ethyl 1-benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate

• ChemBase ID: 53850
• Molecular Formular: C14H15NO4
• Molecular Mass: 261.2732
• Monoisotopic Mass: 261.10010797
• SMILES: C1(=C(CN(C1=O)Cc1ccccc1)C(=O)OCC)O
• Canonical SMILES: CCOC(=O)C1=C(O)C(=O)N(C1)Cc1ccccc1
• InChI: InChI=1S/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,16H,2,8-9H2,1H3
• InChIKey: IGYRPDIWSYGHMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• IUPAC Traditional name: ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylate
• Synonyms: 1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester; 1-Benzyl-4-bydroxy-5-oxo-3-pyrroline-3-carboxylic Acid Ethyl Ester; NSC 229530; EBPC; 2,5-Dihydro-4-hydroxy-5-oxo-1-(phenylmethyl)-1H-pyrrole-3-carboxylic acid ethyl ester; CP-10668; EBPC

Database IDs

• CAS Number: 4450-98-0
• MDL Number: MFCD00179167
• PubChem SID: 162058613
• PubChem CID: 54677973

CALCULATED PROPERTIES

• Acid pKa: 6.437804
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1272856
• LogD (pH = 7.4): 0.16871071
• Log P: 1.1747024
• Molar Refractivity: 70.1908 cm^3
• Polarizability: 26.70844 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥10 mg/mL; Methanol
• Apperance: Pale Pink Solid; white powder
• Melting Point: 132-134°C

Safety Information

• Storage Condition: protect from light; Refrigerator
• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C14H15NO4

DETAILS

Sigma Aldrich - PZ0140

Biochem/physiol Actions
EBPC is an aldose reductase inhibitor; anti-cancer.
Other Notes
air sensitive
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - E320500

A highly specific aldose reductase inhibitor that has been shown to enhance HeLa cell sensitivity to chemotherapeutic drugs.

REFERENCES

• Mylari, B.L. et al.: J. Med. Chem., 34, 1011 (1991)
• Lee, E. et al.: Anti-Cancer Drugs, 13, 859 (1991)
• Verma, M. et al.: Eur. J. Pharmacol., 584, 213 (1991)