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Clobetasol Propionate

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Identification
Molecular formula
C25H32ClO5
CAS number
25122-46-7
IUPAC name
(9S,11S,14S,17R)-6-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one
State
State

At room temperature, clobetasol propionate is in the solid state, specifically appearing as a dried crystalline powder.

Melting point (Celsius)
195.00
Melting point (Kelvin)
468.00
Boiling point (Celsius)
545.80
Boiling point (Kelvin)
819.00
General information
Molecular weight
467.13g/mol
Molar mass
467.3750g/mol
Density
1.2500g/cm3
Appearence

Clobetasol propionate appears as a white to almost white crystalline powder. It is practically insoluble in water and freely soluble in acetone and in methanol. Clobetasol propionate is a synthetic corticosteroid used for its anti-inflammatory effects.

Comment on solubility

Solubility Characteristics

The solubility of the compound (9S,11S,14S,17R)-6-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopentaphenanthren-3-one can be influenced by its structural attributes. Here are some key points regarding its solubility:

  • Polarity: The presence of multiple hydroxyl groups (-OH) and a chloro group suggests potential for increased polarity, which can enhance solubility in polar solvents like water.
  • Hydrophilic vs. Hydrophobic Balance: While the -OH groups contribute to hydrophilicity, the hydrophobic cyclic structures may reduce overall water solubility.
  • Solvent Interactions: This compound might show differing solubility in organic solvents such as ethanol or acetone compared to aqueous solutions, highlighting its dual-character nature.
  • Complexation and Binding: The molecular structure may facilitate interactions with other compounds, influencing solubility via complex formation.

In conclusion, the solubility of (9S,11S,14S,17R)-6-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopentaphenanthren-3-one is likely to be nuanced and dependent on the solvent environment, with an inclination towards differential solubility that merits further investigation.

Interesting facts

Interesting Facts about (9S,11S,14S,17R)-6-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one

This unique compound, belonging to the class of steroids, exhibits a complex structure that incorporates a variety of functional groups. Here are some intriguing aspects of this compound:

  • Biological Significance: The structural features of this compound suggest it may play a role in biological systems, particularly as a potential therapeutic agent.
  • Chirality: The presence of multiple chiral centers indicates a rich potential for stereoisomerism, which can greatly influence the biological activity and interactions of the compound.
  • Hydroxyl Groups: With both 11 and 17 locations showing hydroxyl (-OH) groups, these contribute to the compound's reactivity and the ability to form hydrogen bonds, enhancing solubility in biological systems.
  • Chlorine Atom: The incorporation of chlorine can alter the compound's lipophilicity and biological effects, often enhancing binding affinities in target proteins or receptors.
  • Hydroxyacetyl Functionality: The 2-hydroxyacetyl substituent suggests potential implications in metabolic pathways, as such moieties are frequently involved in enzymatic reactions.
  • Structural Complexity: The cyclopenta[a]phenanthren backbone represents a fascinating interplay between cyclic and polycyclic structures in organic chemistry.

Overall, the detailed structural attributes of (9S,11S,14S,17R)-6-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one not only pique the interest of chemists but also highlight the intricacies of steroid chemistry and its applications in medicinal fields. As with many complex compounds, the bridge between structure and function remains a critical avenue for future research.