Sodium Fluorescein

HCID 10608CAS 518-47-8

基本情報

標準SMILES
O=C([O-])c1ccccc1-c1c2ccc(=O)cc-2oc2cc([O-])ccc12.[Na+].[Na+]
InChIKey
NJDNXYGOVLYJHP-UHFFFAOYSA-L
分子式
C20H10Na2O5
平均分子量
376.3 g/mol

概要

Fluorescein, disodium salt is an orange-red to dark red powder. Water-soluble form of fluorescein. Odorless and almost tasteless. pH (5% solution) 7.8. May be sensitive to prolonged exposure to light and to heat.

名称と識別子

優先名称
Sodium Fluorescein
IUPAC
disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate

名称と別名

Fluorescein disodium saltSoluble fluoresceinSodium fluoresceinUraninUranine WSSResorcinol phthalein sodiumUranine YellowAk-FluorFluorescein, solubleKi202Sodium fluoresceinateFluoresceinum natricum
名称をさらに表示
93X55PE38XD&C Yellow No. 8Funduscein-25Ki202(1)Ki202(2)D & C Yellow no. 8disodium 2-(6-oxido-3-oxo-3H-xanthen-9-yl)benzoateCI 45350

データベース識別子

CAS
518-47-8
PubChem CID
10608
ChEMBL
CHEMBL1628233
UNII
93X55PE38X
EC Number
208-253-0
Nikkaji
J79.264K

物性

構造計算による物性

極性表面積
89.5 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
1
重原子数
27

実験および物理化学的性質

Chemical ClassesDyes -> Other Dyes
CosmeticsHair dyeing; Cosmetic colorant
Food AdditivesDrugs, Cosmetics, Devices -> FDA Regulatory Status of Color Additives
Density1.601 (NTP, 1992) - Denser than water; will sink
Color/Form · 3 件

Orange-red powder

Yellow powder

Orange-brown powder

Solubility · 4 件

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

Soluble in ethanol, glycerol, dilute acetone

Slightly soluble in alcohol

In water, 4.0X10+4 mg/L, temperature not specified

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 87.1% (263 of 302) of all reports.

Warning

H315 (10.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 302 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-, disodium salt

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-, sodium salt (1:2) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-, sodium salt (1:2) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17278

C.I. Acid Yellow 73: Non hazardous

Other Safety InformationIMAP assessments - Fluorescein and its sodium salt: Human health tier II assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Fire PotentialThis material is assumed to be combustible.
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this compound include irritation of the eyes. It may also cause irritation of the skin. Excess inhalation of the dust can cause the onset of asthma. Other symptoms include nausea, urticaria, sneezing, bitter taste and dizziness. There is a low incidence of serious side effects including respiratory embarrassment, pulmonary edema, pharyngeal edema, cardiac arrest, myocardial infarction, shock, hypotension and death. Symptoms that may occur after intravenous injection include vomiting, syncope and urticaria. The skin and urine may be transiently colored.

Hazards SummaryCauses changes in motor activity, ataxia, and dyspnea in oral lethal-dose studies of mice and rats; [RTECS] A skin, eye, and respiratory tract irritant; [HSDB] May cause irritation; Targets the kidney; [Sigma-Aldrich MSDS] See Fluorescein.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 1 件

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.

Storage ConditionsStore at 2 deg - 25 °C (36 deg - 77 °F). Do Not Freeze
Cleanup MethodsWipe 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.
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

毒性情報

Ecotoxicity Values · 4 件

LC50; Species: Daphnia pulex (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 25 °C, pH 7.4-7.8, hardness 80-100 mg/L CaCO3, alkalinity 60-70 mg/L CaCO3, conductivity 260-320 umhos/cm, dissolved oxygen >8.0 mg/L; Concentration: 337000 ug/L for 48 hr (95% confidence interval: 278000-403000 ug/L) /formulation/

LC50; Species: Oryzias latipes (Medaka); Conditions: freshwater, static, 25 °C; Concentration: 3000000 ug/L for 48 hr

LC50; Species: Psetta maxima (Left-Eyed Flounder) length 4 cm, weight 1.5 g; Conditions: saltwater, static, 14.0 °C, pH 8.1, salinity 36.0'%, dissolved oxygen 7.9 mg/L; Concentration: 997100 ug/L for 24 hr

LC50; Species: Psetta maxima (Left-Eyed Flounder) length 4 cm, weight 1.5 g; Conditions: saltwater, static, 14.0 °C, pH 8.1, salinity 36.0'%, dissolved oxygen 7.9 mg/L; Concentration: 997100 ug/L for 96 hr

Environmental Fate · 5 件

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 88.81 in a silty clay soil and 69.43 in a sediment(2), indicate that D&C Yellow No. 8 is expected to have high mobility in soil(SRC). Volatilization of D&C Yellow No. 8 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). D&C Yellow No. 8 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-17 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). D&C Yellow No. 8, present at 100 mg/L, exhibited <25% elimination in 42 days using an activated sludge inoculum at 0.5 mg/L dry material in the modified static test suggesting the dye may be resistant to biodegradation(4).

TERRESTRIAL FATE: A field study was conducted to identify critical parameters governing the mobility and fate of pesticides in soil/aquifer systems. The test field as located in Juelich, Krauthausen, Germany, characterized as a loamy 20-20% clay; the underlying aquifer consists of fluvial sands and gravel. Only 0.18% of the injected uranine mass could be recovered after 365 days. A mean plume velocity of 0.089 m/day was calculated(1).

AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 88.81 in a silty clay soil and 69.43 in a sediment(2), indicate that D&C Yellow No. 8 is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.8X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 75(SRC), from an estimated log Kow of -0.67(4) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). D&C Yellow No. 8, present at 100 mg/L, exhibited <25% elimination in 42 days using an activated sludge inoculum at 0.5 mg/L dry material in the modified static test suggesting the dye may be resistant to biodegradation(6).

AQUATIC FATE: Sure-Dye formulation was accidentally spilled on the staging area of the Kaiku agricultural landing strip on Kauai Island, HI, October 18, 1996. The formulation was comprised of phloxine B and uranine; spill amounts of 1.2 and 0.54 kg, respectively. The concentration of uranine in a puddle immediately following the spill was approximately 500 ppm; levels decreased to 3 ppb 26 days after the spill. None was detected in the Halenanahu Reservoir, 100 feet away. No uranine was detected in sediment samples from the puddle(1). /Uranine/

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), D&C Yellow No. 8, which has an estimated vapor pressure of 1.6X10-17 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase D&C Yellow No. 8 may be removed from the air by wet or dry deposition(SRC). D&C Yellow No. 8 absorbs light at wavelengths of 493 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Milk ConcentrationsFluorescein sodium has been demonstrated to be excreted in human milk.
Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ The toxicity of two xanthene dyes, fluorescein sodium salt and phloxine B, to Daphnia pulex was assessed using acute and chronic level toxicological endpoints. The 48-hr LC50 (95% FL) of fluorescein and phloxine B to D. pulex neonates was 337 (278-403) mg/L and 0.423 (0.376-0.477) mg/L, respectively. Statistical comparison of the lethal concentration regressions showed no significant difference between the slopes of the two curves. Acute exposure to combinations of these two dyes together resulted in a synergistic increase in mortality compared to exposure to each dye separately. Following 10-day chronic exposure under static conditions, fluorescein caused a concentration-dependent decline in the mean number of offspring produced by D. pulex. In contrast, chronic exposure to phloxine B did not appear to result in significant sublethal effects with respect to the reproductive potential of exposed organisms.

Effluent ConcentrationsUranine was detected, not quantified in unspecified Japanese sewage plant effluent which received dye industry wastewater(1). /Uranine/
Soil Adsorption/Mobility · 1 件

A Koc of 88.81 in Lihue silty clay (pH 7.0; 18.6 % iron; 7640 ug/g Ca; 1632 ug/g Mg; 3.10% organic carbon) was been reported for uranine(1). According to a classification scheme(2), this Koc value suggests that uranine is expected to have high mobility in soil. The octanol-isotonic salt solution partition coefficient is 0.72 at 25 °C. Sorption experiments indicate that uranine tends to stay in the aqueous phase at low concentration. A Koc of 69.43 has been measured in sediment (pH 8.0; 18.7 % iron; 2398 ug/g Ca; 109 ug/g Mg; 3.94% organic carbon)(1). Freundlich sorption coefficients in Rur gravel and Rhine gravel of 0.76 and 0.42, respectively, have been reported using a uranine concentration in the range of 2-500 ug/L(3). /Uranine/

法規制情報

FDA Requirements · 4 件

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.

All batches of this color additive when used as a color additive for externally applied drugs shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.

All batches of this color additive when used as a color additive in externally applied cosmetics shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.

A batch of this straight color may be certified, in accordance with 21 CFR Part 82, for use in externally applied drugs and cosmetics, if such batch conforms to the requirements of 21 CFR 82.5 and to the specifications in 21 CFR Part 82.

化学と産業

薬理情報

Mechanism of Action · 1 件

Fluorescein sodium responds to electromagnetic radiation and light between the wavelengths of 465 to 490 nm and fluoresces, i.e., emits light at wavelengths of 520 to 530 nm. Thus, the hydrocarbon is excited by blue light and emits light that appears yellowish green. Following intravenous injection of fluorescein sodium in an aqueous solution, the unbound fraction of the fluorescein can be excited with a blue light flash from a fundus camera as it circulates through the ocular vasculature, and the yellowish green fluorescence of the dye is captured by the camera. In the fundus, the fluorescence of the dye demarcates the retinal and/or choroidal vasculature under observation, distinguishing it from adjacent areas/structures.

Biological Half-Life · 1 件

... The pharmacokinetics of fluorescein and fluorescein glucuronide /were studied/ for 38 hr in the plasma of five normal subjects given 14 mg/kg of sodium fluorescein intravenously. ... The terminal half-lives of fluorescein and fluorescein glucuronide in the plasma ultrafiltrate were 23.5 and 264 min, respectively, ... .

Metabolism/Metabolites · 1 件

Fluorescein is metabolized to fluorescein monoglucuronide. After IV administration of fluorescein sodium (14 mg/kg) to 7 healthy subjects, approximately 80% of fluorescein in plasma was converted to glucuronide conjugate after a period of 1 hour post dose.

FDA Pharmacological Classification · 2 件

FLUORESCEIN SODIUM

Dyes [MoA]; Diagnostic Dye [EPC]

MeSH Pharmacological Classification · 2 件

Substances used to allow enhanced visualization of tissues.

Chemicals 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.

Absorption, Distribution and Excretion · 5 件

Uranine is rapidly absorbed in the lungs and in the respiratory tract, and is affected by the presence of surfactants. It is not metabolized in the lung. Inhaled uranine is excreted in the urine.

Within 7 to 14 seconds after IV administration into the antecubital vein, fluorescein usually appears in the central retinal 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 6 to 12 hours after dosing. Various estimates of volume of distribution indicate that fluorescein distributes into interstitial space (0.5 L/kg).

Fluorescein sodium has been demonstrated to be excreted in human milk.

Fluorescein and its metabolite 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.

For more Absorption, Distribution and Excretion (Complete) data for D&C Yellow No. 8 (7 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used in analysis of subterranean waters, as a reagent (protein label, immunohistological stain, and immunofluorescent label), diagnostic aid (corneal abrasions), and for ophthalmic angiography and contact lens fitting; [Merck Index] Used as a marker for sea rescues, for dyeing silk and wool, to make fluorescent laminates, and in commercial antifreezes; [HSDB] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Highly purified product is used in solution as a diagnostic aid for evaluating corneal trauma and for treating intraocular inflammation.

Because of its intense fluorescence and /non-/biodegradability, it is in great demand for tracing the course of underground streams and of factory effluents and sewage sources that contaminate underground water supplies.

As a marker for sea-rescue operations

Dyeing silk and wool yellow

U.S. Production · 2 件

2023: 35,700 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7954]

Consumer UsesNot Known or Reasonably Ascertainable
Methods of ManufacturingBy treatment of fluorescein with sodium carbonate solution and crystallizing.
Formulations/Preparations · 4 件

Grades: Technical, USP (as sodium fluorescein)

Trade names: C.I. Acid Yellow 73; Fluor-I-strip A.T.; Ful-Glo; 12417 Yellow; 11824 Yellow

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

Household ProductsInformation on 19 consumer products that contain D&C Yellow #8 (C.I. 45350) in the following categories is provided:

関連反応

2 件

関連ノート

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