Fluorescein

Base Information

• Chemical Name: Fluorescein
• CAS No.: 2321-07-5
• Deprecated CAS: 126605-73-0,213880-86-5,518-46-7,770677-61-7,213880-86-5,518-46-7,770677-61-7
• Molecular Formula: C20H12O5
• Molecular Weight: 332.312
• Hs Code.: 32042000
• European Community (EC) Number: 219-031-8
• NSC Number: 759114,667256
• UNII: TPY09G7XIR
• DSSTox Substance ID: DTXSID0038887
• Nikkaji Number: J7.875A
• Wikipedia: Fluorescein
• Wikidata: Q410922
• NCI Thesaurus Code: C61766
• RXCUI: 25138
• ChEMBL ID: CHEMBL1057
• Mol file: 2321-07-5.mol

Synonyms:Fluorescein(8CI);3,6-Dihydroxyspiro[xanthene-9,3'-phthalide];3',6'-Fluorandiol;Benzoic acid,2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-;C.I. 45350:1;D and C Yellow No. 7;3',6'-Dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one;C Yellow No. 7;Japan Yellow 201;Japan Yellow No. 201;Resorcinolphthalein;Yellow fluorescein;

Chemical Property of Fluorescein

Chemical Property:

• Appearance/Colour: orange-red crystalline powder
• Melting Point: 314-316 °C
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 620.8 °C at 760 mmHg
• PKA: 2.2, 4.4, 6.7(at 25℃)
• Flash Point: 232.6 °C
• PSA: 87.74000
• Density: 1.602 g/cm³
• LogP: 3.96860
• Storage Temp.: −20°C
• Solubility.: Solubility Insoluble in water, ether, benzene, chloroform; solub
• Water Solubility.: insoluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 332.06847348
• Heavy Atom Count: 25
• Complexity: 522

Purity/Quality:

98%, ^*data from raw suppliers

Fluorescein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43-36-36/37/38
• Safety Statements: 22-24/25-37/39-26-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
• Recent ClinicalTrials: Advanced Gastrointestinal Endoscopic Imaging
• Recent EU Clinical Trials: Comparison of Fluorescein-INtra-VItal microscopy Versus conventional frozen section diagnosis for intraOperative histopathological evaluation
• Recent NIPH Clinical Trials: A pilot study of indocyanine green fluorescein imaging for detecting the serosal and mucosal blood flow of the reconstructed gastric conduit after esophagectomy
• Description: Fluorescein is a synthetic organic compound available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used as a fluorescent tracer for many applications. Fluorescein is a fluorophore commonly used in microscopy, in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains, and in dye tracing. Fluorescein has an absorption maximum at 494 nm and emission maximum of 521 nm (in water). The major derivatives are fluorescein isothiocyanate (FITC) and, in oligonucleotide synthesis, 6-FAM phosphoramidite. Fluorescein also has an isosbestic point (equal absorption for all pH values) at 460 nm. Fluorescein is also known as a color additive (D&C Yellow no. 7). The disodium salt form of fluorescein is known as uranine or D&C Yellow no. 8. The color of its aqueous solution varies from green to orange as a function of the way it is observed: by reflection or by transmission, as it can be noticed in bubble levels in which fluorescein is added as a colorant to the alcohol filling the tube to increase the visibility of the air bubble and the precision of the instrument. More concentrated solutions of fluorescein can even appear red.
• Physical properties: The fluorescence of this molecule is very intense; peak excitation occurs at 494 nm and peak emission at 521 nm. Fluorescein has a pKa of 6.4, and its ionization equilibrium leads to pH-dependent absorption and emission over the range of 5 to 9. Also, the fluorescence lifetimes of the protonated and deprotonated forms of fluorescein are approximately 3 and 4 ns, which allows for pH determination from non intensity based measurements. The lifetimes can be recovered using time-correlated single photon counting or phase-modulation fluorimetry.
• Uses: Fluorescein is used as a fluorescent tracer for many applications including in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains and in dye tracing. It is used to localise multiple muscular ventricular septal defects during open heart surgery and confirm the presence of any residual defects. It is applied to teeth to reveal plaque. A fluorescent tracer used for many applications. It is used in ophthalmology as a tool in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It can attach to certain biologically active molecules, thus allowing biologists to target the fluorophore to specific proteins or structures within cells corneal trama indicator

Technology Process of Fluorescein

There total 76 articles about Fluorescein 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: 97.0%

phthalic anhydride (85-44-9) + recorcinol (108-46-3) → fluorescein (2321-07-5,126605-73-0)

Guidance literature:

In phosphoric acid; for 0.00833333h; Microwave irradiation;

DOI:10.1135/cccc20021779

Reference yield: 80.0%

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

Guidance literature:

fluorescein diacetate; With sodium hydroxide; In methanol; water; for 1.5h; Heating / reflux;

With hydrogenchloride; In ethanol; water; at 20 - 25 ℃; for 1h; pH=1 - 2.5;

Reference yield: 78.3%

fluoresceinamine (3326-34-9) → fluorescein (2321-07-5,126605-73-0)

Guidance literature:

With oxygen; nitrogen(II) oxide; at 25 ℃; pH=7.4; Air; aq. HEPES buffer;

DOI:10.1021/ic300379u

upstream raw materials:

phthalic anhydride

2',4'-dihydroxy-4-acetophenone

3,4-pyridinecarboxylic acid

recorcinol

Downstream raw materials:

2-(6'-ethoxy-3'-oxo-3'H-xanthene-9'-yl)benzoic acid ethyl ester

methyl 2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoate

ethyl fluorescein

erythrosine B

Refernces

• 1、 Bharathkumar, Kuruba,Durairaj, Arulappan,Mohanapriya, Raman,Obadiah, Asir,Ramanathan, Subramanian,Santhoshkumar, Palanichamy,Vasanthkumar, Samuel. "Synthesis and evaluation of intrinsic bioactivity of fluorescein and phenolphthalein derivatives". . . Retrieved 2021/09/28.
• 2、 Lee, Youngjun,Devaraj, Neal K.. "Lipase mimetic cyclodextrins". . p. 1090 - 1094. Retrieved 2021/02/06.