2-Deoxy-2-fluoro-D-glucopyranose - Moligand™,≥98% , CAS No.29702-43-0

CAS: 29702-43-0 Cat. No.: D155079 Molecular Weight: 182.15 EC Number: 636-698-4

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2R,3S,4R,5R)-2-fluoro-3,4,5,6-tetrahydroxyhexanal | C6H11FO5 | 2-Fluoro-2-deoxy-D-glucopyranose | .ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-2-FLUORO | FLUDEOXYGLUCOSE [USP-RS] | Q27121494 | CHEBI:49135 | D3023 | HY-141637 | J-508317 | 2-Fluoro-2-deoxy-D-glucose |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

2-Fluoro-2-deoxy-D-glucose is non-toxic and a structural analog of glucose, significantly inhibiting glycosylation. As a glucose analog, uptake of 2-Fluoro-2-deoxy-D-glucose is rapid in brain and heart cells.

2-Fluoro-2-deoxy-D-glucose can be taken up by cells but does not undergo metabolic glycolysis.

Specifications

Synonyms

(2R, 3S, 4R, 5R)-2-fluoro-3, 4, 5, 6-tetrahydroxyhexanal | C6H11FO5 | 2-Fluoro-2-deoxy-D-glucopyranose | .ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-2-FLUORO | FLUDEOXYGLUCOSE [USP-RS] | Q27121494 | CHEBI:49135 | D3023 | HY-141637 | J-508317 | 2-Fluoro-2-deoxy-D-glucose |

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Glucose analog that inhibits cellular glycosylation.

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.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504757641
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757641
• Canonical Smiles: C(C(C(C(C(C=O)F)O)O)O)O
• IUPAC Name: (2R,3S,4R,5R)-2-fluoro-3,4,5,6-tetrahydroxyhexanal
• InChIKey: AOYNUTHNTBLRMT-SLPGGIOYSA-N
• INCHI: 1S/C6H11FO5/c7-3(1-8)5(11)6(12)4(10)2-9/h1,3-6,9-12H,2H2/t3-,4+,5+,6+/m0/s1
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)F)O)O)O)O
• Molecular Weight: 182.15
• Reaxy-Rn: 32640304
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=32640304&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Aldehydes
          • Level6 Beta-hydroxy aldehydes

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Aldehydes
• Direct Parent: Beta-hydroxy aldehydes
• Alternative Parents: Secondary alcohols Fluorohydrins Polyols Primary alcohols Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Beta-hydroxy aldehyde - Secondary alcohol - Halohydrin - Fluorohydrin - Polyol - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organofluoride - Organohalogen compound - Alkyl halide - Alkyl fluoride - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as beta-hydroxy aldehydes. These are organic compounds containing an aldehyde substituted with a hydroxy group on the second carbon atom.
• External Descriptors: 2-deoxy-2-fluoro-D-glucose

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

• Sensitivity: Heat Sensitive
• Specific Rotation[α]: 63° (C=1,dilute NH3aq.)
• Melt Point(°C): 176 °C
• Molecular Weight: 182.150 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 182.059 Da
• Monoisotopic Mass: 182.059 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 142.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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. Gaochao Lv, Yinxing Miao, Yinfei Chen, Chunmei Lu, Xiuting Wang, Minhao Xie, Ling Qiu, Jianguo Lin.  (2021)  Promising potential of a 18F-labelled small-molecular radiotracer to evaluate PD-L1 expression in tumors by PET imaging.  BIOORGANIC CHEMISTRY,      [PMID:34426150] [10.1016/j.bioorg.2021.105294]