플루오레세인

3.4

3.4

Red, orthorhombic prisms

Yellowish-red to red powder

Orange-red, crystalline powder

Insoluble (NTP, 1992)

600

Slightly soluble in ethanol, diethyl ether; very soluble in acetone; soluble in pyridine, methanol

Insoluble in benzene, chloroform, ether. Soluble in hot alcohol or glacial acetic acid; also soluble in alkali hydroxides or carbonates with a bright green fluorescence appearing red by transmitted light.

In water, 50 mg/L at 20 °C

2.55e-02 g/L

Decomposes at 554 °F. In sealed tube, melts at 597-601 °F with decomposition (NTP, 1992)

315

315 °C (decomposes)

315 °C

Fluorescein appears as yellow amorphous solid or orange-red crystals. Latter have greenish-yellow fluorescence by reflected light. Insoluble in water. Soluble in dilute aqueous bases. Very dilute alkaline solutions exhibit intense, greenish-yellow fluorescence by reflected light. Low toxicity. May be sensitive to prolonged exposure to light.

Yellowish-red to red solid; [Merck Index] Orange powder; [MSDSonline]

Solid

176.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0038887]；174.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0038887]；176.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9025328]；190.6 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0038887]；189.1 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9025328]；174.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9025328]；173.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9025328]；174.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID0038887]

172.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

170.75 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；189.36 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；162.47 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

This chemical does not meet GHS hazard criteria for 3.4% (13 of 383) of reports.

Warning

H302 (13.6%): Harmful if swallowed [Warning Acute toxicity, oral]；H319 (96.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 383 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 13 of 383 reports by companies.；There are 5 notifications provided by 370 of 383 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

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

Status: Active Update: 13-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20362

Fluorescein: Does not have an individual approval but may be used under an appropriate group standard

This material is assumed to be combustible.

Slight.

Has caused adverse reactions by IV injection including cardiac arrest, severe shock, and anaphylaxis; In 547 patients, about 10% had adverse responses with nausea frequent, vomiting infrequent, and urticaria rare; [HSDB] A positive prick skin test was reported in one patient; [eChemPortal: ERMA] An irritant; [MSDSonline]

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.

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.；SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.；INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

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.

SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.；STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

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.

20 [mg/m3]

220 [mg/m3]

1300 [mg/m3]

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Wear approved respiratory protection, chemically compatible gloves and protective clothing.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.6X10+5(SRC), determined from a structure estimation method(2), indicates that fluorescein is expected to be immobile in soil(SRC). Volatilization of fluorescein from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Fluorescein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.6X10+5(SRC), determined from a structure estimation method(2), indicates that fluorescein is 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 8.9X10-17 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 3.35(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data in water were not available(SRC, 2011).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluorescein, which has an estimated vapor pressure of 4.0X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase fluorescein may be removed from the air by wet or dry deposition(SRC). fluorescein contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Common: paresthesia of lips, change in taste (orally), severe eye-stinging and irritation (ophthalmic), severe nausea, vomiting, abdominal pain, chest pain, and extravasation.；* Mild: urine discoloration, skin inflammation/discoloration at the injection site；* Moderate: rashes, urticaria, syncope/dizziness/hypotension, angioedema, chest pain；* Severe: nerve palsy, seizure, bronchospasm, pulmonary edema, epithelial keratopathy, anaphylaxis；Corneal opacification can occur with prolonged use.

Fluorescein toxicity is low. Proper doses of epinephrine and antihistamines can manage cases of significant hypersensitivity after flushing the affected area with plenty of water. Prevention of anaphylaxis is possible by providing a minimal dose of fluorescein to determine if a minor reaction would occur.；If enough fluorescein is issued intravenously, precaution is necessary for nursing mothers because another route of excretion is through human milk, causing it to turn yellow.

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.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of fluorescein can be estimated to be 2.6X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that fluorescein is expected to be immobile mobility in soil.

/SIGNS AND SYMPTOMS/ Possible allergic reaction to material if inhaled, ingested or in contact with skin.

/SIGNS AND SYMPTOMS/ Males react adversely more frequently than females to iv fluorescein angiography. In 547 pt, 12.8% of males & 7.3% of females had adverse responses. Nausea was most common, vomiting infrequent, and urticaria rare.

/OTHER TOXICITY INFORMATION/ Fluorescein admin iv has been very widely used in pt without evident toxicity to eye.

Fluorescein's production and use as a silk and wool dye, indicator and reagent for bromine(1) and in eye surgery(2) may result in its release to the environment through various waste streams(SRC). Its use for surface water for spotting purposes and as a tracer to locate impurities in wells(1) will result in its direct release to the environment(SRC).

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

fluorescein

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

An estimated BCF of 75 was calculated in fish for fluorescein(SRC), using an estimated log Kow of 3.35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Henry's Law constant for fluorescein is estimated as 8.9X10-17 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that fluorescein is expected to be essentially nonvolatile from water and moist soil surfaces(2). Fluorescein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-14 mm Hg(SRC), determined from a fragment constant method(3).

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

Status: Active Update: 13-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20362

Fluorescein: Does not have an individual approval but may be used under an appropriate group standard

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.

S01JA01

S - Sensory organs；S01 - Ophthalmologicals；S01J - Diagnostic agents；S01JA - Colouring agents；S01JA01 - Fluorescein

QS - Sensory organs；QS01 - Ophthalmologicals；QS01J - Diagnostic agents；QS01JA - Colouring agents；QS01JA01 - Fluorescein

S01JA01

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.

Fluorescein sodium responds to electromagnetic radiation and light between the wavelengths of 465-490 nm and fluoresces, i.e., emits light at wavelengths of 520-530 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. /Fluorescein sodium/

... 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, ... .

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. ...

Fluorescein undergoes rapid metabolism 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, indicating relatively rapid conjugation.

Fluorescein is a known human metabolite of zinc15020070.

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

TPY09G7XIR

FLUORESCEIN

Established Pharmacologic Class [EPC] - Diagnostic Dye

Mechanisms of Action [MoA] - Dyes

Fluorescein is a Diagnostic Dye. The mechanism of action of fluorescein is as a Dye.

FLUORESCEIN

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.

Rapidly distributed

Fluorescein and its metabolites are mainly eliminated via renal excretion.

0.5 L/kg

renal cl=1.75 mL/min/kg [After IV administration]；hepatic cl=1.50 mL/min/kg [After IV administration]

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).

Used as dye for cosmetics, cleansers, other household products, and vascular and ophthalmic diagnosis (may be in form of sodium salt); Used as water indicator (detect leaks, pollution sources, and for sea rescues), adsorption indicator, and dye intermediate; [HSDB] Used as analytical and clinical reagent; [Merck Index]

A presumptive reagent for dilute blood detection other than luminol is fluorescein.

Yellow dye for cosmetics, cleansers, and other household products; tracing agent for water leaks; dye to detect water pollution sources; adsorption indicator; stic agent in ophthalmology (sodium salt); chem int for dyes

As a marker for life saving at sea ... /and/ detecting water leaks.

Dyeing seawater for spotting purposes, tracer to locate impurities in wells, dyeing silk and wool, indicator and reagent for bromine.

For more Uses (Complete) data for FLUORESCEIN (7 total), please visit the HSDB record page.

2-(2-4,dihydroxybenzoyl)benzoic acid

Phthalic acid

Resorcinol

(1986) No Data

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3868]；[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'-

Condensation of resorcinol with phthalic anhydride in the presence of zinc chloride

By heating phthalic anhydride and resorcinol.

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

Its diagnostic usefulness rests upon its fluorescence ... Appears readily in extracellular fluid and gains access only to viable cells ... Ulcerated areas ... stained green, foreign bodies ... surrounded by green ring, and loss of substance in conjunctiva ... indicated by yellow stain.

Color additives were initially regulated in the United States under the U.S. Department of Agriculture's (USDA) Bureau of Chemistry. In 1906, the Food and Drugs Act was passed by Congress, which prohibited the use of poisonous or deleterious colors in confectionery and the coloring or staining of food to conceal damage or inferiority. In 1927, responsibility of the Food and Drugs Act was transferred to FDA. Increasing government oversight, the Federal Food, Drug, and Cosmetic Act (FFDCA) was passed in 1938 and established the three following categories for colors: FD&C: colors used in foods, drugs and cosmetics; D&C: colors used in drugs and cosmetics when in contact with mucous membranes or ingested; and Ext. D&C: colors used in products applied externally.