2-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,4-dicarboxylic acid; 4-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,3-dicarboxylic acid

• ChemBase ID: 156034
• Molecular Formular: C42H20Cl4O14
• Molecular Mass: 890.4118
• Monoisotopic Mass: 887.96071604
• SMILES: c1cc(c(cc1C(=O)O)C(=O)O)c1c2cc(c(cc2oc2cc(=O)c(cc12)Cl)O)Cl.c1cc(c(cc1C(=O)O)c1c2cc(c(cc2oc2cc(=O)c(cc12)Cl)O)Cl)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(c(c1)c1c2cc(Cl)c(=O)cc2oc2c1cc(Cl)c(c2)O)C(=O)O.OC(=O)c1ccc(c(c1)C(=O)O)c1c2cc(Cl)c(=O)cc2oc2c1cc(Cl)c(c2)O
• InChI: InChI=1S/2C21H10Cl2O7/c22-13-4-11-17(6-15(13)24)30-18-7-16(25)14(23)5-12(18)19(11)10-3-8(20(26)27)1-2-9(10)21(28)29;22-13-4-11-17(6-15(13)24)30-18-7-16(25)14(23)5-12(18)19(11)9-2-1-8(20(26)27)3-10(9)21(28)29/h2*1-7,24H,(H,26,27)(H,28,29)
• InChIKey: WHFHRELKGQJJBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,4-dicarboxylic acid; 4-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,3-dicarboxylic acid
• IUPAC Traditional name: 2-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)benzene-1,4-dicarboxylic acid; 4-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)benzene-1,3-dicarboxylic acid
• Synonyms: 5(6)-Carboxy-2′,7′-dichlorofluorescein

Database IDs

• CAS Number: 111843-78-8
• MDL Number: MFCD00037452
• PubChem SID: 162250172; 24853090
• PubChem CID: 16211576

CALCULATED PROPERTIES

• Acid pKa: 3.303657
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.32901102
• LogD (pH = 7.4): -4.5499654
• Log P: 3.639062
• Molar Refractivity: 120.2649 cm^3
• Polarizability: 40.615814 Å^3
• Polar Surface Area: 121.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble (pH ≥ 5)
• Melting Point: ≥250 °C(lit.)
• pKa: 5.1
• Fluorescence: λex 504 nm; λem 529 nm in 0.1 M Tris pH 8.0

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (TLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C21H10Cl2O7

DETAILS

Sigma Aldrich - 21882

Application
suitable as pH-indicator
Other Notes
Fluorescent intracellular pH indicator in the pH 4-5 range1