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Desogestrel

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Identification
Molecular formula
C22H30O2
CAS number
54024-22-5
IUPAC name
(3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
State
State

Desogestrel typically exists as a solid at room temperature. Its stability in solid form is advantageous for its storage and formulation in contraceptive applications.

Melting point (Celsius)
109.50
Melting point (Kelvin)
382.65
Boiling point (Celsius)
355.30
Boiling point (Kelvin)
628.45
General information
Molecular weight
310.48g/mol
Molar mass
310.4820g/mol
Density
1.1100g/cm3
Appearence

Desogestrel is a white crystalline powder that exhibits no distinct odor. Its physical form is typically seen as carefully milled crystalline powder for pharmaceutical formulations.

Comment on solubility

Solubility of (3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol

The solubility of complex organic compounds such as (3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol can be influenced by various factors. The intricate molecular structure, which includes multiple stereocenters and functional groups, often leads to unique solubility properties. Here are some key points regarding the solubility of this compound:

  • Molecular Structure: The presence of multiple rings and functional groups can either enhance or impede solubility in different solvents.
  • Polarity: Generally, compounds that possess polar functional groups, such as hydroxyl (-OH) groups, tend to have increased solubility in polar solvents like water.
  • Hydrophobic Regions: The compound's hydrophobic sections may limit its solubility in aqueous environments, leading to better solubility in organic solvents such as ethanol or dichloromethane.
  • Temperature: Increased temperature often enhances solubility, allowing more of the compound to dissolve in a given solvent.
  • Intermolecular Forces: Hydrogen bonding and van der Waals forces play a significant role in determining the solubility of this compound in various solvents.

In summary, the solubility of (3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol is likely to be specific to certain environments. Understanding the interactions between the compound and different solvents is crucial for predicting its behavior in both laboratory and industrial applications.

Interesting facts

Interesting Facts About (3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol

This compound is a fascinating example of a complex organic molecule with remarkable structural features. It belongs to a class of compounds known as steroids, characterized by a multi-cyclic structure and a variety of functional groups that significantly influence its chemical behavior and biological activity.

Structural Characteristics

  • Complex stereochemistry: The compound's stereocenters define its spatial configuration, impacting its interaction with biological systems.
  • Presence of diynyl groups: The terminal -C≡C-C≡C- moieties contribute to its reactivity, making it an interesting target for organic synthesis.
  • Multi-cyclo structure: The intricate arrangement of carbon rings is critical for its pharmacological properties.

Biological Significance

This compound is of particular interest in medicinal chemistry due to its potential applications:

  • Hormonal activity: Compounds of this type often exhibit hormonal properties, potentially influencing various physiological pathways.
  • Anticancer research: The unique structure makes it a candidate for further studies into anticancer drug development, particularly in targeting specific cancer cell pathways.
  • Steroid mimics: Understanding its interactions can help in the design of steroid-like drugs with fewer side effects.

Quote to Ponder

As noted by renowned chemist "The beauty of chemistry lies in the complexity of its structures, each telling a unique story of the universe's creativity."

In conclusion, the rich structural and functional attributes of (3S,8R,9S,10R,13S,14S,17S)-17-buta-1,3-diynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol make it an intriguing subject for both research and application in various fields, including pharmacology and organic synthesis.

Synonyms
ANDROST-5-ENE-3-beta,17-beta-DIOL, 17-alpha-BUTADIYNYL-
2010-48-2
BRN 2165143
17-alpha-Butadiynylandrost-5-ene-3-beta,17-beta-diol
17-alpha-Butadiynyl-3-beta,17-beta-dihydroxy-5-androsten-17-one
DTXSID80173923