Grundinformationen
- Standard-SMILES
O=C1OC2(c3ccc(O)cc3Oc3cc(O)ccc32)c2ccc(N=C=S)cc21- InChIKey
MHMNJMPURVTYEJ-UHFFFAOYSA-N- Summenformel
- C21H11NO5S
- Durchschnittliche Molmasse
- 389,4 g/mol
- Monoisotopische Masse
- 389,03579362
Namen und Bezeichner
- Bevorzugter Name
- Fluorescein 5-isothiocyanate
- IUPAC
- 3',6'-dihydroxy-6-isothiocyanatospiro[2-benzofuran-3,9'-xanthene]-1-one
- Lokaler Name
- 2-(6-Hydroxy-3-oxo-(3H)-xanthen-9-yl)-5-isothiocyanatobenzoesure
- Englischer Name
- Fluorescein 5-isothiocyanate
- Summenformel
- C21H11NO5S
- Molmasse
- 389.38
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
3326-32-7- PubChem CID
- 18730
- DTXSID
DTXSID80892440- ChEMBL
CHEMBL516313- ChEBI
CHEBI:37918- UNII
- I223NX31W9
- EC Number
- 222-042-0
- Nikkaji
- J205.408F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 120 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 668
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 360 °C · >360 °C(lit.)
- Siedepunkt
- 708.6 · 708.6±60.0 °C(Predicted)
- Dichte
- 1.3423 · 1.3423 (rough estimate)
- Brechungsindex
- 1.506 · 1.5060 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Slightly soluble in DMSO, ethanol, methanol DMF and acetone
- Aggregatzustand
- powder
- pka
- 2.2 · 2.2, 4.4, 6.7(at 25℃)
- Farbe
- White
- Wasserlöslichkeit
- practically insoluble
- BRN
- 1407295 · 1407295
- Stabilität
- 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
- 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 Datenbank
- 3326 · 3326-32-7(CAS DataBase Reference)
- EPA chemische Informationen
- -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato- (3326-32-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
Toxikologische Informationen
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)
Regulatorische Informationen
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
Sicherheitsdaten
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329990
- risk_code
- 42/43-36/37/38-22
- hazard_code
- Xn,Xi
- safety_code
- 22-45-36/37/39-26-36/37-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
Uses
Used as a fluorescent indicator to probe biological systems and monitor sewage; [Merck Index]
Fluorescein isothiocyanate is used in flow cytometry. (L552)
Anwendungen
BeschreibungFluorescein 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…