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Chlormadinone acetate

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Identification
Molecular formula
C23H29ClO4
CAS number
302-22-7
IUPAC name
[(8R,9S,10R,13S,14S,17S)-4-chloro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
State
State

Chlormadinone acetate is a solid at room temperature, typically supplied as a pure crystalline powder.

Melting point (Celsius)
200.00
Melting point (Kelvin)
473.15
Boiling point (Celsius)
405.90
Boiling point (Kelvin)
679.05
General information
Molecular weight
404.93g/mol
Molar mass
404.9670g/mol
Density
1.2701g/cm3
Appearence

Chlormadinone acetate appears as a white or almost white crystalline powder. It is practically insoluble in water, but soluble in organic solvents like ethanol and acetone.

Comment on solubility

Solubility Characteristics

The solubility of the compound [(8R,9S,10R,13S,14S,17S)-4-chloro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate is influenced by several factors that are typical of organic compounds, particularly those with complex structures and multiple functional groups. Understanding its solubility can help in various applications, including formulation and synthesis.

Key Factors Influencing Solubility:

  • Polarity: The presence of polar functional groups, such as the acetate group, suggests potential interactions with polar solvents like water, although the overall large non-polar hydrocarbon framework may reduce solubility.
  • Hydrophobic Interactions: The extensive hydrophobic character due to the fused ring system likely limits solubility in polar solvents while enhancing solubility in non-polar organic solvents.
  • Temperature Effects: As with many organic compounds, solubility may increase with temperature, making hot solvent usage effective.
  • Solvent Type: The melting point and solubility can vary widely depending on whether non-polar (e.g., hexane) or polar solvents (e.g., ethanol) are used.

In summary, while the compound may exhibit some degree of solubility in polar solvents owing to its functional groups, its overall solubility is likely limited by the bulkiness and hydrophobic nature of its structure. Thus, it may be best dissolved in a mixture of solvents or in non-polar conditions. Knowing these solubility parameters is crucial for optimizing its usage in chemical applications.

Interesting facts

Interesting Facts about the Compound

This compound, known for its complex structure, is a derivative of a steroid framework. Here are some fascinating insights:

  • Steroid Family: This compound belongs to the class of steroids, which are organic compounds characterized by a core structure of four fused carbon rings. Steroids play crucial roles in biological systems, including hormones, signaling molecules, and membrane components.
  • Chirality: The presence of multiple chiral centers (indicated by the stereochemistry in the compound's name) means that this molecule can exist in various stereoisomeric forms. This chirality is essential in determining the biological activity of similar compounds and highlights the significance of stereochemistry in drug design.
  • Biological Applications: Compounds derived from similar steroid structures often have pharmacological importance. They can function as anti-inflammatory agents, contraceptives, or anabolic sterols. The acetate group in this compound may contribute to its solubility and absorption profile, making it a candidate for therapeutic formulations.
  • Research Significance: The intricate architecture of this compound presents ample opportunity for synthesis and modification in laboratories. Scientists often explore how slight alterations in structure can lead to significant changes in activity and interactions, paving the way for new drug discovery and development.
  • Cyclopenta[a]phenanthrene Core: The specific carbon framework within cyclopenta[a]phenanthrenes adds unique properties that can influence the compound’s reactivity and potential interactions with biomolecules.

In summary, this compound showcases the beauty of organic chemistry and the complexity of biological systems. As scientists continue to explore and innovate, compounds like this offer a wealth of potential for advancements in medicine and understanding human biology.

Synonyms
Clostebol acetate
855-19-6
Megagrisevit
Anabolit
Stearanabol
Sterabol
Testomed
Test-anabol
Chlorotestosterone acetate
4-Chlortestosterone acetate
Clostene
Alfa-Trofodermin
NSC 72159
17beta-Acetoxy-4-chloroandrost-4-en-3-one
Testosterone, 4-chloro-, acetate
EINECS 212-720-4
780ZZX4P14
Clostebol acetate (BAN)
Clostebol 17 beta-acetate
CLOSTEBOL ACETATE [MI]
DTXSID00234702
CLOSTEBOL ACETATE [MART.]
CLOSTEBOL ACETATE [WHO-DD]
Androst-4-en-3-one, 17-(acetyloxy)-4-chloro-, (17beta)-
ANDROST-4-EN-3-ONE, 4-CHLORO-17-beta-HYDROXY-, ACETATE
Clostebol acetate [BAN]
4-CHLORO-3-OXOANDROST-4-EN-17.BETA.-YL ACETATE
CLOSTEBOL ACETATE (MART.)
4-CHLORO-17.BETA.-HYDROXYANDROST-4-EN-3-ONE ACETATE
DTXCID90157193
4-CHLORO-3-OXOANDROST-4-EN-17BETA-YL ACETATE
4-CHLORO-17BETA-HYDROXYANDROST-4-EN-3-ONE ACETATE
(8R,9S,10R,13S,14S,17S)-4-chloro-3-oxoandrost-4-en-17beta-yl acetate
212-720-4
Steranabol
Macrobin
4-Chlorotestosterone acetate
4-Chlorotestosterone 17-acetate
[(8R,9S,10R,13S,14S,17S)-4-chloro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CHEBI:81712
NSC-72159
Clostebol Acetat
Androst-4-en-3-one, 17-(acetyloxy)-4-chloro-, (17b)-
Clostebol Acetate (1mg/ml in Acetonitrile)
UNII-780ZZX4P14
Trofodermin (TN)
4-Chloro-testosterone acetate
SCHEMBL216171
CHEMBL519327
Androst-4-en-3-one, 4-chloro-17.beta.-hydroxy-, acetate
4-chlorotestosterone acetate;[(8R,9S,10R,13S,14S,17S)-4-chloro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
Androst-4-en-3-one, 17-(acetyloxy)-4-chloro-, (17.beta.)-
NSC72159
AKOS007930359
AKOS015894896
FC20520
NS00009947
17.beta.-Acetoxy-4-chloroandrost-4-en-3-one
4-Chloro-17.beta.-acetoxyandrost-4-en-3-one
C18374
D07732
4-Chlorotestosterone acetate testosterone 17-acetate
Q27155574
4-Chloro-3-oxoandrost-4-en-17-yl acetate, (17.beta)- #
(8R,9S,10R,13S,14S,17S)-4-chloro- 3-oxoandrost-4-en-17beta-yl acetate
4-Chloro-17b-hydroxy-androst-4-en-3-one acetate;4-Chlorotestosterone acetate