Dichlorofluorescein: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460782986

| PIN = 2′,7′-Dichloro-3′,6′-dihydroxy-3''H''-spiro[<nowiki/>[2]benzofuran-1,9′-xanthen]-3-one

|Section1={{Chembox Identifiers

| 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

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 76-54-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 56NQM5UZT1

| PubChem = 64944

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 58471

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 51596

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1908059

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

}}

|Section2={{Chembox Properties

| C=20| H=10| Cl=2| O=5

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

'''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#Fajans method|argentometry by Fajans method]].<ref>{{cite journal | last1 = Kolthoff | first1 = I. M. | last2 = Lauer | first2 = W. M. | last3 = Sunde | first3 = C. J. | journal = Journal of the American Chemical Society | volume = 51 | pages = 3273 | year = 1929 | doi = 10.1021/ja01386a014 | title =The Use of Dichlorofluorescein as an Adsorption Indicator for the Argentometric Titration of Chlorides | issue = 11}}</ref><ref>{{cite journal | last1 =Bambach | first1 =Karl | last2 =Rider | first2 =T. H. | title =Volumetric Determinations of Halides: Use of Dichlorofluorescein as an Adsorption Indicator | journal =Industrial & Engineering Chemistry Analytical Edition | volume =7 | pages =165 | year =1935 | doi =10.1021/ac50095a012 | issue =3}}</ref>

When used as an indicator, upon reaching the equivalence point of a titration reaction the color shifts from colorless towards a faint pink.

It is also used in the [[cellular antioxidant activity]] (CAA) assay. Dichlorofluorescin (DCFH) is a probe that is trapped within cells and is easily oxidized to fluorescent dichlorofluorescein (DCF). 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.<ref>{{Cite journal | last1 = Wolfe | first1 = K. L. | last2 = Liu | first2 = R. H. | doi = 10.1021/jf0715166 | title = Cellular Antioxidant Activity (CAA) Assay for Assessing Antioxidants, Foods, and Dietary Supplements | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 22 | pages = 8896–8907 | year = 2007 | pmid = 17902627}}</ref> By itself, dichlorofluorescin (DCFH) also quantifies intracellular hydrogen peroxide as well as cellular [[oxidative stress]].<ref>{{Cite journal | last1 = LeBel | first1 = C. P. | last2 = Ischiropoulos | first2 = Harry | last3 = Bondy | first3 = S. C. | doi = 10.1021/tx00026a012 | title = Evaluation of the probe 2',7'-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress | journal = Chem. Res. Toxicol. | volume = 5 | issue = 2 | pages = 227–231 | year = 1992 | pmid = 1322737 | url = https://escholarship.org/content/qt19r571vt/qt19r571vt.pdf?t=nsppk9 }}</ref>

== References ==

{{Reflist}}

[[Category:Fluorone dyes]]

[[Category:Chloroarenes]]

[[Category:Spiro compounds]]

[[Category:Hydroxyarenes]]

[[Category:Triarylmethane dyes]]