6-TRITC, R-isomer [Tetramethylrhodamine-6-isothiocyanate] - ≥80% , CAS No.80724-20-5

CAS: 80724-20-5 Cat. No.: T131320 Molecular Weight: 443.52 EC Number: 103-354-5

GRADE & PURITY ≥80%

Synonyms

Xanthylium, 9-(2-carboxyisothiocyanatophenyl)-3,6-bis(dimethylamino)- (inner salt) | Tetramethylrhodamine isothiocyanate | 2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-4-isothiocyanatobenzoate | 6-TRITC | 6-TRITC, R-isomer | tetramethylrhodami

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Tetramethylrhodamine isothiocyanate Isomer R (TRITC) is the R isomer of tetramethylrhodamine isothiocyanate and is also known as 6-tetramethylrhodamine isothiocyanate. It is a strongly fluorescent compound soluble in ethanol, methanol, dimethylformamide, dimethylsulfoxide, and water. TRITC is a moderately-sized aminoxanthene dye carrying carboxylic acid and isothiocyanate substituents on the non-planar pendant phenyl ring. It forms a lipophilic cation in acidic pH and a hydrophilic zwitterion around neutral pH. The isothiocyanate group reacts with nucleophilic substituents (e.g., amino, hydroxyl, thiol) of biomolecules, providing the means of attaching a fluorescent label. TRITC also reacts with water and hydroxide ions and is unstable in aqueous solutions. TRITC is commercially available as a zwitterion or as a chloride.

Specifications

Synonyms

Xanthylium, 9-(2-carboxyisothiocyanatophenyl)-3, 6-bis(dimethylamino)- (inner salt) | Tetramethylrhodamine isothiocyanate | 2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-4-isothiocyanatobenzoate | 6-TRITC | 6-TRITC, R-isomer | tetramethylrhodami

Specifications & Purity

≥80%

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥80%

Names and Identifiers

• Canonical Smiles: CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=CC(=C4)N=C=S)C(=O)[O-]
• IUPAC Name: 2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-4-isothiocyanatobenzoate
• InChIKey: OBYNJKLOYWCXEP-UHFFFAOYSA-N
• INCHI: 1S/C25H21N3O3S/c1-27(2)16-6-9-19-22(12-16)31-23-13-17(28(3)4)7-10-20(23)24(19)21-11-15(26-14-32)5-8-18(21)25(29)30/h5-13H,1-4H3
• Isomeric SMILES: CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=CC(=C4)N=C=S)C(=O)[O-]
• Alternate CAS: 95197-95-8
• Molecular Weight: 443.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzopyrans
      • Subclass 1-benzopyrans
        • Level5 Dibenzopyrans
          • Level6 Xanthenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Dibenzopyrans
• Direct Parent: Xanthenes
• Alternative Parents: Benzoic acids Benzoyl derivatives Dialkylarylamines Secondary ketimines Heteroaromatic compounds Amino acids Carboxylic acid salts Isothiocyanates Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Carboxylic acids Organooxygen compounds Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthene - Benzoic acid or derivatives - Benzoic acid - Benzoyl - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Secondary ketimine - Amino acid or derivatives - Amino acid - Carboxylic acid salt - Isothiocyanate - Tertiary amine - Oxacycle - Carboxylic acid derivative - Carboxylic acid - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic oxygen compound - Organic salt - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxide - Organic cation - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: 1 M NH4OH: 10 mg/mL (Faint Red to Very Dark Red to Very Dark Purple solution)
• Sensitivity: Light sensitive
• Molecular Weight: 443.500 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 443.13 Da
• Monoisotopic Mass: 443.13 Da
• Topological Polar Surface Area: 100.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 904.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yong He, Yingran Wang, Yanli Shi, Zhifeng Fu.  (2018)  Molecular recognition strategy for detection and antimicrobial susceptibility testing of Staphylococcus aureus by utilizing teicoplanin and porcine IgG as indicator molecules.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.04.015]