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2321-07-5 molecular structure
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3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

ChemBase ID: 575
Molecular Formular: C20H12O5
Molecular Mass: 332.30628
Monoisotopic Mass: 332.06847348
SMILES and InChIs

SMILES:
O1C2(c3c(C1=O)cccc3)c1c(Oc3c2ccc(O)c3)cc(O)cc1
Canonical SMILES:
Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)O
InChI:
InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
InChIKey:
GNBHRKFJIUUOQI-UHFFFAOYSA-N

Cite this record

CBID:575 http://www.chembase.cn/molecule-575.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
IUPAC Traditional name
fluorescein
Brand Name
Acid Yellow 73
Eosin
Fluorescein Sodium salt
Fluorescein acid
Fluorescein disodium salt
Fluorescein disodium salt dihydrate
Fluorescein sodium
Fluorescein, Disodium Salt, Fluorescein, disodium salt
Fluorescite
Funduscein-25
Uranin
Uranine
Synonyms
3',6'-Dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one
3',6'-Dihydroxyfluoran
2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic Acid
C.I. 45350:1
C.I. Solvent Yellow 94
D and C Yellow No. 7
D&C Yellow No. 7
Fluorescein Acid
Japan Yellow 201
Japan Yellow No. 201
NSC 667256
Yellow Fluorescein
3',6'-Dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one
3',6'-Fluorandiol
3,6-Dihydroxyspiro[xanthene-9,3'-phthalide]
9-(o-Carboxyphenyl)-6-hydroxy-3-isoxanthenone
C.I. 45350.1
Fluorescein
Deoxyribonucleic acid
Fluorescein Low Range DNA standard
Fluorescein
Fluorescein (free acid)
Solvent Yellow 94
Acid Yellow 73
Fluorescein
resorcinolphthalein
C.I. 45350, solvent yellow 94, D & C yellow no. 7, angiofluon
Japan yellow 201, soap yellow
酸性黄 73
荧光素
CAS Number
2321-07-5
EC Number
219-031-8
MDL Number
MFCD00005050
Beilstein Number
94324
Merck Index
144159
PubChem SID
24859566
24870483
46504703
160964038
24894822
PubChem CID
16850
CHEBI ID
31624
CHEMBL
177756
Chemspider ID
15968
DrugBank ID
DB00693
KEGG ID
D01261
MeSH Name
Fluorescein
Unique Ingredient Identifier
TPY09G7XIR
Wikipedia Title
Fluorescein
Color Index Number
45350
45350:1

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.719013  H Acceptors
H Donor LogD (pH = 5.5) 3.8800821 
LogD (pH = 7.4) 3.8598857  Log P 3.8803427 
Molar Refractivity 91.2201 cm3 Polarizability 34.4024 Å3
Polar Surface Area 75.99 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.64  LOG S -4.11 
Solubility (Water) 2.55e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
600 mg/mL (sodium salt) expand Show data source
DMSO expand Show data source
Slightly in water expand Show data source
Apperance
Red Solid expand Show data source
Melting Point
>300°C expand Show data source
314 - 316°C expand Show data source
320 °C(lit.) expand Show data source
320°C expand Show data source
Density
1.602 g/mL expand Show data source
Absorption Wavelength
λmax 496 nm expand Show data source
Hydrophobicity(logP)
3.4 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
LM5075000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) 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
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36 expand Show data source
R:36 expand Show data source
Safety Statements
26 expand Show data source
26-60 expand Show data source
S:26 expand Show data source
S26 S36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P280-P264-P305+P351+P338-P337+P313 expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... PTPN1(5770), PTPRF(5792) expand Show data source
Purity
~96% expand Show data source
90+% expand Show data source
95+% expand Show data source
Grade
Reag. Ph. Eur. expand Show data source
Compostion
Dye content, 95% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
in accordance for electrophoresis test expand Show data source
in accordance for TLC expand Show data source
passes test for TLC expand Show data source
passes test for UV spectrum expand Show data source
Ignition Residue
≤0.25% (as SO4) expand Show data source
Usage
sufficient for 100 tests expand Show data source
Empirical Formula (Hill Notation)
C20H12O5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02151155 external link
C.I. 45350.1
Free Acid
Crystalline
Purity: ~96%
DrugBank - DB00693 external link
Item Information
Drug Groups approved
Description A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium, such as the aqueous humor, and is used therapeutically as a diagnostic aid in corneal injuries and corneal trauma. It has been approved by FDA for use in externally applied drugs and cosmetics. (From Merck Index, 12th ed; American Medical Association Drug Evaluations; 1995, p2275)
Indication For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
Affected Organisms
Humans and other mammals
Absorption Rapidly distributed
Protein Binding 85%
Elimination Fluorescein and its metabolites are mainly eliminated via renal excretion.
Distribution * 0.5 L/kg
Clearance * renal cl=1.75 mL/min/kg [After IV administration]
* hepatic cl=1.50 mL/min/kg [After IV administration]
References
Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. [Pubmed]
External Links
Wikipedia
RxList
Sigma Aldrich - F2456 external link
Packaging
2.5, 100, 500 g in glass bottle
Sigma Aldrich - 46978 external link
Components
1 vial pBR 322 Hin F1 digest in 10 mM TRIS, pH 8.0, 1 mM EDTA (50 fmol/μl each fragment; 0.14 μg/μl), 200 μl1 vial 5× loading buffer (12.5% Ficoll, 0.05% bromophenol blue, 50 mM TRIS, pH 8.0, 5 mM EDTA), 500 μl
General description
pBR 322 Hin F1 digest, 10 Fluorescein end-labeled fragments: 75, 154, 220/221, 296, 334, 396, 504, 517, 1632 bpdetection: Exc.: 302 nm, Em.: 521 nm
Sigma Aldrich - 32615 external link
General description
Visit our Titration Center to learn more.
Toronto Research Chemicals - F485250 external link
A fluorescent tracer used for many applications. It is used in ophthalmology as a tool in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It can attach to certain biologically active molecules, thus allowing biologists

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. Pubmed
  • • Drees, B.L. et al.: J. Biol. Chem., 271, 32168 (1996)
  • • Can. Med. Assoc. J., 80, 997 (1996)
  • • Taki, M. et al.: Prot. Eng. Des. Select., 17, 119 (1996)
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PATENTS

PATENTS

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INTERNET

INTERNET

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