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3326-34-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:102444 http://www.chembase.cn/molecule-102444.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem
Acid pKa 8.719013  H Acceptors
H Donor LogD (pH = 5.5) 3.0507562 
LogD (pH = 7.4) 3.0309548  Log P 3.0514169 
Molar Refractivity 95.9205 cm3 Polarizability 35.55254 Å3
Polar Surface Area 102.01 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
Methanol expand Show data source
Apperance
Dark Red Solid expand Show data source
Melting Point
223 °C (dec.)(lit.) expand Show data source
Absorption Wavelength
λmax 496 nm expand Show data source
Storage Condition
2-8°C, Desiccate expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Purity
≥90% (HPLC) expand Show data source
Grade
for fluorescence expand Show data source
p.a. expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Impurities
≤1% 6-isomer (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C20H13NO5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05209359 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02101709 external link
Dark Red (for synthesis of Fluorescein Isothiocyanate)
Sigma Aldrich - 201626 external link
Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Sigma Aldrich - 07980 external link
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 external link
Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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