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76823-03-5 molecular structure
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3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid

ChemBase ID: 130878
Molecular Formular: C21H12O7
Molecular Mass: 376.31578
Monoisotopic Mass: 376.05830272
SMILES and InChIs

SMILES:
c1cc2c(cc1C(=O)O)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
Canonical SMILES:
Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)C(=O)O)ccc(c1)O
InChI:
InChI=1S/C21H12O7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)21(15)14-4-1-10(19(24)25)7-13(14)20(26)28-21/h1-9,22-23H,(H,24,25)
InChIKey:
NJYVEMPWNAYQQN-UHFFFAOYSA-N

Cite this record

CBID:130878 http://www.chembase.cn/molecule-130878.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
IUPAC Traditional name
5-carboxyfluorescein
Synonyms
3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic Acid
5-Carboxyfluorescein
5-FAM
5-Carboxyfluorescein
CAS Number
76823-03-5
MDL Number
MFCD00036874
Beilstein Number
57037
PubChem SID
24888769
24892258
162225156
PubChem CID
123755

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 123755 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.8326864  H Acceptors
H Donor LogD (pH = 5.5) 1.8670381 
LogD (pH = 7.4) 0.27040523  Log P 3.5379257 
Molar Refractivity 98.4763 cm3 Polarizability 36.786808 Å3
Polar Surface Area 113.29 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMF: soluble expand Show data source
DMSO expand Show data source
DMSO: soluble expand Show data source
H2O: soluble expand Show data source
Methanol expand Show data source
Apperance
Orange Solid expand Show data source
Melting Point
>300°C expand Show data source
Fluorescence
λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
99% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for fluorescence expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C21H12O7 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 86826 external link
Other Notes
Derivative of fluorescein giving stable derivative upon conjugation with biopolymers1,2
Toronto Research Chemicals - C178320 external link
A useful reagent for the preparation of hydrolytically stable fluorescent conjugates and is a useful starting material for the synthesis of other fluorescein-derives reagent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Theisen, P., et al.: Tetrahedron Lett., 33, 5033 (1992)
  • • Mattingly, P.: Bioconjgate Chem., 3, 430 (1992, Bertrand, R., et al.: Biochemistry, 34, 9500 (1995)
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PATENTS

PATENTS

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INTERNET

INTERNET

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