Basic information
- CAS
3326-32-7- Standard SMILES
O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21- InChIKey
MHMNJMPURVTYEJ-UHFFFAOYSA-N- Molecular formula
- C21H11NO5S
- Average molar mass
- 389.4 g/mol
- Monoisotopic mass
- 389.03579362
Names & identifiers
- Preferred name
- Fluorescein 5-isothiocyanate
- IUPAC
- 3',6'-dihydroxy-6-isothiocyanatospiro[2-benzofuran-3,9'-xanthene]-1-one
- English name
- Fluorescein 5-isothiocyanate
- Molecular formula
- C21H11NO5S
- Molecular weight
- 389.38
Names & synonyms
Show more names
Database identifiers
- CAS
3326-32-7- PubChem CID
- 18730
- DTXSID
DTXSID80892440- ChEMBL
CHEMBL516313- ChEBI
CHEBI:37918- UNII
- I223NX31W9
- EC Number
- 222-042-0
- Nikkaji
- J205.408F
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 120 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 668
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 360 °C · >360 °C(lit.)
- Boiling point
- 708.6 · 708.6±60.0 °C(Predicted)
- Density
- 1.3423 · 1.3423 (rough estimate)
- refractive index
- 1.506 · 1.5060 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Slightly soluble in DMSO, ethanol, methanol DMF and acetone
- form
- powder
- pka
- 2.2 · 2.2, 4.4, 6.7(at 25℃)
- color
- White
- PH Range
- Weak green uorescence (6.0) to strong green uorescence (7.2)
- Appearance
- Yellow solid
- Water Solubility
- practically insoluble
- Sensitive
- Moisture Sensitive
- λmax
- 490 nm · 490nm
- ex/em
- 492 · 492/520 nm (PBS buffer)
- ε(extinction coefficient)
- 74 · 74,000 L⋅mol−1⋅cm−1
- Φ(quantum yield)
- 0.92 · 0.92
- BRN
- 1407295 · 1407295
- Stability
- Stability Stable, but moisture-sensitive. Incompatible with strong oxidizing agents, strong bases, amines, acids.
- Major Application
- Magnetic nanowires, immunoassays, analyzing proteins, identifying chromosomes, Salmonella mosomes, diagnosis of cancer, kidney diseases, detecting pathogens, genes, Salmonella cells, toxoplasmosis, enzyme-mediated nucleic acid cleavage, surface molecules on colorectal cancers, treating cancer, chronic lymphocytic leukemia
- Biological Applications
- 16 diagnosing · Analyzing sugar chain; detecting iodide/iodate or total iodine; detecting/imaging thiols; detecting/quantifying biotin derivatives;16 diagnosing classical Hodgkin lymphoma (CHL) in lymph nodes; cellulose nanocrystals for bioimaging applications; treating neuroinflammation; treating/diagnosing cancer; PEO-PCL-PEO triblock copolymers for topical delivery; polymersomes in biomedical or cosmetic applications;apoptosis assay; as a substrate for measuring heparanase activity, human immunodeficiency virus (HIV-1) proteinase activity, kinase activity, phosphatase activity, β-lactamase activity, transglutaminase (TG2) activity; implantable drug-delivery devicess
- InChI
- 1S/C21H11NO5S/c23-12-2-5-16-18(8-12)26-19-9-13(24)3-6-17(19)21(16)15-4-1-11(22-10-28)7-14(15)20(25)27-21/h1-9,23-24H
- InChIKey
- MHMNJMPURVTYEJ-UHFFFAOYSA-N
- SMILES
- Oc1ccc2c(Oc3cc(O)ccc3C24OC(=O)c5cc(ccc45)N=C=S)c1
- CAS DataBase Reference
- 3326 · 3326-32-7(CAS DataBase Reference)
- FDA UNII
- 223 NX31W9 · I223NX31W9
- EPA Substance Registry System
- -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato- (3326-32-7)
- UNSPSC Code
- 41116133 · 41116133
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P272-P280-P284-P302+P352-P333+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 42 · 42/43-36/37/38-22
- Safety Statements
- 22 · 22-45-36/37/39-26-36/37-36
- WGK Germany
- 3 · 3
- F
- 10 · 10
- TSCA
- TSCA listed
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Resp. Sens. 1Skin Sens. 1
Safety & regulation
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin];H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 169 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;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.
Hazard information
Regulatory Information
Chemical: Spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Toxicity Summary
Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Regulatory information
Regulatory Information
Chemical: Spiro[isobenzofuran-1(3H),9'-(9H)xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329990
- risk_code
- 42/43-36/37/38-22
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn,Xi
- safety_code
- 22-45-36/37/39-26-36/37-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P284-P302+P352-P333+P313
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
MeSH Pharmacological Classification
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.
Uses & manufacturing
Uses
Used as a fluorescent indicator to probe biological systems and monitor sewage; [Merck Index]
Fluorescein isothiocyanate is used in flow cytometry. (L552)
Applications
DescriptionFluorescein 5-isothiocyanate (5-FITC) is an isomer of fluorescein isothiocyanate (FITC), which is commonly used as a mixture of the 5- and 6-isothiocyanate isomers. It reacts with amine and thiol groups to form conjugates with proteins, lipids, and other molecules for detection by a variety of fluorescent-based applications. 5-FITC displays excitation/emission maxima of 494/519 nm, respectively.
UsesFluorescein isothiocyanate isomer I has been used for the staining of conidia. It is a kind of fluorescent marker for biochemical applications. Reacts under mild conditions with primary amines and it is also used in modification of actin at lys-61, labelling of FAB and the modification of thiol groups.
General DescriptionFluorescein isothiocyanate (FITC) is yellow-orange in color with an absorption maximum at 495nm. Upon excitation, it emits a yellow-green color with an emission maximum at 525nm.It is widely used to attach a fluorescent label to proteins via the amine group. The isothiocyanate group reacts with amino terminal and primary amines in proteins. It has been used for the labeling of proteins including antibodies and lectins.Fluorescein isothiocyanate isomer I has been proposed as a contact sensitizer.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: Fluorescein 5-isothiocyanate is the 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.
Related reactions
Compound notes
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