1-{3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 153939
• Molecular Formular: C24H13NO7
• Molecular Mass: 427.36252
• Monoisotopic Mass: 427.06920176
• SMILES: c1cc2c(cc1N1C(=O)C=CC1=O)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)N2C(=O)C=CC2=O)ccc(c1)O
• InChI: InChI=1S/C24H13NO7/c26-13-2-5-17-19(10-13)31-20-11-14(27)3-6-18(20)24(17)16-4-1-12(9-15(16)23(30)32-24)25-21(28)7-8-22(25)29/h1-11,26-27H
• InChIKey: AYDAHOIUHVUJHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-{3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl}pyrrole-2,5-dione
• Synonyms: 5-Maleimido-fluorescein; N-(5-Fluoresceinyl)maleimide; 1-(3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)-1H-pyrrole-2,5-dione; Fluorescein 5-Maleimide

Database IDs

• CAS Number: 75350-46-8
• MDL Number: MFCD00077345
• PubChem SID: 162248078
• PubChem CID: 122038

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.1525671
• LogD (pH = 7.4): 3.1323714
• Log P: 3.1528287
• Molar Refractivity: 113.1878 cm^3
• Polarizability: 42.116077 Å^3
• Polar Surface Area: 113.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Orange to Brown Solid
• Melting Point: >275°C (dec.)
• Fluorescence: λex 492 nm; λem 518 nm in 0.1 M Tris pH 9.0, 2-mercaptoethanol

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥90% (HPLC)
• Suitability: corresponds for coupling to thiols; suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C24H13NO7

DETAILS

Toronto Research Chemicals - F489500

Fluorescent labeling reagent for proteins and peptides.

REFERENCES

• Vives, E. and Lebleu, B. : Tetrahedron Letters, 44, 5389 (2003)
• Li, J., et al.: Bioorg. Med. Chem. Lett., 15, 5558 (2003)
• Oejmeyr, L., et al.: Biochemi., 48, 2173 (2003)