2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,3-dicarboxylic acid; 2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzene-1,4-dicarboxylic acid

• ChemBase ID: 156322
• Molecular Formular: C42H16Br8O14
• Molecular Mass: 1383.80004
• Monoisotopic Mass: 1375.40070119
• SMILES: c1cc(c(c(c1)C(=O)O)c1c2cc(c(c(c2oc2c(c(=O)c(cc12)Br)Br)Br)O)Br)C(=O)O.c1cc(c(cc1C(=O)O)c1c2cc(c(c(c2oc2c(c(=O)c(cc12)Br)Br)Br)O)Br)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(c(c1)c1c2cc(Br)c(c(c2oc2c1cc(Br)c(=O)c2Br)Br)O)C(=O)O.Brc1cc2c(c(c1=O)Br)oc1c(c2c2c(cccc2C(=O)O)C(=O)O)cc(c(c1Br)O)Br
• InChI: InChI=1S/2C21H8Br4O7/c22-11-4-9-13(8-3-6(20(28)29)1-2-7(8)21(30)31)10-5-12(23)17(27)15(25)19(10)32-18(9)14(24)16(11)26;22-10-4-8-13(12-6(20(28)29)2-1-3-7(12)21(30)31)9-5-11(23)17(27)15(25)19(9)32-18(8)14(24)16(10)26/h2*1-5,26H,(H,28,29)(H,30,31)
• InChIKey: BEFSXKPEQVWGHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 132201-84-4
• MDL Number: MFCD00467490
• PubChem SID: 162250460
• PubChem CID: 44119976

CALCULATED PROPERTIES

• Acid pKa: 3.064059
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.3667298
• LogD (pH = 7.4): -2.8730516
• Log P: 5.5185995
• Molar Refractivity: 141.133 cm^3
• Polarizability: 48.7698 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 ≥ 6)
• Melting Point: ≥220 °C(lit.)
• pKa: 3.6
• Fluorescence: λex 519 nm; λem 542 nm in 0.1 M Tris pH 9.0

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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPCE)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C21H8Br4O7

DETAILS

Sigma Aldrich - 21883

Application
suitable as pH-indicator
Other Notes
Fluorescent pH indicator for the acidic range, and fluorescent label for amine modification and protein conjugation1