was followed simultaneously with DPH-d0 during dosing intervals by GC-MS, with DPH-d5 as an internal standard. The present stable-isotope methodology offered advantages for the estimation of absolute bioavailability of the oral phenytoin dose in patients, while normal therapy was continued and not withdrawn.

Deracemization of 5-(4-hydroxyphenyl)-5-phenylhydantoin (HPPH): Practical synthesis of (-)-(S)-HPPH

In the presence of 10% NaOH in boiling MeOH enantiomerically enriched HPPH is racemized. This permits the deracemization of HPPH in the presence of brucine, giving enantiomerically pure (-)-(S)-HPPH [(-)-(S)-5-(4-hydroxyphenyl)- 5-phenylhydandoin].

Comparative study on the para-metabolic oxidation of phenytoin and decadeuteriophenytoin

The in-vivo metabolic conversion of equal mixture of phenytoin and decadeuteriophenytoin to the para-hydroxy metabolite in rat was investigated in order to verify a possible role of an insertion or abstraction mechanisms in the hydroxylation process. Determination of k(H)/k2(H) values of urine samples at 2 h intervals for 24 h indicated that there was no isotope effect during in-vivo para-hydroxylation of phenytoin. This gives evidence of the arene oxide intermediacy possibly being the sole pathway for para-hydroxylation of phenytoin.