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Sigma-Aldrich

5-(4-Hydroxyphenyl)-5-phenylhydantoin

98%

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Synonym(s):
4-Hydroxydiphenylhydantoin, p-Hydroxyphenytoin, NSC 156081
Empirical Formula (Hill Notation):
C15H12N2O3
CAS Number:
2784-27-2
Molecular Weight:
268.27
EC Number:
220-492-2
MDL number:
MFCD00005262
UNSPSC Code:
12352100
PubChem Substance ID:
24849940
NACRES:
NA.22

Assay

98%

form

solid

mp

>300 °C (lit.)

solubility

soluble 50 mg/mL, clear, colorless to faintly yellow (DMF:MeOH(2:1))

SMILES string

Oc1ccc(cc1)C2(NC(=O)NC2=O)c3ccccc3

InChI

1S/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)

InChI key

XEEDURHPFVXALT-UHFFFAOYSA-N

General description

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

Application

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.
Reactant for activation of hydroxylated metabolites of carbamazepine and phenytoin

Used in studies investigating
Transport across the human placenta barrier
Effects on cellular glucose transport

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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GLC determination of plasma concentration of phenylbutazone and its metabolite oxyphenbutazone.
K K Midha et al.
Journal of pharmaceutical sciences, 63(8), 1234-1239 (1974-08-01)
Vikas Kumar et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(12), 1966-1975 (2006-09-12)
Drug-drug interactions may cause serious adverse events in the clinical setting, and the cytochromes P450 are the enzyme system most often implicated in these interactions. Cytochrome P450 2C is the second most abundant subfamily of cytochrome P450 enzymes and is
Joo-Ho Park et al.
Biotechnology and bioengineering, 78(7), 779-793 (2002-05-10)
We developed a kinetic model that describes a heterogeneous reaction system for the production of D-p-hydroxyphenylglycine from D,L-p-hydroxyphenyl-hydantoin using D-hydantoinase of Bacillus stearothermophilus SD1 and N-carbamoylase of Agrobacterium tumefaciens NRRL B11291. As a biocatalyst, whole cells with separately or co-expressed
Miki Nakajima et al.
Drug metabolism and disposition: the biological fate of chemicals, 30(11), 1250-1256 (2002-10-19)
In humans, orally administered phenytoin, 5,5-diphenylhydantoin, is mainly excreted as 5-(4'-hydroxyphenyl)-5-phenylhydantoin (4'-HPPH) O-glucuronide. Phenytoin is oxidized to 4'-HPPH by CYP2C9 and to a minor extent by CYP2C19, and then 4'-HPPH is metabolized to 4'-HPPH O-glucuronide by UDP-glucuronosyltransferase (UGT). In the
Yu C Kim et al.
Biopharmaceutics & drug disposition, 29(1), 51-61 (2007-11-21)
It has been reported that diabetic patients have an increased risk of developing epileptic convulsions compared with the non-diabetic population, and phenytoin has widely been used for neuralgia in diabetic neuropathy. It has also been reported that in both diabetic
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