5-Amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoesure
FLUORESCEINAMINE · 5-AF · AMINOFLUORESCEIN · 5-AFM · 4-AMINOFLUORESCEIN · 5-amino-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one · 5-AMF · (isoMer I)
Identifikatoren & physikalische Daten
| CAS No. | 3326-34-9 |
|---|---|
| Summenformel | C20H13NO5 |
| Durchschnittliche Molmasse | 347,3 g/mol |
| Monoisotopische Masse | 347,07937252 g/mol |
| SMILES | Nc1ccc2c(c1)C(=O)OC21c2ccc(O)cc2Oc2cc(O)ccc21 |
| InChIKey | GZAJOEGTZDUSKS-UHFFFAOYSA-N |
| PubChem CID | 76845 |
| ChEMBL | CHEMBL5284644 |
| ChEBI | CHEBI:91078 |
| EC No. | 222-043-6 |
| DTXSID | DTXSID0062979 |
| Lokaler Name | 5-Amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoesure |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 102 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 557 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 223 °C (dec.)(lit.) |
| Siedepunkt | 481.89°C (rough estimate) |
| Dichte | 1.3724 (rough estimate) |
| Brechungsindex | 1.5180 (estimate) |
| Lagerbedingungen | room temp |
| Löslichkeit | DMF: 5 mg/mlDMSO: 5 mg/mlSoluble in water (partly), methanol (10 mg/ml), and acetone. |
| pKa (Säurekonstante) | 9.34±0.20(Predicted) |
| Aggregatzustand | powder |
| Farbe | red-brown |
| BRN | 48395 |
| Stabilität | Light and Moisture Sensitive |
| Hauptanwendungen | diagnostic assay manufacturinghematologyhistology |
| InChI | 1S/C20H13NO5/c21-10-1-4-14-13(7-10)19(24)26-20(14)15-5-2-11(22)8-17(15)25-18-9-12(23)3-6-16(18)20/h1-9,22-23H,21H2 |
| InChIKey | GZAJOEGTZDUSKS-UHFFFAOYSA-N |
| SMILES | Nc1ccc2c(c1)C(=O)OC23c4ccc(O)cc4Oc5cc(O)ccc35 |
| CAS Datenbank | 3326-34-9(CAS DataBase Reference) |
| EPA chemische Informationen | Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 5-amino-3',6'-dihydroxy- (3326-34-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (98.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 85 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (98.8%) |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 32049090 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
Glycosaminoglycuronans react with 5-aminofluorescein to yield fluorescent derivatives. 5-aminofluorescein is also used to prepare FITC Isomer I (F-011, F-020).
Herstellung & Synthese
synthetische
The preparation of 5-aminofluorescein is carried out either by first saponification of 5-nitrofluorescein acetates with alcohol alkali, followed by reduction of the obtained 5-nitrofluorescein in a solution of alcohol alkali with hydrazine hydrate on a nickel catalyst to obtain 5-aminofluorescein , Or by boiling in an aqueous solution of sodium sulfide. The restoration of the nitro group and the saponification of acetates in the second case occurs in one stage.