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4091-99-0

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4091-99-0 Usage

Description

DCFH (commonly known as dichlorofluorescin) is used as an indicator of peroxynitrite formation. DCFH is supplied as the diacetate ester. Following enzymatic or base-catalyzed cleavage of the diacetate groups, it is readily oxidized to the highly fluorescent product dichlorofluorescein (DHF). Peroxynitrite is an efficient mediator of this oxidation and neither NO, superoxide, nor hydrogen peroxide alone appear to oxidize DCFH. Formation of DHF can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 502 and 523 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 59,500 M?1cm?1).

Chemical Properties

white to yellow-beige or pale pink powder

Uses

Different sources of media describe the Uses of 4091-99-0 differently. You can refer to the following data:
1. Cell-permeable fluorogenic probe used to measure reactive oxygen species (ROS) within cells by detection of enzymatically formed hydrogen peroxide.
2. 2',7'-Dichlorodihydrofluorescein as a cell-permeable non-fluorescent probe. It is de-esterified intracellularly and turns to highly fluorescent 2’7’dichlorofluorescein upon oxidation.
3. 2′,7′-Dichlorofluorescin diacetate is a cell-permeable non-fluorescent probe. 2′,7′-Dichlorofluorescin diacetate is de-esterified intracellularly and turns to highly fluorescent 2′,7′-dichlorofluorescein upon oxidation.Applications include sensitive and rapid quantitation of oxygen-reactive species in response to oxidative metabolism; microplate assay for detecting oxidative products in phagocytic cells, and quantitative multiwell myeloid differentiation assay.

General Description

Cell-permeable fluorogenic probe that is useful for the detection of reactive oxygen species (ROS) and nitric oxide (?NO) and for the determination of the degree of overall oxidative stress.

Biochem/physiol Actions

Cell permeable: yes

Check Digit Verification of cas no

The CAS Registry Mumber 4091-99-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,9 and 1 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4091-99:
(6*4)+(5*0)+(4*9)+(3*1)+(2*9)+(1*9)=90
90 % 10 = 0
So 4091-99-0 is a valid CAS Registry Number.

4091-99-0 Well-known Company Product Price

  • Brand
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  • Sigma

  • (D6883)  2′,7′-Dichlorofluorescin diacetate  ≥97%

  • 4091-99-0

  • D6883-50MG

  • 472.68CNY

  • Detail
  • Sigma

  • (D6883)  2′,7′-Dichlorofluorescin diacetate  ≥97%

  • 4091-99-0

  • D6883-250MG

  • 1,668.42CNY

  • Detail

4091-99-0Synthetic route

2',7'-dichlorodihydrofluorescein diacetate
2044-85-1

2',7'-dichlorodihydrofluorescein diacetate

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 18h;
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

propargyl alcohol
107-19-7

propargyl alcohol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;61%
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

2,7-dichlorofluorescein

2,7-dichlorofluorescein

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase In water
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol / 0.5 h / 20 °C
2: 3-(N-morpholino)propanesulfonic acid; cysteamine; air / CuSO4; 1,10-phenanthroline / 25 °C / pH 7
View Scheme
With Ac-IHIHIQI-CONH2; water; copper(II) ion pH=8; Kinetics; Reagent/catalyst;
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol
2: C35H29CuN3O4 / ethanol; aq. phosphate buffer / pH 7.4
View Scheme
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid
106070-31-9

2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 0.5h;
With sodium hydroxide for 0.5h; cooling;
With sodium hydroxide In ethanol at 20℃; for 0.5h; Darkness;
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

2',7'-dichlorofluorescein
76-54-0

2',7'-dichlorofluorescein

Conditions
ConditionsYield
With hemin; d(ATTGTGCGTCATCCCTTACGTCAGTGGAG), screened from Cauliflower mosaic virus (CaMV) 35S promoter; d(CTCCACTGACGTAATGGGTAGGG); d(GGGTTGGGCGGATGACGCACAAT); potassium chloride; ammonium acetate In water at 20℃; for 0.166667h; pH=7; aq. buffer;
With water; oxygen Irradiation;
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C29H22Cl2O7

C29H22Cl2O7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere; Darkness
View Scheme
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C35H30Cl2O7

C35H30Cl2O7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere; Darkness
3: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
View Scheme
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C26H18Cl2O5

C26H18Cl2O5

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere; Darkness
3: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
View Scheme
2,4-dimethoxylbenzyl alcohol
7314-44-5

2,4-dimethoxylbenzyl alcohol

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C33H26Cl2O9

C33H26Cl2O9

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere;149.4 mg
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C50H45Cl3N6O12S

C50H45Cl3N6O12S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 1 h / 20 °C
2: copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; sodium L-ascorbate / tetrahydrofuran; water; ethanol / 2 h / 20 °C
View Scheme
2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid
4091-99-0

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid

C46H41Cl3N6O10S

C46H41Cl3N6O10S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 1 h / 20 °C
2: copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; sodium L-ascorbate / tetrahydrofuran; water; ethanol / 2 h / 20 °C
3: sodium hydroxide / methanol / 0.5 h / 37 °C
View Scheme

4091-99-0Relevant articles and documents

Synthesis of high contrast fluorescein-diethers for rapid bench-top sensing of palladium

Kitley, Weston R.,Santa Maria, Peter J.,Cloyd, Ryan A.,Wysocki, Laura M.

, p. 8520 - 8523 (2015)

A new series of palladium sensors based on fluorescein bis(allyl ether) compounds has been designed. We utilized reduced fluoresceins as key synthetic intermediates. These probes exhibit negligible background fluorescence and rapid reaction with palladium, allowing a concentration of 100 ppt to be detected in minutes using a handheld UV lamp. This journal is

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