6-amino-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase ID: 107077
• Molecular Formular: C20H13NO5
• Molecular Mass: 347.32092
• Monoisotopic Mass: 347.07937252
• SMILES: Nc1cc2c(cc1)C(=O)OC12c2c(Oc3c1ccc(O)c3)cc(O)cc2
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cc(N)cc2)ccc(c1)O
• InChI: InChI=1S/C20H13NO5/c21-10-1-4-13-16(7-10)20(26-19(13)24)14-5-2-11(22)8-17(14)25-18-9-12(23)3-6-15(18)20/h1-9,22-23H,21H2
• InChIKey: YOAWSYSKQHLFPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 6-amino-3',6'-dihydroxyspiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: 2-AMINOFLUORESCEIN; 6-Aminofluorescein; 6-Amino-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; Fluoresceinamine, Isomer 2,; Fluoresceinamine isomer II; 6-Aminofluorescein

Database IDs

• CAS Number: 51649-83-3
• EC Number: 257-334-7
• MDL Number: MFCD00005051
• Beilstein Number: 51708
• PubChem SID: 162092941; 24852016
• PubChem CID: 103924

CALCULATED PROPERTIES

• Acid pKa: 8.719012
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.0509143
• LogD (pH = 7.4): 3.0309567
• Log P: 3.0514169
• Molar Refractivity: 95.9205 cm^3
• Polarizability: 35.551857 Å^3
• Polar Surface Area: 102.01 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Methanol
• Apperance: Yellow to Orange Solid
• Melting Point: 285 °C (dec.)(lit.); 297-302°C (dec.)
• Absorption Wavelength: λmax 495 nm

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C20H13NO5

DETAILS

MP Biomedicals - 05202463

MP Biomedicals Rare Chemical collection

Sigma Aldrich - F7125

Other Notes
Note: Do not confuse with fluorescamine.
Application
6-Aminofluorescein has been demonstrated to be useful fluorescent labeling reagent for fullerene-based liposome nanostructures termed ‘buckysomes’1. 6-aminofluorescein dissolved in 0.1 N NaOH can be quantified from a maximum absorbance at 490 nm. Decarboxylated 6-aminofluorescein dissolved 6 N HCl (prepare by constant boiling at 110° C for 24 h) can be quantified from a maximum absorbance at 454 nm. Aldehyde groups are formed by oxidateive damage to proteins, which can be detected by conjugation to decarboxylated 6-aminofluorescein2.

Sigma Aldrich - 201634

Other Notes
Note: Do not confuse with fluorescamine.
Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application
6-Aminofluorescein has been demonstrated to be useful fluorescent labeling reagent for fullerene-based liposome nanostructures termed ‘buckysomes’1. 6-aminofluorescein dissolved in 0.1 N NaOH can be quantified from a maximum absorbance at 490 nm. Decarboxylated 6-aminofluorescein dissolved 6 N HCl (prepare by constant boiling at 110° C for 24 h) can be quantified from a maximum absorbance at 454 nm. Aldehyde groups are formed by oxidateive damage to proteins, which can be detected by conjugation to decarboxylated 6-aminofluorescein2.

Toronto Research Chemicals - F485325

Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens.

REFERENCES

• Riggs, H.J.L., et al.: Amer. J. Pathol., 34, 1081 (1958)
• Mann, K.G. and Fish, W.W., Methods in Enz., 26, 28 (1958)