Dichlorofluorescein

Dichlorofluorescein
Names

IUPAC name 2',7'-dichloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one
Identifiers
CAS Number	76-54-0^N
ChEBI	CHEBI:51596^Y
ChEMBL	ChEMBL1908059^N
ChemSpider	58471^Y
Jmol interactive 3D	Image
PubChem	64944
InChI InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H^Y Key: VFNKZQNIXUFLBC-UHFFFAOYSA-N^Y InChI=1/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H Key: VFNKZQNIXUFLBC-UHFFFAOYAO InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H Key: VFNKZQNIXUFLBC-UHFFFAOYSA-N
SMILES Clc5cc4c(Oc1cc(O)c(Cl)cc1C34OC(=O)c2c3cccc2)cc5O
Properties
Chemical formula	C₂₀H₁₀Cl₂O₅
Molar mass	401.20 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dichlorofluorescein (DCF) is an organic dye of the fluorescein family, being substituted at the 2 and 7 positions by chloride.

It is used as an indicator for argentometry by Fajans method.^[1]^[2]

It is also used in the cellular antioxidant activity (CAA) assay. Dichlorofluorescin is a probe that is trapped within cells and is easily oxidized to fluorescent dichlorofluorescein. The method measures the ability of compounds to prevent the formation of DCF by 2,2'-Azobis(2-amidinopropane) dihydrochloride (ABAP)-generated peroxyl radicals in human hepatocarcinoma HepG2 cells.^[3]

References

↑ Kolthoff, I. M.; Lauer, W. M.; Sunde, C. J. (1929). "The Use of Dichlorofluorescein as an Adsorption Indicator for the Argentometric Titration of Chlorides". Journal of the American Chemical Society 51 (11): 3273. doi:10.1021/ja01386a014.
↑ Bambach, Karl; Rider, T. H. (1935). "Volumetric Determinations of Halides: Use of Dichlorofluorescein as an Adsorption Indicator". Industrial & Engineering Chemistry Analytical Edition 7 (3): 165. doi:10.1021/ac50095a012.
↑ Wolfe, K. L.; Liu, R. H. (2007). "Cellular Antioxidant Activity (CAA) Assay for Assessing Antioxidants, Foods, and Dietary Supplements". Journal of Agricultural and Food Chemistry 55 (22): 8896–8907. doi:10.1021/jf0715166. PMID 17902627.

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