35340-49-9

Basic information

• Product Name: DIHYDROFLUORESCEIN DIACETATE
• Synonyms: Diacetyldihydrofluorescein [for detection of alcohols and amines];dihydrofluorescein diacetate 90-95%;Diacetyldihydrofluorescein [for Detection of Alcohol and Amines];2-(3,6-Diacetoxy-9H-xanthen-9-yl)benzenecarboxylic acid;2-(3,6-Diacetoxy-9H-xanthen-9-yl)benzoic acid;Dihydroflourescein Diacetate;2-[3,6-Diacetoxy-9H-xanth-9-yl]benzoic acid;[for Detection of Alcohol and Amines]
• CAS NO: 35340-49-9
• Molecular Formula: C₂₄H₁₈O₇
• Molecular Weight: 418.4
• Mol File: 35340-49-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 213-215 °C(lit.)
• Boiling Point: 554.3 °C at 760 mmHg
• Flash Point: 190.3 °C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 4.01E-13mmHg at 25°C
• Refractive Index: 1.626
• PKA: 3.85±0.36(Predicted)
• BRN: 364167
• CAS DataBase Reference: DIHYDROFLUORESCEIN DIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROFLUORESCEIN DIACETATE(35340-49-9)
• EPA Substance Registry System: DIHYDROFLUORESCEIN DIACETATE(35340-49-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 35340-49-9(Hazardous Substances Data)

Usage

Uses

Dihydrofluorescein diacetate is a chemical used for intracellular staining. Dihydrofluorescein diacetate might be reactive toward a broad range of oxidizing reactions that may be increased during intracellular oxidant stress. Cell-loading studies indicate that dihydrofluorescein achieves higher intracellular concentrations than the other redox sensors such as 2'',7''-dichlorodihydrofluorescein and Dihydrorhodamine 123. Dihydrofluorescein diacetate is first hydrolyzed by cellular esterases to dihydrofluorescein and is then oxidized to fluorescein primarily by hydrogen peroxide.

InChI:InChI=1/C24H18O7/c1-13(25)29-15-7-9-19-21(11-15)31-22-12-16(30-14(2)26)8-10-20(22)23(19)17-5-3-4-6-18(17)24(27)28/h3-12,23H,1-2H3,(H,27,28)

Upstream product

• 518-44-5 dihydrofluorescein 
• 108-24-7 acetic anhydride 
• 2321-07-5 fluorescein 
• 97744-44-0 O,O'-Dibenzylfluorescein 

Downstream Products

• 548-25-4 erythrosine B 
• 518-44-5 dihydrofluorescein 

Relevant articles and documents

Reaction of Alcohols and Amines with Diacetyldihydrofluorescein (DADF): Conversion into Erythrosine-Derivatives on TLC-Plates by Ammonia and Iodine Vapors

Reaction of deacetylcolchicine (2) and colchifoline (3) with diacetyldihydrofluorescein (1, DADF) afforded the corresponding amide and ester derivatives, converted on TLC-plates after exposure to ammonia and iodine vapors into red colored pigments.This re

Chemistry of the carboxylic acid of dihydrofluorescein in oxidation and its application to fluorogenic ROS sensing

The conjugation site of dihydrofluorescein (H2F) is important for the rational design of H2F-based reactive oxygen species (ROS) sensors. Despite the prevalence of H2F analogs detecting cellular ROS, the role of the carboxylic acid of H2F in oxidation is still unclear. To get insight into the conjugation site of H2F, we synthesized H2F diacetate (2) and its amide derivative (3). The absorption and emission spectra of deacetylated 2 and 3 in the presence of H2O2/hematin showed that the carboxylic acid of H2F plays a crucial role in the oxidation of H2F. NMR and HPLC analysis of the oxidation product of deacetylated 3 showed a quantitative and fast generation of non-fluorescent spirolactam (F-Lactam). As regards these observations, we untouched the carboxylic acid at the 3rd position and designed an H2F-based ROS sensor (7) that conjugated the lipophilic chain at the 5th position instead. A series of confocal microscopic experiments of 7 demonstrated that 7 prefers the ER location and that ROS are elevated in the cells by ER stress inducers.