| Identification | More | [Name]
Fluorescein | [CAS]
2321-07-5 | [Synonyms]
ACID YELLOW 73
CI 45350
CI 45350.1
CI 45350:1
CI NO 45350
D AND C YELLOW NO 7
FLUORESCEIN
FLUORESCEIN, ALCOHOL SOLUBLE
RESORCINOL PHTHALEIN
S NO 880
SOLVENT YELLOW 94
11712yellow
2-(6-hydroxy-3-oxo-3h-xanthen-9-yl)-benzoicaci
3,6-dihydroxyspiro(xanthene-9,3’-phthalide)
3,6-fluorandiol
3’,4’-dehydroxyfluoran
3’,6’-dihydroxy-fluora
3’,6’-dihydroxyfluoran
3’,6’-dihydroxyspiro(isobenzofuran-1(3h),9’(9h)-xanthen)-3-one
3’,6’-fluorandiol | [EINECS(EC#)]
219-031-8 | [Molecular Formula]
C20H12O5 | [MDL Number]
MFCD00005050 | [Molecular Weight]
332.31 | [MOL File]
2321-07-5.mol |
| Chemical Properties | Back Directory | [Appearance]
orange-red crystalline powder | [Melting point ]
320 °C(lit.)
| [Boiling point ]
429.44°C (rough estimate) | [density ]
1.2739 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Solubility Insoluble in water, ether, benzene, chloroform; soluble in ethanol, methanol, acetone, Iethyl acetate, N,N-dimethylformamide | [Colour Index ]
45350 | [form ]
Powder | [pka]
2.2, 4.4, 6.7(at 25℃) | [color ]
Red to orange | [PH Range]
Pink uorescence (4.0) to green uorescence (6.0) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
insoluble | [λmax]
493.5nm, 496nm, 460nm, 515nm | [Merck ]
14,4159 | [BRN ]
94324 | [Biological Applications]
Detecting
chromosomal aberration; diagnosing corneal
diseases; marking/detecting insects; as antitumor
agent; as antihistaminic agent; use in agriculture
and plant cultivation; use in cosmetics; use in
ophthalmology; as a substrate for measuring
α-amylases activity, elastases activity, esterases
activity, β-glucuronidases activity, horseradish
peroxidases activity, kinases activity, monoamine
oxidases (MAOs) activity, phosphatases activity,
phospholipases activity, proteases/proteinases
activity, telomerases activity activity | [Major Application]
Organic light-emitting diode, nanoparticles, liquid crystal display, oil products, lip make-up, nucleic acid synthesis, amplification, sequencing and cloning, diagnosis of diabetic retinopathy, detecting yeast, multidrug resistance, proteins, antiHCV antibodies, target genes, enzymatic activity, nerve agent, nucleic acid sequences, imaging lung cancer, prostate cancer | [LogP]
2.980 (est) | [CAS DataBase Reference]
2321-07-5(CAS DataBase Reference) | [EPA Substance Registry System]
2321-07-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R43:May cause sensitization by skin contact.
R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 ]
3
| [RTECS ]
LM5075000
| [F ]
10-21 | [TSCA ]
Yes | [HS Code ]
32042000 | [Safety Profile]
Poison by intravenous
route. Moderately toxic by intraperitoneal
route. Mutation data reported. When heated
to decomposition it emits acrid smoke and
irritating fumes. See also FLUORESCEIN SODIUM. | [Hazardous Substances Data]
2321-07-5(Hazardous Substances Data) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Phthalic anhydride-->Resorcinol-->Resorcinol-->Phthalic anhydride | [Preparation Products]
ERYTHROSIN B-->Fluorescein isothiocyanate-->2',7'-dibromo-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthene]-3-one-->FLUORESCEIN CHLORIDE-->3',6'-DIMETHOXYFLUORAN-->EOSIN B-->4'-Bromo-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one-->3',6'-Bis{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy]-3H-[spiro(isobenzofuran-1,9,-xanthen]-3-one} FBBBE-->FLUORESCEIN DIBUTYRATE-->2-(3,7-DIHYDROXY-DIBENZO[B,F][1,4]OXAZEPIN-11-YL)-BENZOIC ACID-->DIIODOFLUORESCEIN |
| Hazard Information | Back Directory | [General Description]
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. | [Reactivity Profile]
FLUORESCEIN(2321-07-5) is incompatible with strong oxidizers. Also incompatible with acids, acid salts and salts of heavy metals. . | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this material is not available, but FLUORESCEIN is probably combustible. | [Description]
Fluorescein is a synthetic organic compound available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used as a fluorescent tracer for many applications.
Fluorescein is a fluorophore commonly used in microscopy, in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains, and in dye tracing. Fluorescein has an absorption maximum at 494 nm and emission maximum of 521 nm (in water). The major derivatives are fluorescein isothiocyanate (FITC) and, in oligonucleotide synthesis, 6-FAM phosphoramidite.
Fluorescein also has an isosbestic point (equal absorption for all pH values) at 460 nm. Fluorescein is also known as a color additive (D&C Yellow no. 7). The disodium salt form of fluorescein is known as uranine or D&C Yellow no. 8.
The color of its aqueous solution varies from green to orange as a function of the way it is observed: by reflection or by transmission, as it can be noticed in bubble levels in which fluorescein is added as a colorant to the alcohol filling the tube to increase the visibility of the air bubble and the precision of the instrument. More concentrated solutions of fluorescein can even appear red. | [Chemical Properties]
Orange-red, crystalline powder. Very
dilute alkaline solutions exhibit intense greenishyellow fluorescence by reflected light, while the
solution is reddish-orange by transmitted light.soluble in dilute alkalies, boiling alcohol, ether, dilute acids, and | [Physical properties]
The fluorescence of this molecule is very intense; peak excitation occurs at 494 nm and peak emission at 521 nm.
Fluorescein has a pKa of 6.4, and its ionization equilibrium leads to pH-dependent absorption and emission over the range of 5 to 9. Also, the fluorescence lifetimes of the protonated and deprotonated forms of fluorescein are approximately 3 and 4 ns, which allows for pH determination from non intensity based measurements. The lifetimes can be recovered using time-correlated single photon counting or phase-modulation fluorimetry. | [Uses]
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 to target the fluorophore to specific proteins or structures within cells | [Uses]
corneal trama indicator | [Application]
Biochemical research
In cellular biology, the isothiocyanate derivative of fluorescein is often used to label and track cells in fluorescence microscopy applications (for example, flow cytometry). Additional biologically active molecules (such as antibodies) may also be attached to fluorescein, allowing biologists to target the fluorophore to specific proteins or structures within cells. This application is common in yeast display.
Health care applications
"Fluorescein sodium", the sodium salt of fluorescein, is used extensively as a diagnostic tool in the field of ophthalmology and optometry, where topical fluorescein is used in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It is also used in rigid gas permeable contact lens fitting to evaluate the tear layer under the lens.
Uses in river systems
In 1966, environmentalists forced a change to a vegetable-based dye to protect local wildlife. Other uses of fluorescein include using it as a water-soluble dye added to rainwater in environmental testing simulations to aid in locating and analyzing any water leaks, and in Australia and New Zealand as a methylated spirit dye.
Oil field application
Fluorescein dye solutions, typically 15 % active, are commonly used as an aid to leak detection during hydrostatic testing of sub sea oil and gas pipelines and other subsea infrastructure. Leaks can be detected by divers carrying ultraviolet lights. | [Definition]
A fluorescent
dye used as an absorption indicator. | [Definition]
ChEBI: A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy. | [Safety]
Topical, oral, and intravenous use of fluorescein can cause adverse reactions, including nausea, vomiting, hives, acute hypotension, anaphylaxis and related anaphylactoid reaction, causing cardiac arrest and sudden death due to anaphylactic shock.
The most common adverse reaction is nausea, due to a difference in the pH from the body and the pH of the sodium fluorescein dye; a number of other factors , however, are considered contributors as well. The nausea usually is transient and subsides quickly. Hives can range from a minor annoyance to severe, and a single dose of antihistamine may give complete relief. Anaphylactic shock and subsequent cardiac arrest and sudden death are very rare, but because they occur within minutes, a health care provider who uses fluorescein should be prepared to perform emergency resuscitation. | [Synthesis]
Fluorescein was first synthesized by Adolf von Baeyer in 1871. It can be prepared from phthalic anhydride and resorcinol in the presence of zinc chloride via the Friedel - Crafts reaction.
A second method to prepare fluorescein uses methanesulfonic acid as a Br?nsted acid catalyst. This route has a high yield under milder conditions. | [Derivatives]
There are many fluorescein derivatives. For example, fluorescein isothiocyanate 1, often abbreviated as FITC, is the original fluorescein molecule functionalized with an isothiocyanate group ( - N = C = S ) , replacing a hydrogen atom on the bottom ring of the structure. This derivative is reactive towards primary amine groups of biologically relevant compounds including intracellular proteins to form a thiourea linkage. A succinimidyl ester functional group attached to the fluorescein core, creating NHS-fluorescein, forms another common amine-reactive derivative, yielding more stable amide adducts. Penta fluoro phenyl esters (PFP) and tetra fluoro phenyl esters (TFP) are other useful reagents. In oligonucleotide synthesis, several phosphoramidite reagents containing protected fluorescein, e.g. 6-FAM phosphoramidite 2, are widely used for the preparation of fluorescein-labeled oligonucleotides.
Other green dyes include Oregon Green, Tokyo Green, SNAFL, and carboxy naphtho fluorescein. These dyes, along with newer fluoro phores such as Alexa 488, Fluo Probes 488 and DyLight 488, have been tailored for various chemical and biological applications where higher photo stability, different spectral characteristics, or different attachment groups are needed. |
|
|