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Ethynodiol diacetate

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Identification
Molecular formula
C22H28ClO
CAS number
297-76-7
IUPAC name
(17R)-17-(2-chloroethynyl)-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, ethynodiol diacetate is in solid state.

Melting point (Celsius)
170.00
Melting point (Kelvin)
443.15
Boiling point (Celsius)
375.00
Boiling point (Kelvin)
648.15
General information
Molecular weight
344.91g/mol
Molar mass
344.9130g/mol
Density
1.2000g/cm3
Appearence

Ethynodiol diacetate typically appears as a white to creamy-white crystalline powder. It is practically odorless and tends to clump together if exposed to high humidity.

Comment on solubility

Solubility of (17R)-17-(2-chloroethynyl)-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

The solubility of (17R)-17-(2-chloroethynyl)-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one can be complex and is influenced by several factors. Here are some key points to consider:

  • Polarity: The presence of hydroxyl (-OH) and chloroethynyl functional groups suggests some polarity, which may enhance solubility in polar solvents like water and alcohols.
  • Non-polar regions: The large hydrocarbon structure may lead to strong hydrophobic interactions, potentially decreasing solubility in water.
  • Solvent Effects: This compound may exhibit varying solubility in different solvents, making it more soluble in organic solvents such as dichloromethane or dimethyl sulfoxide than in aqueous solutions.
  • Temperature Influence: Increasing temperature often increases solubility for many organic compounds, potentially affecting the solubility profile of this compound.

As a general guideline, "the more symmetric and non-polar the compound, the lower the solubility in water," which could apply to this compound due to its dodecahydrocyclopenta[a]phenanthren structure. Further experimental studies would be beneficial to quantify its solubility under various conditions, providing more clarity on its practical applications.

Interesting facts

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

This compound, often referred to in research settings, harbors a variety of intriguing features:

  • Therapeutic Potential: Compounds with similar structures have been investigated for their potential anticancer properties, showcasing a promising area of medical chemistry.
  • Synthetic Pathways: The synthesis of this molecule involves sophisticated organic reactions which could be a fascinating topic of study in synthetic chemistry courses.
  • Chirality: The designation (17R) indicates chirality, allowing it to have unique properties and interact differently in biological systems compared to its counterpart (17S).
  • Mechanism of Action: Understanding how modifications, such as the incorporation of a chloroethynyl group, can alter the biological activity of steroid-like compounds provides valuable insights into drug design.
  • Structure-Activity Relationship (SAR): The precise arrangement of functional groups around the dodecahydrocyclopenta[a]phenanthren backbone is crucial for determining the compound's efficacy and binding affinity to biological targets.

The study of this compound opens doors not only to advancements in medicinal chemistry but also to challenges in environmental chemistry, particularly with the introduction of halogenated compounds. As research continues, the implications of such compounds for future therapeutics could be profound. As noted by renowned chemists, "the interaction between structure and function is what drives innovation in the field of organic chemistry."

In summary, (17R)-17-(2-chloroethynyl)-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one serves as an exemplar of the dynamic interplay between chemical structure and biological relevance, making it a vital subject of study for both students and professionals alike.