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

• ChemBase ID: 132710
• Molecular Formular: C25H16O9
• Molecular Mass: 460.38914
• Monoisotopic Mass: 460.07943209
• SMILES: CC(=O)Oc1ccc2c(c1)Oc1cc(ccc1C12c2cc(ccc2C(=O)O1)C(=O)O)OC(=O)C
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cc(cc2)C(=O)O)ccc(c1)OC(=O)C
• InChI: InChI=1S/C25H16O9/c1-12(26)31-15-4-7-18-21(10-15)33-22-11-16(32-13(2)27)5-8-19(22)25(18)20-9-14(23(28)29)3-6-17(20)24(30)34-25/h3-11H,1-2H3,(H,28,29)
• InChIKey: QMOGCCYGOPYYNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 3348-03-6
• MDL Number: MFCD00036871
• Beilstein Number: 67043
• PubChem SID: 162226987; 24892748; 24851718
• PubChem CID: 151095

CALCULATED PROPERTIES

• Acid pKa: 3.5429149
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.4091979
• LogD (pH = 7.4): -0.002541239
• Log P: 3.3595784
• Molar Refractivity: 116.7793 cm^3
• Polarizability: 44.47892 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)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (HPLC); ≥90.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C25H16O9

DETAILS

Sigma Aldrich - C5041

Application
Used to differentiate viable cells from apoptotic cells. Live cells that are not apoptotic accumulate 6-carboxyfluorescein but do not accumulate annexin. Fluorescent wavelengths λex 492 nm; λemm 517 nm in 0.1 M Tris, pH 8.0.

Sigma Aldrich - 19586

Other Notes
Substrate for the assay of cellular esterases1; Flow cytometric assessment of viability of bacteria2,3