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Bufotalin

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Identification
Molecular formula
C26H34O6
CAS number
465-21-4
IUPAC name
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
State
State

Bufotalin is typically found in a solid state at room temperature. It is stable under normal ambient conditions and must be handled with care due to its steroidal activity.

Melting point (Celsius)
226.00
Melting point (Kelvin)
499.15
Boiling point (Celsius)
700.00
Boiling point (Kelvin)
973.15
General information
Molecular weight
404.47g/mol
Molar mass
404.4740g/mol
Density
1.3500g/cm3
Appearence

Bufotalin appears as a crystalline solid that is typically white in color. It is an organic compound and, like many steroids, exhibits a complex multi-ring structure that is characteristic of most steroidal saponins. The crystalline nature allows it to form structured, repeating units within a lattice framework.

Comment on solubility

Solubility of (3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

This compound exhibits complex solubility characteristics due to its intricate structure, which combines multiple hydroxyl groups and various cyclic elements. Here are some key aspects to consider regarding its solubility:

  • Water Solubility: The presence of three hydroxyl (-OH) groups suggests a potential for moderate to high water solubility, as hydroxyl groups are polar and can engage in hydrogen bonding with water molecules.
  • Solubility in Organic Solvents: In addition to water, the compound might also be soluble in organic solvents such as ethanol or methanol, owing to the hydrophobic segments within its structure.
  • pH Dependence: The solubility could be influenced by the pH of the solution, as ionization of the hydroxyl groups may enhance solubility in basic conditions.

Overall, while the variety of functional groups suggest a strong potential for solubility in polar solvents, it remains important to consider the balance between hydrophilic and hydrophobic portions of the molecule. Therefore, empirical testing would be essential to accurately quantify its solubility in different media.

Interesting facts

Interesting Facts about (3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

This compound, with a complex structure, is an intriguing example of modern organic synthesis, often found in the study of natural products and pharmaceuticals. Here are some fascinating aspects:

  • Natural Product Origin: Many compounds with similar structures are derived from natural sources, particularly plants and fungi, showcasing the potential for discovering novel medicinal applications.
  • Biological Activity: Compounds like this one can exhibit a variety of biological activities, including anti-inflammatory, antibacterial, and antiviral properties, making them significant in drug discovery.
  • Stereochemistry: The specific stereochemical annotations (i.e., S and R configurations) highlight the chiral centers present in the molecule, emphasizing the importance of stereochemistry in biological systems and drug efficacy.
  • Functional Groups: The presence of multiple hydroxyl (-OH) groups in its structure suggests that this compound could engage in hydrogen bonding, influencing its reactivity and interactions with biomolecules.
  • Challenging Synthesis: The synthesis of such intricate organic molecules often presents numerous challenges, including the need for precise control over stereochemistry and the selection of appropriate synthetic pathways.

In summary, compounds with such complex structures not only fascinate chemists due to their intricate design but also serve crucial roles in biological processes, making their study essential for both fundamental chemistry and applied sciences.

"The beauty of chemistry lies in its complexity and the potential to explore the unknown."

Synonyms
NS00093824