3',6'-bis(acetyloxy)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid

• ChemBase ID: 130825
• Molecular Formular: C25H16O9
• Molecular Mass: 460.38914
• Monoisotopic Mass: 460.07943209
• SMILES: CC(=O)Oc1ccc2c(c1)Oc1cc(ccc1C12c2ccc(cc2C(=O)O1)C(=O)O)OC(=O)C
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)C(=O)O)ccc(c1)OC(=O)C
• InChI: InChI=1S/C25H16O9/c1-12(26)31-15-4-7-19-21(10-15)33-22-11-16(32-13(2)27)5-8-20(22)25(19)18-6-3-14(23(28)29)9-17(18)24(30)34-25/h3-11H,1-2H3,(H,28,29)
• InChIKey: WPUZGNPQMIWOHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-bis(acetyloxy)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• IUPAC Traditional name: 3',6'-bis(acetyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• Synonyms: 3',6'-Bis(acetyloxy)-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic Acid; 5-Carboxyfluorescein Diacetate; 5-CFDA; 5-Carboxy-di-O-acetylfluorescein; 5-Carboxyfluorescein diacetate

Database IDs

• CAS Number: 79955-27-4
• MDL Number: MFCD00036872
• Beilstein Number: 68265
• PubChem SID: 24873962; 162225103; 24892738
• PubChem CID: 133314

CALCULATED PROPERTIES

• Acid pKa: 3.8326921
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.6889514
• LogD (pH = 7.4): 0.112514965
• Log P: 3.3595784
• Molar Refractivity: 116.7793 cm^3
• Polarizability: 44.47819 Å^3
• Polar Surface Area: 125.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Fluorescence: λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0 (after cleavage by esterase)(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (HPLC); ≥95.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C25H16O9

DETAILS

Toronto Research Chemicals - C178345

5-Carboxyfluorescein diacetate is used in the synthesis of Rhodamines.

REFERENCES

• Hug, H., et al.: Biochemistry, 38, 13906 (1999)
• Shibata, A., et al.: Bioorg. Med. Chem. Lett., 18, 2246 (1999)
• Puliti, D., et al.: Bioorg. Med. Chem., 19, 1023 (1999)