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HomeProduct name list6-Carboxyfluorescein

6-Carboxyfluorescein

Synonym(s):6-Carboxyfluorescein;6-FAM;FLUOS

  • CAS NO.:3301-79-9
  • Empirical Formula: C21H12O7
  • Molecular Weight: 376.32
  • MDL number: MFCD00036873
  • EINECS: 636-503-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-01 18:44:47
6-Carboxyfluorescein Structural

What is 6-Carboxyfluorescein?

Chemical properties

Orange Solid

The Uses of 6-Carboxyfluorescein

6-Carboxyfluorescein is derivative of fluorescein giving stable derivative upon conjugation with biopolymers.It has been used to check the plasma membrane integrity in sperm cells.

What are the applications of Application

6-Carboxyfluorescein is a carboxylated fluorescein dye

Preparation

1,2,4-Benzenetricarboxylic anhydride (also called 4- carboxyphthalic anhydride, 25.0 g, 0.13 mol) was added to a solution of 1,3-dihydroxybenzene (also called resorcinol, 28.6 g, 0.26 mol) in methane sulfonic acid (1M). An air condenser was attached to the flask and the reaction was heated at 85 oC in an open vessel for 24 h. After cooling to room temperature, the reaction mixture was poured into 7 volumes of ice/water. An orange-yellow precipitate formed; this was collected by filtration and dried in an oven at 200 oC. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6- carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes. The mother liquors from this procedure were collected, the solvent was removed in vacuo, and the residues were recrystallized two times from ethanol/hexanes to give 3.2 g of 5-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from EtOH/hexanes. Finally, the mother liquors from this experiment were combined, evaporated to dryness, and recrystallized two times from methanol/hexanes to give another 3.0 g of 6-carboxyfluorescein methanesulfonic acid adduct preferentially crystallizes from MeOH/hexanes, making a total yield of 4.0 g, 40 %. Careful dropwise addition of conc. HCl(aq) to solutions of these methanesulfonic esters preferentially crystallizes from EtOH/hexanes and preferentially crystallizes from MeOH/hexanes in 4M sodium hydroxide gave 5-carboxyfluorescein and 6-carboxyfluorescein, respectively in near quantitative yield.

Definition

ChEBI: 6-carboxyfluorescein is a monocarboxylic acid. It derives from a fluorescein (lactone form).

What are the applications of Application

6-Carboxyfluorescein is a useful reagent for the preparation of hydrolytically stable fluorescent conjugates and is a useful starting material for the synthesis of other fluorescein-derives reagent. Fluorescein is the most common fluorescent derivatization reagent for labeling biomolecules. In addition to its relatively high absorptivity, excellent fluorescence quantum yield, and good water solubility, fluorescein has an excitation maximum that closely matches the 488 nm spectral line of the argon-ion laser.

Biochem/physiol Actions

6-Carboxyfluorescein diacetate is a membrane permeable compound. It can be hydrolysed by intracellular esterases to form a membrane impermeable bright green fluorescent molecule, 6-carboxyfluorescein.

Properties of 6-Carboxyfluorescein

Melting point: >300 °C(lit.)
Boiling point: 736.4±60.0 °C(Predicted)
Density  1.73±0.1 g/cm3(Predicted)
storage temp.  Sealed in dry,2-8°C
solubility  DMSO: soluble
form  Solid
pka 3.3, 4.6, 6.4, 7.0(at 25℃)
color  Yellow to orange
PH Range Weak green ' uorescence (6.0) to strong green ' uourescence (7.2)
λmax 492nm
BRN  54341
Major Application Diagnosis of hematologic cancer, nongastric diseases, detection of genetically modified wheat, chromosomes, gene expression, nucleic acid, hepatitis A virus, avian influenza virus subtype H5 and H5N1, SARS virus, herpex simplex virus
Biological Applications Diagnosing bladder cancer; evaluating corneal endothelial barrier function; as a substrate for measuring protein kinase activity, methyltransferase activity, phospholipase activity, rhodanese activity,sulfotransferase activity;use in ophthalmology
CAS DataBase Reference 3301-79-9(CAS DataBase Reference)
EPA Substance Registry System Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxylic acid, 3',6'-dihydroxy-3-oxo- (3301-79-9)

Safety information for 6-Carboxyfluorescein

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 6-Carboxyfluorescein

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