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Hydroxyprogesterone

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Identification
Molecular formula
C21H30O3
CAS number
68-96-2
IUPAC name
(16R)-17-acetyl-16-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
State
State

Hydroxyprogesterone is typically found in a solid state at room temperature.

Melting point (Celsius)
226.00
Melting point (Kelvin)
499.00
Boiling point (Celsius)
388.00
Boiling point (Kelvin)
661.00
General information
Molecular weight
330.47g/mol
Molar mass
330.4650g/mol
Density
1.1710g/cm3
Appearence

Hydroxyprogesterone is a white to creamy white, crystalline powder with no significant odor. It is relatively stable under normal storage conditions.

Comment on solubility

Solubility Insights

The compound (16R)-17-acetyl-16-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one exhibits interesting solubility characteristics, which are influenced by its complex structure and functional groups.

Key Factors Affecting Solubility

  • Polarity: The presence of hydroxyl (-OH) and acetyl (-C(=O)CH3) groups can enhance the polarity of the compound, making it more likely to dissolve in polar solvents.
  • Hydrogen Bonding: The hydroxyl group can engage in hydrogen bonding, increasing solubility in alcohols and other hydrogen bonding solvents.
  • Hydrophobic Interactions: The hydrophobic dodecahydrocyclopenta[a]phenanthrene moiety may create challenges for solubility in polar solvents, while promoting solubility in non-polar solvents like hexane or benzene.

Solubility Behavior

It's important to consider the following solubility behavior when working with the compound:

  • This compound is more likely to be soluble in organic solvents such as ethyl acetate and chloroform due to their ability to interact with both polar and non-polar regions.
  • In contrast, it may be poorly soluble in highly polar solvents like water, due to the competing hydrophobic interactions.

In conclusion, while the solubility of (16R)-17-acetyl-16-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one can be influenced by various factors, understanding its specific interactions with solvents is crucial for effective applications in research and industry.

Interesting facts

Interesting Facts about (16R)-17-acetyl-16-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

This compound, often classified within the realm of steroids, possesses a complex structure that contributes to its fascinating chemical behavior and biological activity. Here are some compelling aspects to consider:

  • Steroidal Framework: The structure exemplifies a steroid-like framework, indicating its potential biological significance and interaction with steroid receptors in living organisms.
  • Hydroxyl Group Influence: Highlighting the presence of a hydroxyl group (–OH) at position 16, this functional group can enhance hydrogen bonding with biological molecules, potentially increasing solubility in biological systems.
  • Acetyl Functionality: The acetyl group (–COCH3) at position 17 can be crucial for the compound's reactivity and may play an important role in metabolic processes.
  • Dimethyl Substituents: The dimethyl groups at positions 10 and 13 are significant as they can influence the compound's steric hindrance and conformational stability, affecting its receptor binding abilities.
  • Origins in Natural Compounds: Compounds similar to this one are often found in nature, particularly in various plant species, and are studied for their potential therapeutic applications, including anti-inflammatory and anti-cancer properties.

In addition to its structural complexity, this compound exemplifies the interplay between structure and function. As chemists, we can appreciate how slight alterations in molecular architecture can lead to drastically different biological effects.

In the words of legendary chemist Linus Pauling, "The secret of life is to look at things from a different angle." This compound stands as a testament to that principle, showcasing the beauty and potential of chemical diversity.