3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid; 3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid

• ChemBase ID: 156035
• Molecular Formular: C50H28Cl4O18
• Molecular Mass: 1058.55852
• Monoisotopic Mass: 1056.00297478
• SMILES: CC(=O)Oc1cc2c(cc1Cl)C1(c3ccc(cc3C(=O)O1)C(=O)O)c1cc(c(cc1O2)OC(=O)C)Cl.CC(=O)Oc1cc2c(cc1Cl)C1(c3cc(ccc3C(=O)O1)C(=O)O)c1cc(c(cc1O2)OC(=O)C)Cl
• Canonical SMILES: CC(=O)Oc1cc2Oc3cc(OC(=O)C)c(cc3C3(c2cc1Cl)OC(=O)c1c3cc(cc1)C(=O)O)Cl.CC(=O)Oc1cc2Oc3cc(OC(=O)C)c(cc3C3(c2cc1Cl)OC(=O)c1c3ccc(c1)C(=O)O)Cl
• InChI: InChI=1S/2C25H14Cl2O9/c1-10(28)33-21-8-19-15(6-17(21)26)25(14-4-3-12(23(30)31)5-13(14)24(32)36-25)16-7-18(27)22(34-11(2)29)9-20(16)35-19;1-10(28)33-21-8-19-15(6-17(21)26)25(14-5-12(23(30)31)3-4-13(14)24(32)36-25)16-7-18(27)22(34-11(2)29)9-20(16)35-19/h2*3-9H,1-2H3,(H,30,31)
• InChIKey: LZMPJBOMBCYYMP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid; 3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid
• IUPAC Traditional name: 3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid; 3',6'-bis(acetyloxy)-2',7'-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid
• Synonyms: 5(6)-Carboxy-2′,7′-dichlorofluorescein diacetate

Database IDs

• CAS Number: 127770-45-0
• MDL Number: MFCD08459585
• Beilstein Number: 7505106
• PubChem SID: 162250173; 24853092
• PubChem CID: 16211578

CALCULATED PROPERTIES

• Acid pKa: 3.832692
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.8970404
• LogD (pH = 7.4): 1.3206042
• Log P: 4.5676675
• Molar Refractivity: 126.3889 cm^3
• Polarizability: 48.389904 Å^3
• Polar Surface Area: 125.43 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; methanol: soluble
• Melting Point: 210 °C (dec.)(lit.)
• Fluorescence: λex 470 nm; λem 529 nm in 0.1 M Tris pH 8.0 (esterase)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• 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: -20°C

Product Information

• Purity: ≥85% (HPCE)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C25H14Cl2O9

DETAILS

Sigma Aldrich - 21884

Analysis Note
Excmax: 504 nm (Lit.)
Other Notes
Intracellular esterase substrate with low sensitivity of fluorescence to intracellar pH1