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Bexarotene

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Identification
Molecular formula
C24H29NO2S
CAS number
153559-49-0
IUPAC name
3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid
State
State

At room temperature, Bexarotene is in solid state, typically found as a powder. It is stable under normal temperatures and pressures.

Melting point (Celsius)
230.00
Melting point (Kelvin)
503.15
Boiling point (Celsius)
552.10
Boiling point (Kelvin)
825.30
General information
Molecular weight
348.48g/mol
Molar mass
348.4300g/mol
Density
1.2315g/cm3
Appearence

Bexarotene is typically a white to off-white crystalline powder. It is sparingly soluble in water, which contributes to its appearance.

Comment on solubility

Solubility of 3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid

The solubility of 3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid (C24H29NO2S) is an intriguing aspect of its chemical behavior. This compound, characterized by its complex molecular structure, exhibits varying solubility depending on the solvent used:

  • Aqueous Solubility: Generally, hydroxamic acids display limited solubility in water, and this compound is likely no exception. Its hydrophobic benzenesulfonyl and prop-2-ene moieties may contribute to poor solubility in polar solvents.
  • Solubility in Organic Solvents: In contrast, it may show enhanced solubility in organic solvents such as ethanol, dimethyl sulfoxide (DMSO), or methanol due to its non-polar characteristics.
  • Effect of pH: The solubility could be affected by the pH of the solution, as hydroxamic acids can exist in different ionization states. An increase in the pH may enhance solubility by facilitating deprotonation.

In summary, the solubility of 3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid is influenced by several factors, including:

  1. **Nature of Solvent**: Polar vs. non-polar solvents.
  2. **Molecular Structure**: Presence of hydrophobic groups.
  3. **pH of Solution**: The potential for ionization changes.

Understanding these solubility characteristics is crucial for applications in pharmaceuticals and biochemical settings, where solubility can impact drug bioavailability and efficacy.

Interesting facts

Interesting Facts about 3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid

This compound is a fascinating example of a hydroxamic acid derivative, which showcases the diverse and functional nature of organic molecules in medicinal chemistry. Hydroxamic acids like this one play crucial roles in various biological processes and have been studied for their potential therapeutic applications, particularly in cancer treatment and as enzyme inhibitors.

Key Highlights:

  • Versatile Functional Groups: The presence of a benzenesulfonyl group paired with an amino and hydroxamic acid moiety makes this compound structurally interesting and potentially reactive.
  • Medicinal Chemistry: Compounds containing hydroxamic acid have been explored for use in metal ion chelation, which is vital in both pharmacology and environmental chemistry.
  • Biological Relevance: Hydroxamic acids have shown promise as inhibitors of metalloprotein enzymes, which are implicated in various pathological conditions, including cancer.

Researchers continue to investigate how structural modifications can enhance the specificity and efficacy of similar compounds in targeting diseases. As noted by one prominent chemist, "Understanding the structure-activity relationship in complex organic compounds like these is key to pioneering innovative therapeutic solutions." This makes 3-[4-[benzenesulfonyl(methyl)amino]phenyl]prop-2-enehydroxamic acid not just a chemical curiosity but a potential game-changer in drug development.

Further research into this compound could illuminate new pathways for therapeutic intervention, making it a significant point of study in contemporary chemistry and medicinal applications.