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Dexamethasone

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Identification
Molecular formula
C22H29ClO5
CAS number
50-02-2
IUPAC name
(9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
State
State

Dexamethasone is typically observed as a solid at room temperature.

Melting point (Celsius)
262.00
Melting point (Kelvin)
535.15
Boiling point (Celsius)
572.20
Boiling point (Kelvin)
845.35
General information
Molecular weight
392.47g/mol
Molar mass
392.4680g/mol
Density
1.4240g/cm3
Appearence

Dexamethasone appears as a white to practically white, crystalline powder. It may also appear in the form of granules. It is slightly soluble in water, freely soluble in alcohol, in dioxane, and in methanol, and sparingly soluble in acetone.

Comment on solubility

Solubility of (9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

The solubility of the compound (9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one is influenced by several factors, making it an intriguing subject for study. Here are key points to consider:

  • Polarity: Due to the presence of multiple hydroxyl (-OH) groups, this compound exhibits enhanced polarity, which generally increases its solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups can engage in hydrogen bonding with solvent molecules, further promoting solubility in polar environments.
  • Non-polynomial Character: Despite its polar nature, the compound has a significant hydrophobic character due to its complex ring structure. This can limit solubility in non-polar solvents.
  • Temperature Effects: Like many organic compounds, solubility can be temperature-dependent. Increased temperature may enhance the solubility in solvents.

In summary, the solubility of (9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one is a complex interplay of its functional groups and structure. Its solubility is optimized in polar solvents, yet the inherent hydrophobic regions present unique challenges for dissolving in non-polar environments. Thus, understanding its solubility behavior could be essential for its applications in various chemical contexts.

Interesting facts

Interesting Facts about (9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

This intriguing compound, often associated with the realm of medicinal chemistry, showcases the remarkable interplay between structure and biological activity. Here are some engaging facts about this fascinating molecule:

  • Synthetic Identity: This compound is a synthetic derivative, which highlights the significance of chemical modifications in developing pharmaceuticals. The specificity of its stereochemistry (noted as 9R and 17S) is crucial for its biological activity.
  • Chlorine's Role: The incorporation of a chlorine atom in its structure contributes to the compound's lipophilicity, which often enhances the permeability through cell membranes, making it potentially effective in therapeutic applications.
  • Dihydroxy Groups: The presence of two hydroxyl (-OH) groups not only influences the compound's polarity but also provides sites for potential interactions with biological targets, making it a prime candidate for further investigation in drug design.
  • Tertiary Carbon Atoms: The trimethyl groups suggest that this compound may exhibit unique steric interactions, potentially affecting enzyme recognition and binding, thereby influencing its efficacy as a drug.
  • Cyclic Structure: The presence of a polycyclic structure adds complexity and can play a role in how the compound interacts with various biological systems, revealing insights into the importance of cyclization in drug development.

In summary, the intricate structure of (9R,17S)-9-chloro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one serves as a testament to the artistry and science embedded in compound design. Its unique features not only underline the importance of chirality and substituent effects in medicinal chemistry but also hint at its potential as a pharmaceutical agent in future explorations.