Fluorescein-5-thiosemicarbazide - ≥95% , CAS No.76863-28-0

CAS: 76863-28-0 Cat. No.: F131546 Molecular Weight: 421.43

GRADE & PURITY ≥95%

Synonyms

PD044163 | MEUCHQDLZYLNQY-UHFFFAOYSA-N | 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxo-xanthen-9-yl)benzoic acid | 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid | Fluorescein-5-thiosemicarbazide | SCHEMBL412012 | DTXSID60397968

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Fluorescein-5-thiosemicarbazide is used in labeling of cell-surface functional groups (glycophorins). It is a cell impermeant fluorescent probe useful for determining protein and peptide topology on the cell surface
A compound used to label cell-surface functional groups

application：

Fluorescein-5-thiosemicarbazide can be used as a fluorescent labeling reagent to label:

Cell-surface functional groups (glycophorins) in the study of the effect of deoxygenation in the red blood cell membrane.

Saccharides applicable in polysaccharide imaging in live cells.

Chondroitin sulfate nanogels applicable in cell-specific drug delivery applications.

Specifications

Synonyms

PD044163 | MEUCHQDLZYLNQY-UHFFFAOYSA-N | 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxo-xanthen-9-yl)benzoic acid | 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid | Fluorescein-5-thiosemicarbazide | SCHEMBL412012 | DTXSID60397968

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Fluorescent tag for labeling of cell-surface functional groups (glycophorins). Also used as a probe for detecting protein carbonyl derivatives.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504762792
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762792
• Canonical Smiles: C1=CC(=C(C=C1NC(=S)NN)C(=O)O)C2=C3C=CC(=O)C=C3OC4=C2C=CC(=C4)O
• IUPAC Name: 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• InChIKey: MEUCHQDLZYLNQY-UHFFFAOYSA-N
• INCHI: 1S/C21H15N3O5S/c22-24-21(30)23-10-1-4-13(16(7-10)20(27)28)19-14-5-2-11(25)8-17(14)29-18-9-12(26)3-6-15(18)19/h1-9,25H,22H2,(H,27,28)(H2,23,24,30)
• Isomeric SMILES: C1=CC(=C(C=C1NC(=S)NN)C(=O)O)C2=C3C=CC(=O)C=C3OC4=C2C=CC(=C4)O
• WGK Germany: 3
• Molecular Weight: 421.43
• Reaxy-Rn: 15488949
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=15488949&ln=

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 1-hydroxy-2-unsubstituted benzenoids Thiosemicarbazides Heteroaromatic compounds Cyclic ketones Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Organosulfur compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthene - Benzoic acid or derivatives - Benzoic acid - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Thiosemicarbazide - Heteroaromatic compound - Cyclic ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Oxacycle - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - 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: Soluble in DMF and Water,
• Sensitivity: Light sensitive
• Molecular Weight: 421.400 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 421.073 Da
• Monoisotopic Mass: 421.073 Da
• Topological Polar Surface Area: 166.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 852.000
• 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. Shuxin Jiang, Huanan Yin, Xiaohui Qi, Weiguo Song, Weiwei Shi, Jiaojiao Mou, Jie Yang.  (2020)  Immunomodulatory effects of fucosylated chondroitin sulfate from Stichopus chloronotus on RAW 264.7 cells.  CARBOHYDRATE POLYMERS,      [PMID:33142629] [10.1016/j.carbpol.2020.117088]