benzyl 2-[6-(benzyloxy)-3-oxo-3H-xanthen-9-yl]benzoate

• ChemBase ID: 153729
• Molecular Formular: C34H24O5
• Molecular Mass: 512.55136
• Monoisotopic Mass: 512.16237387
• SMILES: c1ccc(cc1)COc1ccc2c(c1)oc1cc(=O)ccc1c2c1ccccc1C(=O)OCc1ccccc1
• Canonical SMILES: O=c1ccc2c(c1)oc1c(c2c2ccccc2C(=O)OCc2ccccc2)ccc(c1)OCc1ccccc1
• InChI: InChI=1S/C34H24O5/c35-25-15-17-29-31(19-25)39-32-20-26(37-21-23-9-3-1-4-10-23)16-18-30(32)33(29)27-13-7-8-14-28(27)34(36)38-22-24-11-5-2-6-12-24/h1-20H,21-22H2
• InChIKey: YZJGKSLPSGPFEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-[6-(benzyloxy)-3-oxo-3H-xanthen-9-yl]benzoate
• IUPAC Traditional name: benzyl 2-[3-(benzyloxy)-6-oxoxanthen-9-yl]benzoate
• Synonyms: DBF; Dibenzylfluorescein

Database IDs

• MDL Number: MFCD13184323
• PubChem SID: 162247868
• PubChem CID: 371436

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 6.9537306
• LogD (pH = 7.4): 6.9537306
• Log P: 6.9537306
• Molar Refractivity: 161.8892 cm^3
• Polarizability: 57.57786 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 7/9-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥99% (H-NMR)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C34H24O5

DETAILS

Sigma Aldrich - D7191

Application
DBF is dealkylated by cytochromes P450 (especially CYP2C8, CYP2C9, CYP2C19, and CYP3A) to form a fluorescein ester. The fluorescent fluorescein product can be quantitated after the addition of base, which hydrolyzes the ester and increases the pH for optimal fluorescein fluorescence detection.