5-Carboxyfluorescein - ≥95% , CAS No.76823-03-5

CAS: 76823-03-5 Cat. No.: C105530 Formula: C₂₁H₁₂O₇ Molecular Weight: 376.32 Beilstein Registry Number: 57037 EC Number: 691-482-7

GRADE & PURITY ≥95%

Synonyms

Q27122687 | 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid | BCP22613 | DTXSID30227642 | 5-FAM | 3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid | AS-32304 | PD012213 | Spiro(isobenzofuran-1(3H),9'-(9H)

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

5-Carboxyfluorescein, also known as 5-FAM, is a green fluorescent product. It is derived from cleavage of 5-Carboxyfluorescein diacetate by intracellular esterases. In viable cells, the fluorescent molecule is impermeable to the cellular membrane.

Specifications

Synonyms

Q27122687 | 3',6'-Dihydroxy-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid | BCP22613 | DTXSID30227642 | 5-FAM | 3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid | AS-32304 | PD012213 | Spiro(isobenzofuran-1(3H),9'-(9H)

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Amine-reactive fluorescent label. 6-FAM isomer. Polar tracer. Covalently labels peptides and proteins. 5-CFDA N-succinimidyl ester and 5-CFDA hydrolytic product.

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

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: 488187777
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187777
• Canonical Smiles: C1=CC2=C(C=C1C(=O)O)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
• IUPAC Name: 3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• InChIKey: NJYVEMPWNAYQQN-UHFFFAOYSA-N
• INCHI: 1S/C21H12O7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)21(15)14-4-1-10(19(24)25)7-13(14)20(26)28-21/h1-9,22-23H,(H,24,25)
• Isomeric SMILES: C1=CC2=C(C=C1C(=O)O)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
• WGK Germany: 3
• Molecular Weight: 376.32
• Beilstein: 57037
• Reaxy-Rn: 57037
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=57037&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: M-phthalic acid and derivatives Diarylethers Phthalides Benzofuranones Isobenzofurans 1-hydroxy-2-unsubstituted benzenoids Dicarboxylic acids and derivatives Lactones Carboxylic acid esters Oxacyclic compounds Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthene - Meta_phthalic_acid - Diaryl ether - Benzofuranone - Phthalide - Isobenzofuranone - Isobenzofuran - Isocoumaran - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Dicarboxylic acid or derivatives - Lactone - Carboxylic acid ester - Oxacycle - Ether - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organic oxygen 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: monocarboxylic acid

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 H2O and DMSO
• Sensitivity: light & Moisture sensitive
• Molecular Weight: 376.300 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 376.058 Da
• Monoisotopic Mass: 376.058 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 637.000
• 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

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Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 76823-03-5, the molecular formula is C21H12O7, and the molecular weight is 376.32 g/mol. InChIKey NJYVEMPWNAYQQN-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.