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161543

Sigma-Aldrich

5-(4-Hydroxyphenyl)-5-phenylhydantoin

98%

Synonym(s):

4-Hydroxydiphenylhydantoin, p-Hydroxyphenytoin, NSC 156081

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About This Item

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))

functional group

phenyl

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
8214KL
3702HE
00213DG

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Upendra A Argikar et al.
Epilepsy research, 71(1), 54-63 (2006-07-04)
Phenytoin (PHT) is primarily metabolized to 5-(4'-hydroxyphenyl)-5-phenylhydantoin (p-HPPH), accounting for 67-88% of an administered dose in humans. p-HPPH is formed by the cytochrome (CYP) 450 enzymes CYP2C9 and CYP2C19, then glucuronidated and excreted into the urine. CYP2C9 catalyses the prochiral
F Jabbaribar et al.
Journal of chromatographic science, 47(10), 877-880 (2009-11-26)
Determination of phenytoin in biological fluids is necessary due to its non-linear pharmacokinetics and narrow therapeutic index. A simple and rapid micellar electrokinetic chromatographic method was developed for simultaneous determination of phenytoin and its main metabolite, 5-(4-hydroxyphenyl)-5-phenylhydantoin, in human serum.
A Takahashi et al.
Japanese journal of pharmacology, 82(1), 82-84 (2000-06-30)
The effects of phenytoin and its major metabolite, 5-(4-hydroxyphenyl)-5-phenylhydantoin (HPPH), on bone resorption of neonatal mouse calvaria were examined in vitro. Both phenytoin and HPPH induced significant bone resorption as compared to the controls after 72 h in culture. This
Phenytoin overview--metabolite interference in some immunoassays could be clinically important.
William L Roberts et al.
Archives of pathology & laboratory medicine, 128(7), 734-734 (2004-07-02)
C Karlsson et al.
Journal of chromatography. A, 897(1-2), 349-363 (2000-12-29)
Enantiomeric separation of chiral pharmaceuticals is carried out in aqueous and non-aqueous packed capillary electrochromatography (CEC) using a teicoplanin chiral stationary phase (CSP). Capillaries were slurry packed with 5 microm 100-A porous silica particles modified with teicoplanin and initially evaluated
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