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Fluorescein sodium(CAS No. 518-47-8)

Fluorescein sodium C20H12O5?2Na (cas 518-47-8) Molecular Structure

518-47-8 Structure

Identification and Related Records

【Name】
Fluorescein sodium
【CAS Registry number】
518-47-8
【Synonyms】
Acid Yellow 73~C.I. 45350
C.I. 45350
Fluorescein Sodium Salt
Uranine
Fluorescein disodium salt hydrate
C.I. Acid Yellow 73
Acid Yellow 73 (C.I.)
disodium 2-(3-oxo-6-oxidoxanthen-9-yl)benzoate
Fluorescein
Acid Yellow 73
Uranin
11824 yellow
12417 yellow
ful-glo
funduscein
furanium
hidacid uranine
Soap yellow
C.I. 45350 sodium salt
sodium fluoresceinate
fluorescein sodium b.p
sodium salt of hydroxy-o-carboxy-phenyl-fluorone
resorcinol phthalein sodium
Fluorescein, sodium derivative, sodium salt
Soluble fluorescein
Uranine A Extra
Uranine K
Uranine O
Uranine SS
Uranine USP XII
Uranine WSS
Uranine Yellow
Yellow no. 8
3',6'-Dihydroxy-spiro[3H-isobenzofuran-1,9'-xanthen]-3-one disodium salt
3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-(9H)xanthene]-3-one, disodium salt
3,6-Dihydroxyxanthene-9-spiro-1'-3'H-isobenzofuran-3'-one
3,6-Dihydroxyxanthene-9-spiro-1'-3'H-isobenzofuran-3'-one dipotassium salt
3,6-Dihydroxyxanthene-9-spiro-1'-3'H-isobenzofuran-3'-one disodium salt
9-(o-Carboxyphenyl)-3,6-dihydroxyxanthylium dipotassium salt
9-(o-Carboxyphenyl)-3,6-dihydroxyxanthylium disodium salt
9-o-carboxyphenyl-6-hydroxy-3-isoxanthone, disodium salt
Acid Yellow 73
aizen uranine
Dihydroxyspiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one disodium salt
disodium 6-hydroxy-3-oxo-9-xanthene-o-benzoate
calcocid uranine b4315
certiqual fluoresceine
C.I. 45350 disodium salt
C.I. 766
d&c yellow no. 8
fluorescein, disodium salt
fluorescein, water soluble
Fluorescein W/S
fluor-i-strip a.t.
Fluorone
【EINECS(EC#)】
208-253-0
【Molecular Formula】
C20H12O5?2Na (Products with the same molecular formula)
【Molecular Weight】
376.27
【Inchi】
InChI=1/C20H12O5.2Na/c21-11-5-7-15-17(9-11)25-18-10-12(22)6-8-16(18)19(15)13-3-1-2-4-14(13)20(23)24;;/h1-10,21H,(H,23,24);;/q;2*+1/p-2
【Canonical SMILES】
C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
【MOL File】
518-47-8.mol

Chemical and Physical Properties

【Appearance】
orange powder
【Density】
1.601 g/cm3 (20 C)
【Melting Point】
320℃
【Boiling Point】
620.8oC at 760 mmHg
【Flash Point】
232.6 oC
【Water】
500 g/L (20℃)
【Solubilities】
Freely Souluble (600 g/l) SOLVENT
【Color/Form】
Red, orthorhombic prisms
Yellowish-red to red powder
Orange-red, crystalline powder
【Stability】
Stable.
【HS Code】
32041200
【Storage temp】
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
MAX ABSORPTION (DIOXANE): 225 NM (LOG E= 4.8); 227.5 NM (LOG E= 3.8); 490 NM (LOG E= 2.1)
Absorption max: 493.5, 460 nm
IR: 9792 (Sadtler Research Laboratories Prism Collection)
UV: 20876 (Sadtler Research Laboratories Spectral Collection)
【Computed Properties】
Molecular Weight:332.30628 [g/mol]
Molecular Formula:C20H12O5
XLogP3-AA:3.4
H-Bond Donor:2
H-Bond Acceptor:5
Rotatable Bond Count:0
Tautomer Count:5
Exact Mass:332.068473
MonoIsotopic Mass:332.068473
Topological Polar Surface Area:76
Heavy Atom Count:25
Formal Charge:0
Complexity:522
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Ring Count:5
Effective Rotor Count:0.4
Conformer Sampling RMSD:0.6
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36
【Safety Statements 】
S26;S37/39
【Safety】

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Human systemic effects by intravenous route: arrhythmias, eye hemorrhage, nausea or vomiting. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Na2O.
Hazard Codes:?IrritantXi
Risk Statements: 36-36/37/38?
R36: Irritating to eyes
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 22-24/25-37/39-26-36/37/39-27?
S22: Do not breathe dust
S24/25: Avoid contact with skin and eyes
S37/39: Wear suitable gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S27: Take off immediately all contaminated clothing
WGK Germany: 1
RTECS: LM5425000
F 3:?Hygroscopic
HS Code: 32041200

【Skin, Eye, and Respiratory Irritations】
Eye, skin, ... and/or respiratory tract irritation.
【Cleanup Methods】
Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately-labelled container for disposal. Wash spill site.
【Transport】
25kgs
【Fire Fighting Procedures】
Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials. This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity. As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
【Fire Potential】
This material is assumed to be combustible.
Slight.
【Formulations/Preparations】
Fluorescite (fluorescein injection, USP) 10% contains fluorescein sodium (equivalent to fluorescein 10% w/v.
Ak-Fluor (fluorescein injection, USP) 10% is 100 mg/mL in a 5 mL single vial and Ak-Fluor (fluorescein injection, USP) 25% is 250 mg/mL in a 2 mL single dose vial
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fluorescein sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Fluorescein sodium/
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Eye, skin, ... and/or respiratory tract irritation.
【Specification】

Handling?and?storge of Fluorescein sodium :
Handling: Wash thoroughly after handling. Use with adequate ventilation.Minimize dust generation and accumulation. Avoid ingestion and inhalation.Avoid contact with skin, eyes,and clothing. Keep container tightly closed.????
Storage: Keep container closed when not in use. Store in a cool, dry,well-ventilated area away from incompatible substances. Store protected from moisture.
?Fluorescein sodium (CAS NO.518-47-8) is also called as?9-(O-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one,disodiumsalt ; 9’-(9H)xanthen)-3-one,3’,6’-dihydroxy-spiro(isobenzofuran-1(3hdisodiums) ; 9’-[9H]xanthen]-3-one,3’,6’-dihydroxy-spiro[isobenzofuran-1(3hdisodiumsal ; 9-O-carboxyphenyl-6-hydroxy-3 isoxanthone,disodiumsalt ; Abcoluraninepowders&liquids ; Aizenuranine .

【Octanol/Water Partition Coefficient】
log Kow = 3.35 (est)
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Condensation of resorcinol with phthalic anhydride in the presence of zinc chloride
By heating phthalic anhydride and resorcinol.
... Fluorescein is manufactured by the acid condensation of resorcinol and phthalic acid or its anhydride.
U.S. Exports

(1986) ND
U.S. Imports

(1983) 2.07X10+6 /Acid Yellow 73/
U.S. Production

(1986) No Data
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 10 thousand - 500 thousand 1990 No Reports 1994 10 thousand - 500 thousand 1998 10 thousand - 500 thousand 2002 No Reports [US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Spiro[isobenzofuran-1(3H),9'-
【Usage】

Dye, ink pigment, in cosmetic products.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances used to allow enhanced visualization of tissues.
- Agents that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
【Therapeutic Uses】
Contrast Media
Fluorescein injection, (USP) 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature.
VET: Deep corneal ulcers, descemetocele, and iris prolapse are seen with some frequency in dogs, cats, and horses. ... Important diagnostic aids are the Schirmer tear test to measure aqueous tear production and topical fluorescein to examine the corneal ulcer. ...
... Fluorescein is applied topically in fitting of hard contact lenses ... also used to detect corneal epithelial defects ... to locate foreign bodies embedded in eye ... Also is instilled in eye to test lacrimal patency. /Fluorescein sodium/
Fluorescein is now sometimes used for determination of circulation time, adequacy of blood supply, and viability of tissue.
In determination of circulation time, ... by rapid iv ... appearance of fluorescence in lips, eyes, or intact skin or in wheals (histamine or scratch) ... is taken as end point.
Measurement of arm-to-retina circulation time is employed for diagnosis of carotid artery occlusion.
A diagnostic aid in ophthalmic angiography which includes examination of the fundus, evaluation of the iris vasculature, distinction between viable and nonviable tissue, and observation of the aqueous flow. It is useful in the differential diagnosis of malignant and nonmalignant ocular tumors. /Fluorescein sodium injection/
【Biomedical Effects and Toxicity】
Fluorescence of skin persists for several hr, and dye appears in urine for as long as 30 hr.
Within 7 to 14 seconds after IV administration into antecubital vein, fluorescein usually appears in the central artery of the eye. Within a few minutes of IV administration of fluorescein sodium, a yellowish discoloration of the skin occurs, which begins to fade after 6 to 12 hours of dosing. Various estimates of volume of distribution indicate that fluorescein distributes well into interstitial space (0.5 L/ kg).
Fluorescein and its metabolites are mainly eliminated via renal excretion. After IV administration, the urine remains slightly fluorescent for 24 to 36 hours. A renal clearance of 1.75 mL/min/kg and a hepatic clearance (due to conjugation) of 1.50 mL/min/kg have been estimated. The systemic clearance of fluorescein was essentially complete by 48 to 72 hours after administration of 500 mg fluorescein.
Fluorescein sodium has been demonstrated to be excreted in human milk.
The permeability of the blood-retinal and blood-aqueous barriers to fluorescein and the rate of aqueous flow can be estimated by measurements of fluorescein in the vitreous, aqueous, and plasma after systemic administration. Fluorescein is commonly measured by fluorescence, but fluorescein glucuronide, a metabolite of fluorescein, also fluoresces. To assess the influence of fluorescein glucuronide on the quantitation of fluorescein by fluorescence, we studied the pharmacokinetics of fluorescein and fluorescein glucuronide for 38 hr in the plasma of five normal subjects given 14 mg/kg of sodium fluorescein intravenously. The plasma and the plasma ultrafiltrate were measured by fluorescence and by high performance liquid chromatography. In our fluorophotometer, fluorescein glucuronide was 0.124 times as fluorescent as fluorescein. Fluorescein was rapidly converted to fluorescein glucuronide, and within 10 min the concentration of unbound fluorescein glucuronide exceeded that of unbound fluorescein. The terminal half-lives of fluorescein and fluorescein glucuronide in the plasma ultrafiltrate were 23.5 and 264 min, respectively, so that fluorescein glucuronide contributed almost all of the plasma fluorescence after 4-5 hr. Because fluorescein glucuronide was less bound in the plasma than fluorescein, the ratio of the fluorescence of the plasma ultrafiltrate to that of the plasma increased with time. The greatest proportion of the total fluorescein available to penetrate into the ocular compartments occurred shortly after injection. ... [Blair NP et al; Invest Ophthalmol Vis Sci 27 (7): 1107-14 (1986). Available from, as of October 20, 2009:] PubMed Abstract

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