3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid; 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid

• ChemBase ID: 104167
• Molecular Formular: C42H24O14
• Molecular Mass: 752.63156
• Monoisotopic Mass: 752.11660545
• SMILES: OC(=O)c1cc2c(cc1)C1(OC2=O)c2ccc(O)cc2Oc2c1ccc(O)c2.OC(=O)c1cc2c(cc1)C(=O)OC12c2ccc(O)cc2Oc2c1ccc(O)c2
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)C(=O)O)ccc(c1)O.Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cc(cc2)C(=O)O)ccc(c1)O
• InChI: InChI=1S/2C21H12O7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)21(15)14-4-1-10(19(24)25)7-13(14)20(26)28-21;22-11-2-5-14-17(8-11)27-18-9-12(23)3-6-15(18)21(14)16-7-10(19(24)25)1-4-13(16)20(26)28-21/h2*1-9,22-23H,(H,24,25)
• InChIKey: BPVHBBXCESDRKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid; 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid
• IUPAC Traditional name: 5-carboxyfluorescein; carboxyfluorescein
• Synonyms: 5(6)-Carboxyfluorescein; 4(5)-Carboxyfluorescein; 5(6)-Carboxyfluorescein, mixture of isomers; 5(6)-CARBOXYFLUORESCEIN; 5-(6)-羧酸荧光素,异构体混合物

Database IDs

• CAS Number: 72088-94-9; 76823-03-5
• EC Number: 276-331-1
• MDL Number: MFCD00151081
• PubChem SID: 162091693
• PubChem CID: 44119975

CALCULATED PROPERTIES

• Acid pKa: 3.8326864
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.8670381
• LogD (pH = 7.4): 0.27040523
• Log P: 3.5379257
• Molar Refractivity: 98.4763 cm^3
• Polarizability: 36.786808 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 275 °C (dec.)(lit.); ca 300°C
• Absorption Wavelength: λmax 492 nm
• Fluorescence: λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95% (HPLC); 97%; 99%
• Compostion: Dye content, 90%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C21H12O7

DETAILS

MP Biomedicals - 02154938

Mixed isomers. Purity: 99% A probe for liposome-cell interactions

Sigma Aldrich - 21877

Other Notes
A probe of intracellular pH1,2

Sigma Aldrich - 447293

Packaging
1, 5 g in glass bottle

REFERENCES

• Ralston, E., et al., Biochim. Biophys. Acta, 649: 133, (1981).
• Used as a probe of intracellular pH: Anal. Biochem ., 156, 202 (1986)