Fluorescein-5-isothiocyanate

Base Information

• Chemical Name: Fluorescein-5-isothiocyanate
• CAS No.: 3326-32-7
• Deprecated CAS: 113394-21-1,122655-66-7,55177-69-0,86151-70-4,135680-00-1,1691330-05-8,1839547-28-2,2570982-74-8,1173-43-9,122655-66-7,135680-00-1,1691330-05-8,1839547-28-2,55177-69-0,86151-70-4
• Molecular Formula: C₂₁H₁₁NO₅S
• Molecular Weight: 389.388
• Hs Code.: 29329990
• European Community (EC) Number: 222-042-0
• UNII: I223NX31W9
• DSSTox Substance ID: DTXSID80892440
• Nikkaji Number: J205.408F
• Wikidata: Q59647575
• ChEMBL ID: CHEMBL516313
• Mol file: 3326-32-7.mol

Synonyms:5 Isothiocyanatofluorescein;5-Isothiocyanatofluorescein;FITC;Fluorescein (5 or 6)-Isothiocyanate;Fluorescein 5 isothiocyanate;Fluorescein 5 isothiocyanate Hydrochloride;Fluorescein-5-isothiocyanate;Fluorescein-5-isothiocyanate Hydrochloride;Hydrochloride, Fluorescein-5-isothiocyanate

Chemical Property of Fluorescein-5-isothiocyanate

Chemical Property:

• Appearance/Colour: Orange-yellow cryst.
• Vapor Pressure: 1.02E-22mmHg at 25°C
• Melting Point: >360 °C(lit.)
• Refractive Index: 1.715
• Boiling Point: 708.6oC at 760 mmHg
• PKA: 2.2, 4.4, 6.7(at 25℃)
• Flash Point: 382.4oC
• PSA: 120.44000
• Density: 1.54g/cm3
• LogP: 4.40010
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Slightly soluble in DMSO, ethanol, methanol DMF and acetone
• Water Solubility.: practically insoluble
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 389.03579362
• Heavy Atom Count: 28
• Complexity: 668

Purity/Quality:

99% ^*data from raw suppliers

FITC ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38-22
• Safety Statements: 22-45-36/37/39-26-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Indicator Dyes
• Canonical SMILES: C1=CC2=C(C=C1N=C=S)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
• Description: Fluorescein 5-isothiocyanate (5-FITC) is an isomer of fluorescein isothiocyanate (FITC), which is commonly used as a mixture of the 5- and 6-isothiocyanate isomers. It reacts with amine and thiol groups to form conjugates with proteins, lipids, and other molecules for detection by a variety of fluorescent-based applications. 5-FITC displays excitation/emission maxima of 494/519 nm, respectively.
• Uses: Fluorescein -5-isothiocyanate is a kind of fluorescent marker for biochemical applications. Reacts under mild conditions with primary amines and it is also used in modification of actin at lys-61, labelling of FAB and the modification of thiol groups. Fluorescein isothiocyanate isomer I has been used for the staining of conidia. Fluorescein isothiocyanate is used as fluorescent labeling reagent for proteins and for rapid identification of pathogens in fluorescent antibody technique. It is also used as a reagent for microsequencing of proteins and peptides (HPLC). On celite it is used for the labeling of fibrinogen. Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens

Technology Process of Fluorescein-5-isothiocyanate

There total 11 articles about Fluorescein-5-isothiocyanate 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: 83.59%

carbon disulfide (75-15-0,12122-00-8) + fluoresceinamine (3326-34-9) → fluorescein isothiocyanate (3326-32-7,27072-45-3)

Guidance literature:

carbon disulfide; fluoresceinamine; With triethylamine; In methanol; at 5 - 20 ℃; for 8h;

With copper(l) chloride; In methanol; for 2h; Temperature;

Reference yield:

C21H13NO5S2*C6H15N → fluorescein isothiocyanate (3326-32-7,27072-45-3)

Guidance literature:

With benzenesulfonyl chloride; In tetrahydrofuran; at 30 ℃; Large scale;

Reference yield:

fluorescein (2321-07-5,126605-73-0) → fluorescein isothiocyanate (3326-32-7,27072-45-3)

Guidance literature:

With ammonia; In water;

upstream raw materials:

fluorescein

3',6'-dihydroxy-5-nitrospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one

4-nitrophthalic acid

recorcinol

Downstream raw materials:

1-(2-aminoethyl)-3-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-yl)thiourea

8-{carboxy-[2-(fluoresceinylthioureido)ethyl]amido}octyl α-D-mannopyranoside

Refernces

An In-tether Chiral Center Modulates the Helicity, Cell Permeability, and Target Binding Affinity of a Peptide

10.1002/anie.201602806

The research focuses on the impact of an in-tether chiral center on the helicity, cell permeability, and target binding affinity of constrained peptides. The experiments involved the synthesis of peptide diastereomers with a carbon atom chiral center within the tether, which led to significant differences in helicity as confirmed by circular dichroism (CD) and NMR spectroscopy. Single crystal X-ray diffraction analysis was utilized to determine the absolute configuration of the chiral center in the helical form, which was found to be R. The study also investigated the influence of the chiral center on protease resistance and cell permeability, finding that the chiral center significantly improved these properties. Fluorescein Isothiocyanate (FITC) was used for labeling peptides to study cell permeability, creating FITC-bA-[cyclo-CRARS5(2-Ph)]-NH2 and FITC-bA-[cyclo-CRRRS5(2-Ph)]-NH2 (where bA is beta alanine and 2-Ph is a phenyl group). The researchers further explored the effect of peptide helicity and substitution groups at the tether chiral center on target binding affinity using model targets estrogen receptor alpha (ERa) and mammal double minute 2 (MDM2). The analyses included fluorescence polarization assays to measure binding affinities and in vitro serum stability assays to assess peptide degradation. The results demonstrated that the chiral center could modulate peptide properties, providing a method to study the relationship between peptide conformation and its biochemical/biological properties.