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

• ChemBase ID: 102444
• Molecular Formular: C20H13NO5
• Molecular Mass: 347.32092
• Monoisotopic Mass: 347.07937252
• SMILES: Nc1cc2c(cc1)C1(OC2=O)c2c(Oc3c1ccc(O)c3)cc(O)cc2
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)N)ccc(c1)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 5-amino-3',6'-dihydroxyspiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: 5-Aminofluorescein; FLUORESCEIN AMINE ISOMER I; 1-AMINOFLUORESCEIN; Fluoresceinamine, Isomer 1; Fluoresceinamine isomer I; 5-Aminofluorescein; Fluoresceinamine, isomer I

Database IDs

• CAS Number: 3326-34-9
• EC Number: 222-043-6
• MDL Number: MFCD00005052
• Beilstein Number: 48395
• PubChem SID: 162088661; 24852015
• PubChem CID: 76845

CALCULATED PROPERTIES

• Acid pKa: 8.719013
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.0507562
• LogD (pH = 7.4): 3.0309548
• Log P: 3.0514169
• Molar Refractivity: 95.9205 cm^3
• Polarizability: 35.55254 Å^3
• Polar Surface Area: 102.01 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Dark Red Solid
• Melting Point: 223 °C (dec.)(lit.)
• Absorption Wavelength: λmax 496 nm

Safety Information

• Storage Condition: 2-8°C, Desiccate
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥90% (HPLC)
• Grade: for fluorescence; p.a.
• Impurities: ≤1% 6-isomer (HPLC)
• Empirical Formula (Hill Notation): C20H13NO5

DETAILS

MP Biomedicals - 05209359

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101709

Dark Red (for synthesis of Fluorescein Isothiocyanate)

Sigma Aldrich - 201626

Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 07980

Application
The two isomers are produced by the usual synthesis. Most publications imply they are interchangeable when used for the preparation of the isothiocyanate for fluorescent antibody work. In fact, most commercial preparations are not even labeled as to whether or not they are mixtures.
Other Notes
All known glycosaminoglycuronans react with this fluorescein derivative to yield fluorescent derivatives1
Note: Do not confuse with fluorescamine.

Toronto Research Chemicals - F485300

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)