5-(4-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

• ChemBase ID: 148107
• Molecular Formular: C15H12N2O3
• Molecular Mass: 268.26738
• Monoisotopic Mass: 268.08479225
• SMILES: c1ccc(cc1)C1(C(=O)NC(=O)N1)c1ccc(cc1)O
• Canonical SMILES: O=C1NC(=O)C(N1)(c1ccc(cc1)O)c1ccccc1
• InChI: 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)
• InChIKey: XEEDURHPFVXALT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: hydroxyphenytoin
• Synonyms: 4-Hydroxydiphenylhydantoin; p-Hydroxyphenytoin; NSC 156081; 5-(4-Hydroxyphenyl)-5-phenylhydantoin; 5-(4-羟基苯基)-5-苯基乙内酰脲

Database IDs

• CAS Number: 2784-27-2
• EC Number: 220-492-2
• MDL Number: MFCD00005262
• PubChem SID: 24849940; 162242284
• PubChem CID: 17732

CALCULATED PROPERTIES

• Acid pKa: 9.156863
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.8442602
• LogD (pH = 7.4): 1.836854
• Log P: 1.8443551
• Molar Refractivity: 72.1632 cm^3
• Polarizability: 27.738516 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.)

Safety Information

• RTECS: MU2485000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C15H12N2O3

DETAILS

Sigma Aldrich - 161543

Packaging
1, 5 g in glass bottle
Application
Reactant for activation of hydroxylated metabolites of carbamazepine and phenytoin1Used in studies investigating Transport across the human placenta barrier2 Effects on cellular glucose transport3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 161543.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.