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Etoposide

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Identification
Molecular formula
C29H32O13
CAS number
33419-42-0
IUPAC name
[(6S,9S,10S,12R,13S,14S,16R,19S,22S,23S,25R)-16-acetoxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-(2-methylbutanoyloxy)-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-13-yl] 2-hydroxy-2-methyl-butanoate
State
State

At room temperature, Etoposide is in a solid state, existing as a crystalline powder. Its solid form makes it suitable for conversion into a liquid solution for medical uses via dissolution in appropriate solvents.

Melting point (Celsius)
231.00
Melting point (Kelvin)
504.15
Boiling point (Celsius)
115.00
Boiling point (Kelvin)
388.15
General information
Molecular weight
588.57g/mol
Molar mass
588.5730g/mol
Density
1.4608g/cm3
Appearence

Etoposide typically appears as an off-white to white crystalline powder. It is sensitive to light and should be stored in a container that protects it from light exposure. The compound is often dissolved in dimethyl sulfoxide (DMSO) for use in pharmaceutical formulations.

Comment on solubility

Solubility of the Compound

The solubility of the compound known as [(6S,9S,10S,12R,13S,14S,16R,19S,22S,23S,25R)-16-acetoxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-(2-methylbutanoyloxy)-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-13-yl] 2-hydroxy-2-methyl-butanoate is influenced by a variety of factors:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that this compound may have significant polarity, which typically enhances solubility in polar solvents such as water.
  • Functional Groups: The acetoxy and methylbutanoate groups can interact favorably with solvents, potentially increasing solubility in organic solvents.
  • Size and Structure: The large and complex molecular structure, indicated by the presence of multiple cycloalkane rings and functional groups, might hinder solubility due to steric hindrance.

In general, it can be stated that:

  1. The compound is likely to show higher solubility in organic solvents such as alcohols and esters due to hydrophobic interactions with its larger carbon frameworks.
  2. It might have moderate solubility in water because of the hydroxyl functional groups facilitating hydrogen bonding.
  3. Factors like temperature, pH, and the presence of other solutes can further affect its solubility behavior.

Understanding the solubility of this compound is crucial for practical applications, especially in fields such as pharmaceuticals and materials science, where solvent interactions dictate performance and stability.

Interesting facts

Interesting Facts about the Compound

This compound presents an intriguing structure as it belongs to a class of molecules known for their biologically significant activities. Notably, compounds with such complex polycyclic frameworks often exhibit:

  • Pharmacological Potential: The intricate structure suggests that it may have useful pharmacological properties. Many compounds in similar categories are involved in activities such as anti-inflammatory and anticancer actions.
  • Natural Origin: The unique configuration of this molecule hints at a natural origin. Many complex compounds are derived from natural sources, like plants and microorganisms, serving as a foundation for drug discovery.
  • Stereochemistry Significance: The specification of stereochemical configurations (S and R) reveals the importance of 3D orientation in molecular interactions, which can significantly influence biological activity!
  • Structural Complexity: The term "heptacyclo" indicates that the molecule contains seven interconnected cycles, which adds to the challenges associated with synthesis and characterization of such compounds.

As a chemist or a student studying organic chemistry, one might be fascinated to explore the following aspects:

  • The synthesis pathways and difficulties involved in creating such a complex molecule.
  • The stability and reactivity patterns associated with its unique functional groups.
  • Potential applications in pharmacology and materials science.

As stated in illuminating research, "The complexity and functionality of bioactive compounds are often reflected in their intricate structures." Therefore, studying this compound could pave the way for innovative research breakthroughs, especially in medicinal chemistry.

Synonyms
SCHEMBL14052394
DTXSID40971386
7-(Acetyloxy)-4,14,16,20-tetrahydroxy-3-[(2-methylbutanoyl)oxy]-4,9-epoxycevan-15-yl 2-hydroxy-2-methylbutanoate