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

• ChemBase ID: 126421
• Molecular Formular: C21H12O7
• Molecular Mass: 376.31578
• Monoisotopic Mass: 376.05830272
• SMILES: c1cc2c(cc1C(=O)O)C1(c3ccc(cc3Oc3c1ccc(c3)O)O)OC2=O
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cc(cc2)C(=O)O)ccc(c1)O
• InChI: InChI=1S/C21H12O7/c22-11-2-5-14-17(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/h1-9,22-23H,(H,24,25)
• InChIKey: BZTDTCNHAFUJOG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid
• IUPAC Traditional name: carboxyfluorescein
• Synonyms: 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic Acid; (3,6,9-Trihydroxyxanthen-9-yl)terephthalic Acid; 6-Carboxyfluorescein; 6-FAM; Carboxyfluorescein; FLUOS; 6-Carboxyfluorescein

Database IDs

• CAS Number: 3301-79-9
• MDL Number: MFCD00036873
• Beilstein Number: 54341
• PubChem SID: 162220755; 24892266
• PubChem CID: 76806
• CHEBI ID: 39073
• Chemspider ID: 69262
• Wikipedia Title: Carboxyfluorescein

CALCULATED PROPERTIES

• Acid pKa: 3.542912
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.5872847
• LogD (pH = 7.4): 0.15534905
• Log P: 3.5379257
• Molar Refractivity: 98.4763 cm^3
• Polarizability: 36.78754 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; DMSO: soluble; H2O: soluble (pH ≥ 5); Methanol
• Apperance: Orange Solid
• Melting Point: >300 °C(lit.); >300°C
• Absorption Wavelength: λmax 492 nm, 0.1 N in NaOH
• Fluorescence: λex 492 nm; λem 517 nm (pH 8.0); λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~97% (HPLC); ≥95% (HPLC); 95+%
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C21H12O7

DETAILS

Sigma Aldrich - C0662

Application
Fluorescent dye.
包装
50 mg in poly bottle

Sigma Aldrich - 54115

Application
Fluorescent dye.

Toronto Research Chemicals - C178325

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)