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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 2321-07-5
• EC Number: 219-031-8
• MDL Number: MFCD00005050
• Beilstein Number: 94324
• Merck Index: 144159
• PubChem SID: 24894822; 24859566; 24870483; 46504703; 160964038
• 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: 45350:1; 45350

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.719013
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8800821
• LogD (pH = 7.4): 3.8598857
• Log P: 3.8803427
• Molar Refractivity: 91.2201 cm^3
• Polarizability: 34.4024 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.64
• LOG S: -4.11
• Solubility (Water): 2.55e-02 g/l

PROPERTIES

Physical Property

• Solubility: 600 mg/mL (sodium salt); DMSO; Slightly in water
• Apperance: Red Solid
• Melting Point: >300°C; 314 - 316°C; 320 °C(lit.); 320°C
• Density: 1.602 g/mL
• Absorption Wavelength: λmax 496 nm
• Hydrophobicity(logP): 3.4

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: LM5075000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36; R:36
• Safety Statements: 26; 26-60; S:26; S26 S36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PTPN1(5770), PTPRF(5792)

Product Information

• Purity: ~96%; 90+%; 95+%
• Grade: Reag. Ph. Eur.
• Compostion: Dye content, 95%
• Suitability: in accordance for electrophoresis test; in accordance for TLC; passes test for TLC; passes test for UV spectrum
• Ignition Residue: ≤0.25% (as SO4)
• Usage: sufficient for 100 tests
• Empirical Formula (Hill Notation): C20H12O5

DETAILS

MP Biomedicals - 02151155

C.I. 45350.1
Free Acid
Crystalline
Purity: ~96%

DrugBank - DB00693

• 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

Packaging
2.5, 100, 500 g in glass bottle

Sigma Aldrich - 46978

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

General description
Visit our Titration Center to learn more.

Toronto Research Chemicals - F485250

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

• 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)