3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one; acetic acid

• ChemBase ID: 163744
• Molecular Formular: C22H16O7
• Molecular Mass: 392.35824
• Monoisotopic Mass: 392.08960285
• SMILES: c1cc(cc2c1C1(c3c(O2)cc(cc3)O)c2c(C(=O)O1)cccc2)O.CC(=O)O
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)O.CC(=O)O
• InChI: InChI=1S/C20H12O5.C2H4O2/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20;1-2(3)4/h1-10,21-22H;1H3,(H,3,4)
• InChIKey: CPRVUBZYHZGASQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one; acetic acid
• IUPAC Traditional name: acetic acid; fluorescein
• Synonyms: 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-ar-carboxylic Acid; Fluoresceincarboxylic Acid; 5(6)-Carboxyfluorescein

Database IDs

• CAS Number: 72088-94-9
• PubChem SID: 162257879
• PubChem CID: 2734982

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8800821
• LogD (pH = 7.4): 3.8598857
• Log P: 3.8803427
• Molar Refractivity: 91.2201 cm^3
• Polarizability: 34.4024 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Dark-Orange to Brown Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C178315

A useful reagent for the preparation of hydrolytically stable fluorescent conjugates and is a useful starting material for the synthesis of other fluorescein-derives reagent.

REFERENCES

• Theisen, P., et al.: Tetrahedron Lett., 33, 5033 (1992)
• Mattingly, P.: Bioconjgate Chem., 3, 430 (1992, Bertrand, R., et al.: Biochemistry, 34, 9500 (1995)