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Digitoxigenin

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Identification
Molecular formula
C23H34O4
CAS number
143-62-4
IUPAC name
[(3S,5R,10S,13R,14S,16S,17R)-16-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] formate
State
State

At room temperature, digitoxigenin is in a solid state, manifesting as a powder or crystalline form.

Melting point (Celsius)
245.00
Melting point (Kelvin)
518.15
Boiling point (Celsius)
524.10
Boiling point (Kelvin)
797.30
General information
Molecular weight
414.56g/mol
Molar mass
414.5620g/mol
Density
1.2800g/cm3
Appearence

Digitoxigenin appears as a white crystalline powder. It may also occur as colorless crystals depending on the source and conditions of observation.

Comment on solubility

Solubility of [(3S,5R,10S,13R,14S,16S,17R)-16-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] formate

The solubility of this complex organic compound can be influenced by several factors, including its molecular structure, functional groups, and polarity. Key considerations regarding the solubility include:

  • Polarity: The presence of polar functional groups, such as hydroxyls and carbonyls, can enhance solubility in polar solvents like water.
  • Hydrophobic regions: The large hydrophobic hydrocarbon portions of the molecule may lead to greater solubility in non-polar solvents, which could include oils or organic solvents.
  • Hydrogen bonding: The potential for hydrogen bonding can significantly affect solubility, often increasing it in polar environments.

In general, the solubility of this compound will likely be:

  • Low in water due to the expansive non-polar sections.
  • Higher in organic solvents such as ethanol or acetone where it can better interact with similar hydrophobic compounds.

As a result, it is crucial to consider the context in which this compound will be used to accurately predict its solubility properties. The specific solubility behavior can provide insights into its potential applications and interactions in various environments.

Interesting facts

Interesting Facts about the Compound

This remarkable compound, with its intricate structure, belongs to a class of molecules known for their diverse biological activities. Its complexity not only piques the interest of chemists but also opens the door to various potential applications in medicinal chemistry and pharmacology.

Biological Significance

1. Potential Therapeutic Applications: Compounds similar to this one have been studied for their potential in treating various diseases, including cancer and hormonal imbalances. The specific functionalities of the formyloxy and hydroxy groups can play crucial roles in biological interactions.

2. Natural Sources: Many compounds with such structures are often derived from natural products or serve as analogs to plant-derived substances known for their medicinal properties.

Structural Highlights

The compound's configuration features multiple stereogenic centers, which may confer unique spatial properties that affect biological activity:

  • Complex Stereochemistry: The specific arrangement of atoms can significantly impact the compound's reactivity and interaction with biological targets.
  • Cyclic Structure: The incorporation of a cyclopentaphenanthrene structure adds rigidity and stability, potentially influencing its binding affinity in biological systems.

Research Insights

Researchers are continuously exploring the structure-activity relationship (SAR) of such compounds to optimize their efficacy while minimizing side effects. This process involves:

  • Modifying functional groups to enhance biological activity.
  • Studying how small changes in structure can lead to significant differences in behavior in biological assays.

Conclusion

With ongoing research and interest in complex organic structures like this compound, it represents a fascinating intersection of chemistry and biology. Its potential to contribute to drug development makes it a significant focus for scientists eager to unlock the mysteries of nature’s chemistry.

Synonyms
3-Formyl-gitaloxigenin
1256-58-2
3-16-Formyl-gitoxigenin
BRN 0062377
3-Formylgitaloxigenin
3-beta,14,16-beta-Trihydroxy-5-beta-card-20(22)-enolide 3,16-diformate
5-beta-CARD-20(22)-ENOLIDE, 3-beta,14,16-beta-TRIHYDROXY-, 3,16-DIFORMATE
Card-20(22)-enolide, 3,16-bis(formyloxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-
DTXSID00925183
3,16-Bis(formyloxy)-14-hydroxycard-20(22)-enolide