5-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 155951
• Molecular Formular: C25H15NO9
• Molecular Mass: 473.3879
• Monoisotopic Mass: 473.07468107
• SMILES: c1cc(c(cc1C(=O)ON1C(=O)CCC1=O)C(=O)O)c1c2ccc(cc2oc2cc(=O)ccc12)O
• Canonical SMILES: Oc1ccc2c(c1)oc1c(c2c2ccc(cc2C(=O)O)C(=O)ON2C(=O)CCC2=O)ccc(=O)c1
• InChI: InChI=1S/C25H15NO9/c27-13-2-5-16-19(10-13)34-20-11-14(28)3-6-17(20)23(16)15-4-1-12(9-18(15)24(31)32)25(33)35-26-21(29)7-8-22(26)30/h1-6,9-11,27H,7-8H2,(H,31,32)
• InChIKey: TWOKNYRPKCLMAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 5-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• Synonyms: 5-Carboxyfluorescein N-succinimidyl ester

Database IDs

• CAS Number: 92557-80-7
• MDL Number: MFCD00077322
• Beilstein Number: 7865828
• PubChem SID: 24889738; 162250089
• PubChem CID: 4564399

CALCULATED PROPERTIES

• Acid pKa: 3.5239582
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.099380195
• LogD (pH = 7.4): -2.1479456
• Log P: 1.8235531
• Molar Refractivity: 131.2226 cm^3
• Polarizability: 45.015423 Å^3
• Polar Surface Area: 147.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 492 nm; λem 520 nm in 0.1 M Tris 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

• Purity: ≥90% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C25H15NO9

DETAILS

Sigma Aldrich - 92846

Other Notes
Derivative of fluorescein giving stable derivative upon conjugation with biopolymers. Fluorescent probe for nucleotides1,2; Reagent for fluorescent derivatization in capillary electrophoresis3