Fluorescein 5-isothiocyanate

HCID 18730

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

3326-32-75-FITCFLUORESCEIN-5-ISOTHIOCYANATEfluorescein 5-isothiocyanate5-isothiocyanatofluoresceinSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-CHEBI:37918DTXSID80892440I223NX31W9Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 3',6'-dihydroxy-5-isothiocyanato-5 IsothiocyanatofluoresceinFluorescein 5 isothiocyanate
Show more names
Fluorescein isothiocyanate isomer5-FLUORESCEIN ISOTHIOCYANATEFluorescein isothiocyanate isomer I, tech gradeFITC-IFluorescein isothiocyanate IFluorescein isothiocyanate,Isomer I(FITC)
Fluorescein 5 isothiocyanate HydrochlorideHydrochloride, Fluorescein-5-isothiocyanateRefChem:140896DTXCID3029368222-042-0FITCFluorescein isothiocyanate isomer I3',6'-dihydroxy-5-isothiocyanato-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

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

Experimental & physicochemical properties

Physical DescriptionOrange solid; [Merck Index] Orange powder; [Alfa Aesar MSDS]

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 2 items

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

Hazards SummaryCauses cutaneous sensitization (experimental) and effects on inflammation in 3-day intermittent dermal studies of mice; [RTECS] May cause irritation; May cause skin and respiratory sensitization; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Sens. 1 (100%);Resp. Sens. 1 (100%)

Toxicology

Treatment · 1 item

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 · 1 item

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)

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 item

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)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

Regulatory information

Regulatory Information · 2 items

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

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 · 1 item

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 · 2 items

Used as a fluorescent indicator to probe biological systems and monitor sewage; [Merck Index]

Fluorescein isothiocyanate is used in flow cytometry. (L552)

General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-5-isothiocyanato-: ACTIVE
Applications · 3 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Additional notes · 1 item

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

82 records

Compound notes

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