Fluorescein diacetate

Base Information

• Chemical Name: Fluorescein diacetate
• CAS No.: 596-09-8
• Molecular Formula: C24H16O7
• Molecular Weight: 416.387
• Hs Code.: 32129000
• European Community (EC) Number: 209-877-6
• NSC Number: 667259,4726
• UNII: YL39R93PRE
• DSSTox Substance ID: DTXSID4060490
• Nikkaji Number: J4.484I
• Wikidata: Q27294565
• ChEMBL ID: CHEMBL1492044
• Mol file: 596-09-8.mol

Synonyms:3',6'-diacetylfluorescein;diacetylfluorescein;fluorescein 3',6'-diacetate;fluorescein diacetate;MFCD-5062;NSC-4726;NSC-667259;spiro(isobenzofuran-1(3h),9'-(9h)xanthen)-3-one, 3',6'-bis(acetyloxy)-

Chemical Property of Fluorescein diacetate

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 1.42E-14mmHg at 25°C
• Melting Point: 200-203 °C(lit.)
• Refractive Index: 1.681
• Boiling Point: 604.7 °C at 760 mmHg
• PKA: 6.4(at 25℃)
• Flash Point: 264 °C
• PSA: 88.13000
• Density: 1.47 g/cm³
• LogP: 4.10520
• Storage Temp.: −20°C
• Solubility.: acetone: soluble25mg/mL
• Water Solubility.: Soluble in chloroform, DMSO, ethanol, and water.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 416.08960285
• Heavy Atom Count: 31
• Complexity: 708

Purity/Quality:

99.9% ^*data from raw suppliers

Diacetylfluorescein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)OC(=O)C)C5=CC=CC=C5C(=O)O3
• 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.
• 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.

Technology Process of Fluorescein diacetate

There total 9 articles about Fluorescein diacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

acetic acid (64-19-7,77671-22-8) + fluorescein (2321-07-5,126605-73-0) → fluorescein diacetate (596-09-8)

Guidance literature:

With phosphorus pentoxide; at 60 ℃; for 2h; solid phase reaction;

DOI:10.1016/j.dyepig.2010.09.013

Reference yield: 91.0%

acetic anhydride (108-24-7) + fluorescein (2321-07-5,126605-73-0) → fluorescein diacetate (596-09-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1111/cbdd.13367

Reference yield:

fluorescein (2321-07-5,126605-73-0) → fluorescein diacetate (596-09-8)

Guidance literature:

With sodium acetate; acetic anhydride;

upstream raw materials:

acetic anhydride

fluorescein

acetyl chloride

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

Downstream raw materials:

dihydrofluorescein

fluorescein dianion

fluorescein free acid

fluorescein

Refernces

• 1、 Le, Hoa Thi,Nguyen, Dinh Phi Long,Shin, Hyo Seob,Jung, Woong,Kang, Chulhun,Kim, Tae Woo. "Chemistry of the carboxylic acid of dihydrofluorescein in oxidation and its application to fluorogenic ROS sensing". . p. 461 - 468. Retrieved 2021/07/19.
• 2、 Chyan, Wen,Kilgore, Henry R.,Gold, Brian,Raines, Ronald T.. "Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging". . p. 4297 - 4304. Retrieved 2017/04/28.