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D6665

Sigma-Aldrich

2′,7′-Dichlorofluorescein

~90% purity (TLC) (85- 100% purity), powder

Synonym(s):

Dichlorofluorescein; Fluorescein 27

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About This Item

Empirical Formula (Hill Notation):
C20H10Cl2O5
CAS Number:
76-54-0
Molecular Weight:
401.20
Beilstein:
58009
EC Number:
200-968-6
MDL number:
MFCD00005047
UNSPSC Code:
12171500
PubChem Substance ID:
24894041
NACRES:
NA.47
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Product Name

2′,7′-Dichlorofluorescein, suitable for use as an indicator in chloride titration, ~90% (TLC), powder

Quality Level

200

Assay

~90% (TLC)

form

powder

technique(s)

titration: suitable

mp

280 °C (dec.) (lit.)

solubility

ethanol: 25 mg/mL

density

0.79 g/cm3

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Oc1cc2Oc3cc(O)c(Cl)cc3C4(OC(=O)c5ccccc45)c2cc1Cl

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

InChI key

VFNKZQNIXUFLBC-UHFFFAOYSA-N

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General description

2′,7′-Dichlorofluorescein is an oxidation-sensitive fluorescent probe. 2′7′-dichlorofluorescein diacetate is oxidized to 2′7′-dichlorofluorescein in the presence of ROS (reactive oxygen species).citation

Application

2′,7′-Dichlorofluorescein has been used as an oxidation-sensitive fluorescent probe to measure ROS (reactive oxygen species) formation in cells.[1][2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5883
BCCL6807
BCCJ9431
BCCG9996
BCCF6570

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Cysteamine suppresses human peripheral blood mononuclear cells--human corneal endothelial cell reaction via reactive oxygen species reduction.
Shin YJ, et al.
Molecular Vision, 17, 3371-3378 (2011)
Vittoria Buccigrossi et al.
PloS one, 9(6), e99830-e99830 (2014-06-12)
Rotavirus (RV) infection causes watery diarrhea via multiple mechanisms, primarily chloride secretion in intestinal epithelial cell. The chloride secretion largely depends on non-structural protein 4 (NSP4) enterotoxic activity in human enterocytes through mechanisms that have not been defined. Redox imbalance
Janaína Kolling et al.
Cardiovascular toxicology, 11(1), 67-73 (2010-11-16)
Hyperhomocysteinemia is a risk factor for cardiovascular disease, stroke, and thrombosis; however, the mechanisms by which homocysteine triggers these dysfunctions are not fully understood. In the present study, we investigated the effect of chronic hyperhomocysteinemia on some parameters of oxidative
Aleksey Rukavishnikov et al.
Analytical biochemistry, 419(1), 9-16 (2011-08-27)
Cephalosporin was used to synthesize soluble and precipitating fluorogenic β-lactam substrates that demonstrated differential catalytic hydrolysis by three different subtypes of β-lactamase: TEM-1 (class A), p99 (class C), and a Bacillus cereus enzyme sold by Genzyme (class B). The most
Olga N Pakhomova et al.
Archives of biochemistry and biophysics, 527(1), 55-64 (2012-08-23)
Nanosecond pulsed electric field (nsPEF) is a novel modality for permeabilization of membranous structures and intracellular delivery of xenobiotics. We hypothesized that oxidative effects of nsPEF could be a separate primary mechanism responsible for bioeffects. ROS production in cultured cells
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Questions

1–4 of 4 Questions  

  1. What excitation /emission wavelengths are best for fluorescence detection of 2´,7´-Dichlorofluorescein?

    1 answer

    1. 2´,7´-Dichlorofluorescein can be detected at an excitation wavelength at 504 nm and emission wavelength at 529 nm in 0.1 M Tris pH 8.0.

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  2. What can be used to make a solution of 2´,7´-dichlorofluorescein?

    1 answer

    1. 2´,7´-Dichlorofluorescein is soluble at 25 mg/mL absolute ethanol with heating. 2´,7´-Dichlorofluorescein is also soluble in water at 0.1 mg/mL.

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  3. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  4. In what types of applications can 2´,7´-Dichlorofluorescein be used?

    1 answer

    1. Some applications for use of 2´,7´-Dichlorofluorescein are listed below. This product can be used for the determination of carbohydrates by fluorescence densitometry after TLC.  See G. Gübitz et al., J. Chromatogr., 117, 337, (1976). 2´,7´-Dichlorofluorescein as also been used in the determination of H2O2 by chemiluminescence. See the following references by H. Watanabe et al. Anal. Sci. 2, 461, (1986) and T. Segawa et al. Anal. Sci. 6, 763, (1990). This product has also been used as a  fluorescent additive used in indirect fluorimetric detection in OTC-HPLC. See W.D. Pfeffer and E.S. Yeung, J. Chromatogr., 506, 401, (1990).

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