ContaminantDB: Fluorescein

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:17:30 UTC

Update Date

2026-03-26 21:52:37 UTC

Accession Number

CHEM003765

Identification

Common Name

Fluorescein

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Contrast Media
Drug
Ester
Ether
Fluorescent Dye
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3',6'-Dihydroxyfluoran	ChEBI
3,6-Fluorandiol	ChEBI
9-(O-Carboxyphenyl)-6-hydroxy-3-isoxanthenone	ChEBI
9-(O-Carboxyphenyl)-6-hydroxy-3H-xanthen-3-one	ChEBI
C.I. 45350	ChEBI
C.I. solvent yellow 94	ChEBI
D And C yellow no. 7	ChEBI
D&C yellow no. 7	ChEBI
Fluoresceine	ChEBI
Fluoreszein	ChEBI
Japan yellow 201	ChEBI
Resorcinolphthalein	ChEBI
Solvent yellow 94	ChEBI
Yellow fluorescein	ChEBI
Fluorescite	Kegg
2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid	HMDB
D And C yellow no. 8	HMDB
Fluor I strip a.t.	HMDB
Fluorescein, disodium	HMDB
Disodium fluorescein	HMDB
Disodium salt, fluorescein	HMDB
Fluorescein monosodium salt	HMDB
Fluorescein sodium, minims	HMDB
Fluoresceine, minims	HMDB
Ful glo	HMDB
Funduscein	HMDB
Optifluor diba	HMDB
Uranine	HMDB
Colircusi fluoresceina	HMDB
Fluor-I-strip a.t.	HMDB
Fluorescéine sodique faure	HMDB
Ful-glo	HMDB
Minims fluorescein sodium	HMDB
Minims stains	HMDB
Fluorescein, sodium	HMDB
Fluoresceina, colircusi	HMDB
Fluorets	HMDB
Monosodium salt, fluorescein	HMDB
Sodium fluorescein	HMDB
Diofluor	HMDB
Dipotassium salt, fluorescein	HMDB
Fluorescein dipotassium salt	HMDB
Fluorescein disodium salt	HMDB
Fluorescein sodium	HMDB
Minims fluoresceine	HMDB
Sodium, fluorescein	HMDB

Chemical Formula

C₂₀H₁₂O₅

Average Molecular Mass

332.306 g/mol

Monoisotopic Mass

332.068 g/mol

CAS Registry Number

2321-07-5

IUPAC Name

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

Traditional Name

fluorescein

SMILES

OC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C1

InChI Identifier

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

InChI Key

GNBHRKFJIUUOQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Diaryl ether
Benzofuranone
Phthalide
Isobenzofuranone
Isobenzofuran
Isocoumaran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthene dye (CHEBI:31624 )
polyphenol (CHEBI:31624 )
gamma-lactone (CHEBI:31624 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	315 dec°C
Boiling Point	Not Available
Solubility	600 mg/mL (sodium salt)

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.64	ALOGPS
logP	3.88	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.22 m³·mol⁻¹	ChemAxon
Polarizability	33.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-1353900000-611445d6ab5246bd851e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-2290000000-eaff9e9aba714ba94d70	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0090000000-074ba8ce3e0f48eac1d4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-1353900000-611445d6ab5246bd851e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0293000000-5c35ecc919b17d5620ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6209500000-ab23980f2cb4a151abfd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0f80-0190000000-96c116d14e45c092e3f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0udi-0290000000-944ad92942eac5b0f55f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-0090000000-204c801c10d3ba0033ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-001i-0039000000-d0fed4e679a1e2dc78c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-0009000000-672d3730ba6ae79ee546	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-001r-0097000000-67a600d065bee725a05f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0009000000-6567ba7d3ba05b9d01d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-c316a18c3fdc7e099efa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-000i-0090000000-84665b22751248226f52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-000i-0090000000-a6509aa14ca177154363	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000i-0090000000-c3e2a008fb7411e3a84a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-000i-0090000000-cd13dbf3066c7e4ffcd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-410e3782a3377a462731	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0019000000-1289e7fde734685fd3a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3091000000-652abda58542de821938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0019000000-9f41afc4f708c3e148c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-0098000000-53c4786408b95271c9e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0090000000-40b0e641661193aac8a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-f4f678f3c48d6f43d1c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-f4f678f3c48d6f43d1c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0094000000-ce67e0891aa59a25f4c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-69a3ee786a10c930b443	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0029000000-7b8b5113b7dd9ac05ef2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-5396000000-4bc93173d30ee8ba9c96	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly distributed

Mechanism of Toxicity

Fluorescein sodium is used extensively as a diagnostic tool in the field of ophthalmology. Fluorescein is a fluorescent compound or fluorophore having a maximum absorbance of 494 m and an emission maximum of 521 nm. The yellowish-green fluorescence of the compound can be used to demarcate the vascular area under observation, distinguishing it from adjacent areas. It is applied topically in the form of a drop or it can be injected intravenously to produce a fluorescein angiogram. Topical fluorescein is a useful tool in the diagnosis of corneal abrasions, corneal ulcers, herpetic corneal infections, and dry eye. Fluorescein angiography is used to diagnose and categorize macular degeneration, diabetic retinopathy, inflammatory intraocular conditions, and intraocular tumors.

Metabolism

Route of Elimination: Fluorescein and its metabolites are mainly eliminated via renal excretion.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00693

HMDB ID

HMDB0014831

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Richard T. Dean, Conrad P. Dorn, Jr., Tsung-Ying Shen, “Fluorescein esters and ethers and the preparation thereof.” U.S. Patent US4304720, issued January, 1972.

MSDS

Link

General References

1. Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31.

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1517825

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15465055

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16195545

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20371259

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2508085

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26756394

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7868912

Fluorescein (CHEM003765)

Structure for CHEM003765: Fluorescein