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Etoposide

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Identification
Molecular formula
C29H32O13N
CAS number
33419-42-0
IUPAC name
[(2R,3R,5R,8R,10R,17S)-8-acetoxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
State
State

At room temperature, Etoposide is typically in a solid state.

Melting point (Celsius)
234.00
Melting point (Kelvin)
507.00
Boiling point (Celsius)
760.00
Boiling point (Kelvin)
1 033.00
General information
Molecular weight
588.56g/mol
Molar mass
588.5620g/mol
Density
1.6500g/cm3
Appearence

Etoposide appears as a white to yellow crystalline powder. It is known for its slightly bitter taste and is practically insoluble in water, soluble in methanol, and sparingly soluble in alcohol.

Comment on solubility

Solubility Insights

The solubility of the compound [(2R,3R,5R,8R,10R,17S)-8-acetoxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate can be characterized by several important factors:

  • Polar vs. Nonpolar: The presence of multiple hydroxyl (-OH) and methoxy (-OCH3) groups indicates a degree of polarity which can enhance solubility in polar solvents like water.
  • Hydrophobic Regions: Even with polar functional groups, the complex hydrocarbon structure may render the compound less soluble in water and more soluble in organic solvents such as ethanol or methanol.
  • Intermolecular Interactions: Hydrogen bonding capabilities due to hydroxyl groups might improve solubility in polar solvents, while steric hindrance and molecular size can impede it.
  • pH Dependency: The solubility may vary with pH, particularly for the acidic benzoate moiety which might dissociate in alkaline conditions, increasing solubility.

Overall, while the intricate structure of this compound suggests potential hybrid solubility characteristics, practical solubility behavior should be assessed experimentally for precise determinations. As with many large organic molecules, solubility can be influenced by a multitude of factors, and thus it remains a fascinating area for further exploration.

Interesting facts

Interesting Facts about the Compound

This fascinating compound is a member of a larger class of organic molecules known for their intricate structures and profound biological activities. Often found in natural sources, compounds like this one possess significant pharmaceutical potential.

Structural Complexity

The compound exhibits a complex architecture, which includes the following notable features:

  • Multiple Functional Groups: With several hydroxyl and methoxy groups, its reactivity and interactions with biological systems can be quite diverse.
  • Stereochemistry: The presence of multiple chiral centers suggests that this compound may exhibit stereoselectivity in its interactions, making its biological effects dependent on its 3D orientation.
  • Cyclic Systems: The inclusion of a hexacyclic framework indicates a potential for interesting conformational dynamics that can impact its behavior and function.

Biological Significance

Compounds like this are often investigated for their therapeutic properties. Some of the possible areas of interest include:

  • Antimicrobial Activity: There’s considerable research into how similar compounds inhibit the growth of various pathogens.
  • Anti-inflammatory Effects: The presence of multiple hydroxyl groups may contribute to reduction in inflammation, providing potential benefits in treating conditions like arthritis.
  • Potential Anticancer Properties: Some related compounds have shown efficacy in cancer models, suggesting further investigation for therapeutic applications may be warranted.

Research Perspectives

From the viewpoint of a chemist or pharmaceutical researcher, this compound’s synthesis and functionalization present intriguing challenges and opportunities:

  • Targeted Synthesis: Crafting this intricate molecule requires advanced synthetic techniques, highlighting the importance of mastering organic synthesis.
  • Mechanistic Studies: Understanding how this compound interacts with biological systems can provide insights into drug development and pharmacology.
  • Modification Potential: Its structural features offer pathways for modification which can lead to the discovery of new derivatives with varied bioactivity.

In summary, this compound is not only a fascinating example of structural complexity and biological potential but also serves as a valuable subject for ongoing research in the field of organic and medicinal chemistry.

Synonyms
8006-38-0
Mild aconitate
Mild aconitine
ACONITINE, AMORPHOUS
AKOS032948369
[(2R,3R,5R,8R,10R,17S)-8-acetyloxy-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate