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5-Carboxyfluorescein

5-Carboxyfluorescein Struktur
76823-03-5
CAS-Nr.
76823-03-5
Englisch Name:
5-Carboxyfluorescein
Synonyma:
5-FAM;5(6)-FAM;3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid;5-CF;4-carboxyfluorescein;5-Carboxyfluorescein (5-FAM);5-(AND-6)-CARBOXY SNARF(R)-1;3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid;TQSY001;Fam (dye)
CBNumber:
CB1201921
Summenformel:
C21H12O7
Molgewicht:
376.32
MOL-Datei:
76823-03-5.mol

5-Carboxyfluorescein Eigenschaften

Schmelzpunkt:
368-372°C
Siedepunkt:
725.2±60.0 °C(Predicted)
Dichte
1.73±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
L?slichkeit
DMF: soluble
Aggregatzustand
Solid
pka
3.3, 4.6, 6.4, 7.0(at 25℃)
Farbe
Yellow to orange
S?ure-Base-Indikators(pH-Indikatoren)
Weak green ' uorescence (6.0) to strong green ' uourescence (7.2)
maximale Wellenl?nge (λmax)
492nm
BRN 
57037
Biologische Anwendungen
Authenticating canned products; detecting/measuring citrate; as a substrate for measuring phospholipase activity; use in ophthalmology
Major Application
Fluorescent probe, diagnosis of cancer, leukemia, colorectal cancer, polynucleotide, bacteria, pathogens, nucleic acid, hepatitis A virus, dengue virus, herpes simplex virus, gene, HIV type, cardiovascular risk factor
InChI
1S/C21H12O7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)21(15)14-4-1-10(19(24)25)7-13(14)20(26)28-21/h1-9,22-23H,(H,24,25)
InChIKey
NJYVEMPWNAYQQN-UHFFFAOYSA-N
SMILES
OC(=O)c1ccc2c(c1)C(=O)OC23c4ccc(O)cc4Oc5cc(O)ccc35
CAS Datenbank
76823-03-5(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi
R-S?tze: 36
S-S?tze: 26-39
WGK Germany  3
8
HS Code  32129000
Speicherklasse 11 - Combustible Solids
Bildanzeige (GHS) Exclamation Mark (GHS07)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.
P337+P313 Bei anhaltender Augenreizung: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.

5-Carboxyfluorescein Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

5-Carboxyfluorescein is a single isomer derivative of 5(6)-carboxyfluorescein that can be used to fluorescently label biomolecules through the interaction of carboxylic acid with primary amines. It demonstrates excitation/emission maxima of 492 and 518 nm, respectively.

Chemische Eigenschaften

Orange Solid

Verwenden

5-Carboxyfluorescein(5-FAM) contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. It 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. It has been principally used to develop a variety of green fluorescent reagents and small fluorescent molecules due to its relatively high absorbance characteristics, excellent fluorescence quantum yield, and good water solubility. The probe has also found application in studies of liposome-cell, cell-cell, and liposome-liposome interactions and in related studies on lipid bilayer structures.

Definition

ChEBI: 5-carboxyfluorescein is a monocarboxylic acid. It has a role as a fluorochrome. It is functionally related to a fluorescein (lactone form).

Application

5-Carboxyfluorescein (5-FAM) is one of the most widely used fluorescent dyes. Its excitation spectrum peak (EXmax) is at 492 nm, whilst its fluorescence emission spectrum peak (EMmax) is at 518 nm; it possesses a high quantum yield and is used for labelling oligonucleotides [2]. 5-FAM is a green fluorescent compound containing a single carboxyl group, which can be used as a detection substrate for OAT1 and OAT3. Its fluorescence intensity is extremely sensitive to pH. In acidic conditions (pH < 6), its fluorescence is significantly quenched; it is suitable for use in weakly alkaline buffers with a pH of 7.5–9.0.

Biochem/physiol Actions

5-Carboxyfluorescein is used for the staining of cells to differentiate between live and dead cells. It helps in monitoring the integrity and intactness of the cell membrane. It is also used for the measurement of intracellular pH. 5-Carboxyfluorescein diacetate is a non-fluorescent molecule which is cleaved by intracellular esterases, thereby giving a green fluorescent product 5-carboxyfluorescein. In viable cells, the fluorescent molecule is impermeable to the cellular membrane.

Synthese

5-Carboxyfluorescein is a mixture of 5- and 6-isomers prepared by the reaction of benzotricarboxylic anhydride with resorcinol and zinc chloride.
Reaction: 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°C 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°C. This residue was recrystallized two times from methanol/hexane to give 1.0 g of 6-carboxyfluorescein methanesulfonic acid adduct 2b. 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 2a.
Preparation of 5- and 6-Carboxyfluorescein
The methane sulfonic esters 2 are easily converted to the 5- and 6-carboxyfluoresceins 1 by treatment with sodium hydroxide solution then neutralizing with aqueous HCl.

5-Carboxyfluorescein Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


5-Carboxyfluorescein Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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76823-03-5()Verwandte Suche:


  • 5-CARBOXYLUORESCEIN
  • 4-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-isophth
  • 3',6'-dihydroxy-3-keto-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid
  • 5-Carboxyfluorescein Hydrate
  • 5-FAM, 5-CF
  • 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic Acid
  • 5-FAM, 4-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-isophthalic acid
  • 3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
  • Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylicacid, 3',6'-dihydroxy-3-oxo-
  • 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid
  • TQSY001
  • 5-Carboxyfluorescein, Single isomer
  • 5-(AND-6)-CARBOXY SNAFL(R)-1
  • 5-(AND-6)-CARBOXY SNAFL(R)-2
  • 5-(AND-6)-CARBOXYFLUORESCEIN
  • 5-CARBOXYFLUORESCEIN
  • 4-(6-HYDROXY-3-OXO-3H-XANTHEN-9-YL)-ISOPHTHALIC ACID
  • 5-carboxy' Uorescein
  • Fam (dye)
  • Fam 494/520
  • 5-FAM [5-Carboxyfluorescein] *CAS 76823-03-5*
  • 5-Carboxyfluorescein Hydrate>
  • Carboxyfluorescein Carboxyfluorescein
  • 4-carboxyfluorescein
  • 5-Carboxyfluorescein (5-FAM)
  • 5(6)-FAM
  • 5-(AND-6)-CARBOXY SNARF(R)-1
  • 5-CF
  • 5-FAM (5-Carboxyfluorescein), Amine-reactive fluorescent label
  • 5-FAM, 10 mM in DMSO
  • 5(6)-FAM [5-(and-6)-Carboxyfluorescein] UltraPure Grade Mixed Isomers
  • 5-Carboxyfluorescein (Technical Grade)
  • 5-FAM (Green)
  • 3',6'-dihydroxy-3-oxy-3H-spiro[isobenzofuran-1,9'-oxyanthracene]-5-carboxylic acid
  • 3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid , 5-FAM
  • 3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid
  • 3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
  • 5-FAM
  • 76823-03-5
  • C21H12O7xH2O
  • Biochemicals and Reagents
  • BioChemical
  • Fluorescent Probes, Labels, Particles and Stains
  • Detection
  • Fluorescent
  • Xanthene
  • marker
  • Fluorescent Labels & Indicators
  • FLUOROPHORES
  • FAM
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