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

• ChemBase ID: 130878
• Molecular Formular: C21H12O7
• Molecular Mass: 376.31578
• Monoisotopic Mass: 376.05830272
• SMILES: c1cc2c(cc1C(=O)O)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)C(=O)O)ccc(c1)O
• InChI: InChI=1S/C21H12O7/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/h1-9,22-23H,(H,24,25)
• InChIKey: NJYVEMPWNAYQQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• IUPAC Traditional name: 5-carboxyfluorescein
• Synonyms: 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic Acid; 5-Carboxyfluorescein; 5-FAM; 5-Carboxyfluorescein

Database IDs

• CAS Number: 76823-03-5
• MDL Number: MFCD00036874
• Beilstein Number: 57037
• PubChem SID: 24892258; 162225156; 24888769
• PubChem CID: 123755

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: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO; DMSO: soluble; H2O: soluble; Methanol
• Apperance: Orange Solid
• Melting Point: >300°C
• Fluorescence: λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0

Safety Information

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

Product Information

• Purity: ≥95% (HPLC); 99% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C21H12O7

DETAILS

Sigma Aldrich - 86826

Other Notes
Derivative of fluorescein giving stable derivative upon conjugation with biopolymers1,2

Toronto Research Chemicals - C178320

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)