2,5-dioxopyrrolidin-1-yl 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylate

• ChemBase ID: 126420
• Molecular Formular: C25H15NO9
• Molecular Mass: 473.3879
• Monoisotopic Mass: 473.07468107
• SMILES: O=C1c2c(cc(C(=O)ON3C(=O)CCC3=O)cc2)C2(O1)c1c(cc(O)cc1)Oc1cc(O)ccc21
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cc(cc2)C(=O)ON2C(=O)CCC2=O)ccc(c1)O
• InChI: InChI=1S/C25H15NO9/c27-13-2-5-16-19(10-13)33-20-11-14(28)3-6-17(20)25(16)18-9-12(1-4-15(18)24(32)34-25)23(31)35-26-21(29)7-8-22(26)30/h1-6,9-11,27-28H,7-8H2
• InChIKey: VDABVNMGKGUPEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-6-carboxylate
• Synonyms: 6-Carboxyfluorescein-NHS; 6-Carboxyfluorescein-N-succinimidyl Ester; 1-[[3’,6’-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9’-[9H]xanthen]-6-yl]carbonyl]oxy]-2,5-pyrrolidinedione; Fluorescein-6-carboxylic Acid N-Succinimidyl Ester; 3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; 6-Carboxyfluorescein-N-hydroxysuccinimide Ester; CFSE; Carboxyfluorescein N-succinimidyl ester; Carboxyfluorescein succinimidyl ester; 6-Carboxyfluorescein N-succinimidyl ester; 6-FAM, SE; 6-Carboxyfluorescein N-hydroxysuccinimide ester

Database IDs

• CAS Number: 92557-81-8
• MDL Number: MFCD00077323
• Beilstein Number: 8024096
• PubChem SID: 24892568; 162220754
• PubChem CID: 2762614
• Wikipedia Title: Carboxyfluorescein_succinimidyl_ester

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.1072505
• LogD (pH = 7.4): 3.087054
• Log P: 3.107511
• Molar Refractivity: 119.0301 cm^3
• Polarizability: 45.04112 Å^3
• Polar Surface Area: 139.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 492 nm; λem 517 nm (pH 8.0)

Safety Information

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

Product Information

• Shipped in: wet ice
• Mol. Weight: mol wt 473.39
• Empirical Formula (Hill Notation): C25H15NO9

DETAILS

Sigma Aldrich - C3984

Biochem/physiol Actions
An amine-reactive succinimidyl ester carboxyfluorescein which yields carboxyamides that are more resistant to hydrolysis than fluorescein conjugates prepared with FITC.

Toronto Research Chemicals - C178355

6-Carboxyfluorescein-N-hydroxysuccinimide Ester is a commonly used fluorescent reagent for the labelling of peptides, proteins and nucleotides.

REFERENCES

• Misra, A. et al.: Anal. Biochem., 369, 248 (2007)
• Breeuwer, P. et al.: Appl. Environ. Microbiol., 62, 178 (2007)