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596-09-8

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596-09-8 Usage

Description

Fluorescein diacetate (FDA) is a cell-permeant esterase substrate that can serve as a viability probe that measures both enzymatic activity, which is require to activate its fluorescence, and cell-membrane integrity, which is required for intracellular retention of their fluorescent product. Upon hydrolysis by intracellular esterases, this AM ester yields fluorescein.

Chemical Properties

Light yellow powder

Uses

Fluorescein diacetate is a non-fluorescent molecule, which is hydrolysed to fluorescent fluorescein in live cells. Dead cells cannot accumulate or hydrolyse FDA. It has been used for the differentiation of live cells from dead cells. It can be also used as a fluorogenic substrate for hGSTP1-1.

Application

Diacetylfluorescein is used in fluorometric staining in the imaging of mammalian cells. Also used in the synthesis of nanocrystal biolabels with releasable fluorophores used in immunoassays. Dyes and metabolites.

Biotechnological Applications

Fluorescein Diacetate Stain is an esterase substrate that can permeate cell membranes. In viable cells with an active metabolism, intracellular esterases hydrolyze Fluorescein Diacetate Stain to produce the green fluorescent compound fluorescein. Fluorescein accumulates in viable cells, causing them to fluoresce green.Fluorescein Diacetate Stain can be used with Propidium Iodide Stain for Yeast to assess cell viability with the automated fluorescence cell counters of the LUNA? family. Viable cells convert fluorescein diacetate into fluorescein and thus fluoresce green. Nonviable cells take up propidium iodide and fluoresce red.Fluorescence Signal Enhancer 1 can be used with Fluorescein Diacetate Stain to inhibit ATP-dependent fluorescein efflux from metabolically active cells. This will result in lower background and increased signal intensity, thereby enhancing the fluorescein signal-to-noise ratio.

Check Digit Verification of cas no

The CAS Registry Mumber 596-09-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 6 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 596-09:
(5*5)+(4*9)+(3*6)+(2*0)+(1*9)=88
88 % 10 = 8
So 596-09-8 is a valid CAS Registry Number.
InChI:InChI=1/C24H16O7/c1-13(25)28-15-7-9-19-21(11-15)30-22-12-16(29-14(2)26)8-10-20(22)24(19)18-6-4-3-5-17(18)23(27)31-24/h3-12H,1-2H3

596-09-8 Well-known Company Product Price

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  • TCI America

  • (F0240)  Fluorescein Diacetate  >98.0%(HPLC)

  • 596-09-8

  • 5g

  • 385.00CNY

  • Detail
  • Alfa Aesar

  • (B24466)  Fluorescein diacetate, 97%   

  • 596-09-8

  • 5g

  • 467.0CNY

  • Detail
  • Alfa Aesar

  • (B24466)  Fluorescein diacetate, 97%   

  • 596-09-8

  • 25g

  • 1462.0CNY

  • Detail
  • Alfa Aesar

  • (B24466)  Fluorescein diacetate, 97%   

  • 596-09-8

  • 100g

  • 3647.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000454)  Diacetylfluorescein  European Pharmacopoeia (EP) Reference Standard

  • 596-09-8

  • Y0000454

  • 1,880.19CNY

  • Detail
  • USP

  • (1182000)  Diacetylfluorescein  United States Pharmacopeia (USP) Reference Standard

  • 596-09-8

  • 1182000-200MG

  • 4,662.45CNY

  • Detail

596-09-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Fluorescein Diacetate

1.2 Other means of identification

Product number -
Other names (6'-acetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:596-09-8 SDS

596-09-8Synthetic route

acetic acid
64-19-7

acetic acid

fluorescein
2321-07-5

fluorescein

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With phosphorus pentoxide at 60℃; for 2h; solid phase reaction;94%
acetic anhydride
108-24-7

acetic anhydride

fluorescein
2321-07-5

fluorescein

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2.5h;91%
for 3 - 5h; Heating / reflux;75%
Reflux;72.6%
acetyl chloride
75-36-5

acetyl chloride

fluorescein
2321-07-5

fluorescein

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With pyridine; acetic acid
With pyridine; dmap In dichloromethane for 1h;
fluorescein
2321-07-5

fluorescein

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With sodium acetate; acetic anhydride
With sulfuric acid; acetic anhydride
With Ketene; acetone
With acetic anhydride
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

5-bromofluorescein diacetate
620960-03-4

5-bromofluorescein diacetate

A

fluorescein diacetate
596-09-8

fluorescein diacetate

B

C30H27BO9
649734-78-1

C30H27BO9

Conditions
ConditionsYield
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); triethylamine In 1,4-dioxane at 80℃; for 20h;
5-bromofluorescein diacetate
620960-03-4

5-bromofluorescein diacetate

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; H-BO2C6H12; triethylamine In 1,4-dioxane at 80℃; for 20h;
phthalic anhydride
85-44-9

phthalic anhydride

activated aluminium

activated aluminium

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 195 - 200 °C
View Scheme
Multi-step reaction with 2 steps
1: concentrated sulfuric acid
2: pyridine; glacial acetic acid
View Scheme
2-(2,4-dihydroxybenzoyl)benzoic acid
2513-33-9

2-(2,4-dihydroxybenzoyl)benzoic acid

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: beim Erhitzen ueber den Schmelzpunkt
View Scheme
recorcinol
108-46-3

recorcinol

phenoldiazonium chloride-(4)

phenoldiazonium chloride-(4)

fluorescein diacetate
596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 195 - 200 °C
View Scheme
fluorescein diacetate
596-09-8

fluorescein diacetate

fluorescein
2321-07-5

fluorescein

Conditions
ConditionsYield
Stage #1: fluorescein diacetate With sodium hydroxide In methanol; water for 1.5h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water at 20 - 25℃; for 1h; pH=1 - 2.5;
80%
With water In acetonitrile pH=4.8; aq. acetate buffer;
With porcine liver carboxylesterase In 2-methoxy-ethanol; water at 37℃; for 0.5h; pH=8; Enzymatic reaction;
fluorescein diacetate
596-09-8

fluorescein diacetate

dihydrofluorescein diacetate
35340-49-9

dihydrofluorescein diacetate

Conditions
ConditionsYield
With acetic acid; zinc In tetrahydrofuran at 85℃; for 0.25h; Microwave irradiation;74%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 18h;
sulfuric acid
7664-93-9

sulfuric acid

fluorescein diacetate
596-09-8

fluorescein diacetate

4.5-dinitro-fluorescein diacetate

4.5-dinitro-fluorescein diacetate

Conditions
ConditionsYield
at 0℃; beim Nitrieren;
nitric acid
7697-37-2

nitric acid

fluorescein diacetate
596-09-8

fluorescein diacetate

tetranitrofluorescein hydrate

tetranitrofluorescein hydrate

fluorescein diacetate
596-09-8

fluorescein diacetate

fluorescein free acid
518-45-6

fluorescein free acid

Conditions
ConditionsYield
With Ac-His-Lys(Ac-His)-Leu-Lys[Ac-His-Lys(Ac-His)-Leu]-Val-Lys{Ac-His-Lys(Ac-His)-Leu-Lys[Ac-His-Lys(Ac-His)-Leu]-Val}-Lys-OH trifluoroacetate In acetonitrile at 34℃; pH=7.6; Kinetics; Reagent/catalyst; aq. phosphate buffer;
With seryl-histidine dipeptide; sodium hydroxide In aq. buffer at 50℃; for 48h; pH=6; Sealed tube;
fluorescein diacetate
596-09-8

fluorescein diacetate

C33H28O9

C33H28O9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 20 °C / 760.05 Torr
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
View Scheme
fluorescein diacetate
596-09-8

fluorescein diacetate

C29H24O7

C29H24O7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 20 °C / 760.05 Torr
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
3: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness
View Scheme
fluorescein diacetate
596-09-8

fluorescein diacetate

C35H32O7

C35H32O7

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 20 °C / 760.05 Torr
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
3: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness
4: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
View Scheme
fluorescein diacetate
596-09-8

fluorescein diacetate

3',6'-bis-allyloxy-spiro[phthalan-1,9'-xanthen]-3-one
855751-82-5

3',6'-bis-allyloxy-spiro[phthalan-1,9'-xanthen]-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 20 °C / 760.05 Torr
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
3: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness
4: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
View Scheme
fluorescein diacetate
596-09-8

fluorescein diacetate

fluorescein dianion
53677-98-8

fluorescein dianion

Conditions
ConditionsYield
With carboxyesterase; N,N-diethy-N-(4-(1,2,2-triphenylvinyl)benzyl)lhexadecan-1-aminium In dimethyl sulfoxide at 37℃; for 0.5h; pH=7.4; Enzymatic reaction;
fluorescein diacetate
596-09-8

fluorescein diacetate

C20H14O5

C20H14O5

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.333333h; Reflux;

596-09-8Relevant articles and documents

Endoplasmic Reticulum Targeting Reactive Oxygen Species Sensor Based on Dihydrofluorescein: Application of Endoplasmic Reticulum Stress

Le, Hoa Thi,Jo, Hye-Ryeong,Oh, Se-Yun,Jung, Jinwook,Kim, Young Gi,Kang, Chulhun,Kim, Tae Woo

supporting information, p. 279 - 285 (2020/12/21)

Endoplasmic reticulum (ER) has a unique redox environment, which plays critical roles in the organelle's function and in its pathological responses such as ER stress. In this work, we introduce an ER-targeting fluorogenic reactive oxygen species (ROS) chemosensor (ER-Flu) from copper(I)-catalyzed alkyne-azide cycloaddition of 3-propargyl ester of 2′,7′-dichlorodihydrofluorescein diacetate and N3-glibenclamide, which were adopted as a fluorogenic ROS sensing module and an ER-targeting module, respectively. Thereby, a series of confocal microscopic experiments of ER-Flu demonstrated that the sensor localizes in ER of the live cells and that ROS are elevated in the cells by ER stress inducers such as thapsigargin, brefeldin A, and tunicamycin.

5-hydroxymethylfurfural- and fluorescein-fused fluorescence probe of mast cells (RBL-2H3): Synthesis, photophysical properties, and bioimaging

Huang, Limin,Wei, Di,Wu, Zibo,Hou, Yajing,Xie, Yitong,Liu, Zhenru,Wang, Cheng,Che, Delu,Lei, Yibo,He, Huaizhen

, p. 1963 - 1971 (2018/09/06)

A fluorescent probe (Fluo-HMF) was developed via introduction of a furfural moiety into the fluorescein molecular skeleton, aiming at specially labeling cell membrane of mast cells. To illustrate its specificity, we designed and synthesized a series of fluorescent compounds based on fluorescein molecular skeleton. The fluorescent properties of Fluo-HMF were investigated, which were in accordance with theoretical calculations. Compared with other fluorescein derivatives, Fluo-HMF could specially label RBL-2H3 cells. The results suggested that Fluo-HMF could be used as a fluorescent probe for bioimaging on some related research of allergic mechanism.

A ratiometric fluorescent system for carboxylesterase detection with AIE dots as FRET donors

Wu, Yinglong,Huang, Shuailing,Zeng, Fang,Wang, Jun,Yu, Changmin,Huang, Jing,Xie, Huiting,Wu, Shuizhu

supporting information, p. 12791 - 12794 (2015/08/18)

A ratiometric fluorescent system for CaE detection with AIE dots as the FRET donors was designed. Upon enzymatic reaction, electrostatic interaction between the cationic TPE-N+ dots and the enzymatic reaction product - the negatively charged fluorescein molecules - allows the FRET process to proceed, thus affording the ratiometric fluorescence CaE assay.

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