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

• ChemBase ID: 102128
• Molecular Formular: C21H11NO5S
• Molecular Mass: 389.38074
• Monoisotopic Mass: 389.03579346
• SMILES: Oc1cc2c(cc1)C1(OC(=O)c3c1ccc(c3)N=C=S)c1c(O2)cc(O)cc1
• Canonical SMILES: S=C=Nc1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• InChI: InChI=1S/C21H11NO5S/c23-12-2-5-16-18(8-12)26-19-9-13(24)3-6-17(19)21(16)15-4-1-11(22-10-28)7-14(15)20(25)27-21/h1-9,23-24H
• InChIKey: MHMNJMPURVTYEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3',6'-dihydroxy-5-isothiocyanato-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: FITC
• Synonyms: Fluorescein 5-isothiocyanate; Fluorescein isothiocyanate isomer I; Fluorescein 5-Isothiocyanate, Isomer 1, 95%; Fluorescein-5-Isothiocyanate; FITC; FLUORESCEIN ISOTHIOCYANATE ISOMER I

Database IDs

• CAS Number: 3326-32-7
• EC Number: 222-042-0
• MDL Number: MFCD00005063
• Beilstein Number: 1407295
• PubChem SID: 162088593; 24894823
• PubChem CID: 18730

CALCULATED PROPERTIES

• Molar Refractivity: 108.283 cm^3
• Polarizability: 40.097435 Å^3
• Polar Surface Area: 88.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 8.719013
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.901907
• LogD (pH = 7.4): 4.881711
• Log P: 4.9021683

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow to Light Orange solid
• Melting Point: >255°C (dec.); >360 °C(lit.); >360°C
• Absorption Wavelength: λmax 499 nm
• Fluorescence: λex 492 nm; λem 518 nm (green); λex 492 nm; λem 518 nm in 0.1 M phosphate pH 8.0

Safety Information

• Storage Condition: 0°C, Desiccate; -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC); 90%; 90% min.
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C21H11NO5S

DETAILS

MP Biomedicals - 02100276

Isomer I Purity: 90% min.
Suitable for protein labelling.

Sigma Aldrich - F2502

Application
Reagent for the FITC labeling of proteins; Microsequencing of proteins and peptides (HPLC)
Fluorescent labeling reagent for proteins.1,2,3,4,5 Used in the fluorescent antibody technique for rapid identification of pathogens.6,7
Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 46952

Application
Reagent for the FITC labeling of proteins; Microsequencing of proteins and peptides (HPLC)

Toronto Research Chemicals - F485700

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)