2-[2,7-bis(2-carboxyethyl)-6-hydroxy-3-oxo-3H-xanthen-9-yl]benzene-1,4-dicarboxylic acid

• ChemBase ID: 155091
• Molecular Formular: C27H20O11
• Molecular Mass: 520.4411
• Monoisotopic Mass: 520.10056146
• SMILES: c1cc(c(cc1C(=O)O)c1c2cc(c(cc2oc2cc(=O)c(cc12)CCC(=O)O)O)CCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CCc1cc2c(cc1O)oc1c(c2c2cc(ccc2C(=O)O)C(=O)O)cc(c(=O)c1)CCC(=O)O
• InChI: InChI=1S/C27H20O11/c28-19-10-21-17(7-12(19)2-5-23(30)31)25(16-9-14(26(34)35)1-4-15(16)27(36)37)18-8-13(3-6-24(32)33)20(29)11-22(18)38-21/h1,4,7-11,28H,2-3,5-6H2,(H,30,31)(H,32,33)(H,34,35)(H,36,37)
• InChIKey: DKROGDOAOXDINY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2,7-bis(2-carboxyethyl)-6-hydroxy-3-oxo-3H-xanthen-9-yl]benzene-1,4-dicarboxylic acid
• IUPAC Traditional name: 2-[2,7-bis(2-carboxyethyl)-3-hydroxy-6-oxoxanthen-9-yl]benzene-1,4-dicarboxylic acid
• Synonyms: BCECF; 2′,7′-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein

Database IDs

• CAS Number: 85138-49-4
• MDL Number: MFCD00036970
• Beilstein Number: 8375770
• PubChem SID: 162249229; 24892612; 24848736
• PubChem CID: 4241719

CALCULATED PROPERTIES

• Acid pKa: 2.5019383
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -4.7916756
• LogD (pH = 7.4): -11.4202385
• Log P: 1.9364246
• Molar Refractivity: 141.8019 cm^3
• Polarizability: 48.980747 Å^3
• Polar Surface Area: 195.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 482 nm; λem 520 nm in 0.1 M Tris pH 7.0

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)
• Grade: for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C27H20O11

DETAILS

Sigma Aldrich - C3411

Biochem/physiol Actions
Fluorescent indicator for measurement of cytoplasmic pH in lymphocytes.

Sigma Aldrich - 14560

Other Notes
Fluorescent indicator for the measurement of cytoplasmic pH in lymphocytes1; Reliable measure of in vitro cellular cytotoxicity2