disodium 3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)

• ChemBase ID: 158115
• Molecular Formular: C20H10Na2O5
• Molecular Mass: 376.26994
• Monoisotopic Mass: 376.03236198
• SMILES: c1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)[O-])[O-].[Na+].[Na+]
• Canonical SMILES: [O-]c1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)[O-].[Na+].[Na+]
• InChI: InChI=1S/C20H12O5.2Na/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;;/h1-10,21-22H;;/q;2*+1/p-2
• InChIKey: RGPLGPBQJOQFJS-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)
• IUPAC Traditional name: disodium 3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-bis(olate)
• Synonyms: C.I. 45350; Fluorescein disodium salt hydrate; NaFl; NaFluo; Sodium fluorescein; Acid Yellow 73; Uranine; Fluorescein sodium salt; 荧光素二钠 水合物; 荧光素钠; 酸性黄 73; 荧光素 钠盐

Database IDs

• CAS Number: 518-47-8
• EC Number: 208-253-0
• MDL Number: MFCD00167039
• Beilstein Number: 3833041
• Merck Index: 144159
• PubChem SID: 24857309; 24894907; 162252251
• PubChem CID: 9885981
• Color Index Number: 45350

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.8800821
• LogD (pH = 7.4): 3.8598857
• Log P: 3.8803427
• Molar Refractivity: 112.3207 cm^3
• Polarizability: 33.875553 Å^3
• Polar Surface Area: 81.65 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >250°C
• Fluorescence: λex 460 nm; λem 515 nm(lit.)

Safety Information

• RTECS: LM5425000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98.5-100.5%; 98.5-100.5% (calc. on dry substance)
• Grade: indicator; JIS special grade; SAJ first grade
• Suitability: complies for TLC
• Antion Traces: chloride (Cl-): ≤3500 mg/kg; sulfate (SO42-): ≤1.2%
• Loss on Drying: ≤10% loss on drying, 105 °C
• Empirical Formula (Hill Notation): C20H10Na2O5

DETAILS

Sigma Aldrich - 28803

General description
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Sigma Aldrich - F6377

Packaging
100, 500 g in glass bottle
Application
Water soluble fluorescent dye used in permeability and vascular perfusion studies due to its small molecular radius.1 Sodium fluorescein is used as a fluorescent tracer to study blood-brain barrier (BBB) and blood-spinal cord barrier (BSCB) permeability in rodent models.2,3,4 The dye was used as a probe substrate in the study of organic anion transporting polypeptide (OATP) mediated drug transport in hepatocytes.5 Sodium fluorescein was also used to monitor in situ solute transportation into bone through fluorescence recovery after photobleaching (FRAP).6

REFERENCES

• Water-soluble form of fluorescein.