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Cardenolide

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Identification
Molecular formula
C29H44O6
CAS number
77-58-7
IUPAC name
3-[(3S,5S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,5R)-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]phenanthren-17-yl]-2H-furan-5-one
State
State

At room temperature, cardenolides are typically in a solid state, appearing as crystalline powders or solids.

Melting point (Celsius)
235.00
Melting point (Kelvin)
508.15
Boiling point (Celsius)
100.00
Boiling point (Kelvin)
373.15
General information
Molecular weight
480.59g/mol
Molar mass
480.5940g/mol
Density
1.2130g/cm3
Appearence

Cardenolides are typically white to off-white crystalline powders. They are often characterized by their glossy sheen and can appear as shiny translucent or opaque crystals depending on the specific environment in which they are crystallized.

Comment on solubility

Solubility of 3-[(3S,5S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,5R)-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]phenanthren-17-yl]-2H-furan-5-one

The solubility of 3-[(3S,5S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,5R)-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]phenanthren-17-yl]-2H-furan-5-one can be influenced by several factors due to its complex structure:

  • Hydroxyl Groups: The presence of multiple hydroxyl (–OH) groups typically enhances solubility in polar solvents. Each hydroxyl group contributes to hydrogen bonding, which can lead to improved solubility in water and alcohols.
  • Hydrophobic Regions: Conversely, the molecule contains considerable hydrophobic (non-polar) portions, which may hinder solubility in purely polar solvents, creating *competing interactions*.
  • Steric Effects: The three-dimensional arrangement of atoms due to the numerous chiral centers might impact how the molecule interacts with solvents, potentially resulting in steric hindrance that affects solubility.
  • Solvent Choice: Based on its structure, this compound may exhibit variable solubility profiles depending on the choice of solvent. It may dissolve well in certain organic solvents like dimethyl sulfoxide (DMSO) or ethanol, while demonstrating limited solubility in hexane or other non-polar solvents.

In summary, the solubility of this compound can be quite *context-dependent*, with a tendency to be soluble in polar environments due to its hydroxyl groups, while retaining challenges in hydrophobic surroundings due to its intricate molecular architecture. Factors such as solvent type, temperature, and concentration can play crucial roles in determining its overall solubility characteristics.

Interesting facts

Interesting Facts about 3-[(3S,5S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,5R)-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]phenanthren-17-yl]-2H-furan-5-one

This compound is a fascinating example of the complexity that can arise in organic chemistry, showcasing how intricate molecular structures can have significant biological implications. Here are some intriguing facts about this trihydroxy compound:

  • Natural Product Origins: This compound is often associated with natural products, which are compounds produced by living organisms. Many of these molecules exhibit potent biological activity.
  • Structural Diversity: The structural elements of this compound, including its multiple hydroxyl groups and a complex ring structure, contribute to its potential for engaging with biological targets, making it an interesting subject for pharmacological research.
  • Potential Therapeutic Uses: Compounds with such intricate polyhydroxy structures often have roles in medicine, including applications as antioxidants, anti-inflammatory agents, and even as anticancer drugs.
  • Biochemical Importance: Understanding the interactions of such compounds with enzymes and receptors can provide insights into drug design and the development of therapeutics.
  • Synthesis Challenges: The synthesis of such complex molecules poses significant challenges in organic chemistry, often requiring multiple steps and specific conditions to ensure the correct stereochemistry.
  • Research Applications: Compounds like this often serve as lead compounds in drug discovery, where structural modifications are made to enhance activity and selectivity for biological targets.

Furthermore, the presence of multiple hydroxy groups in its structure suggests that this compound may engage in hydrogen bonding, which can affect its solubility and interaction with other biological molecules. As researchers continue to explore complex organic compounds such as this one, they unlock potential avenues for innovation in therapeutic strategies.

Synonyms
Bipindosid [German]
Bipindosid
Bipindogenin-L-talomethylosid [German]
Bipindogenin-L-talomethylosid
3-beta-((6-Deoxy-L-talopyranosyl)oxy)-5,11-alpha,14-trihydroxy-5-beta-card-20(22)-enolide
5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-L-talopyranosyl)oxy)-5,11-alpha,14-trihydroxy-