Skip to main content

Digitoxigenin

ADVERTISEMENT
Identification
Molecular formula
C23H34O6
CAS number
143-62-4
IUPAC name
3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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

Digitoxigenin is a solid at room temperature, usually found as a crystalline powder.

Melting point (Celsius)
255.00
Melting point (Kelvin)
528.00
Boiling point (Celsius)
325.00
Boiling point (Kelvin)
598.00
General information
Molecular weight
402.51g/mol
Molar mass
402.5070g/mol
Density
1.1800g/cm3
Appearence

Digitoxigenin appears as a white crystalline powder. It is typically used as a reference compound in chemical research connected to cardiac glycosides.

Comment on solubility

Solubility of 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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 this complex organic compound can be characterized by several important factors:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the molecule may have polar characteristics, which can enhance its solubility in polar solvents such as water.
  • Hydrophobic regions: However, the extended hydrocarbon portions and the cyclopenta[a]phenanthrene structure indicate that there are also significant hydrophobic regions, potentially reducing solubility in aqueous environments.
  • Solvent compatibility: It is likely to be more soluble in organic solvents such as methanol, ethanol, or DMSO, owing to its structural features which favor interactions with these solvents.
  • Temperature dependence: Solubility can also vary with temperature; increasing temperature typically enhances solubility of organic compounds.

In conclusion, while the presence of hydroxyl groups suggests a degree of solubility in polar solvents, the overall structure and hydrophobic characteristics imply a more complex behavior. It is essential to consider both polar and non-polar interactions when predicting its solubility profile across different environments.

Interesting facts

Interesting Facts about 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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 complex organic molecule, known as a furan derivative, showcases the intricate beauty of Natural Product Chemistry. Here are some fascinating aspects of this compound:

  • Origin: This type of compound is often derived from various plant sources, showcasing nature's vast library of organic molecules utilized in traditional medicine.
  • Structural Complexity: The detailed stereochemistry of the compound includes multiple chiral centers, emphasizing the uniqueness of its 3D orientation which can greatly influence its biological activity.
  • Potential Applications: Compounds like this are of great interest in pharmaceutical chemistry, as their unique functional groups and stereochemical configurations may exhibit potent biological activities, including anti-inflammatory and anti-cancer properties.
  • Biological Interaction: The hydroxyl groups present in the structure may enhance solubility and interaction with biological systems, making this compound potential candidates for drug development.
  • Research Frontier: Due to its structural intricacies, it presents opportunities for chemists to explore new synthetic methodologies and understand biosynthetic pathways in plants.

As one dives into the details of such complex structures, they can appreciate the fine balance between natural beauty and the deep scientific inquiry, illustrating how each compound holds potential wonders just waiting to be discovered.


Synonyms
Periplogenin-D-glucosid [German]
18531-44-7
Periplogenin-beta-d-glucoside
Periplogenin-D-glucosid
5,14-Dihydroxy-3-beta-((D-glucopyranosyl)oxy)-5-beta-card-20(22)-enolide
5-beta-CARD-20(22)-ENOLIDE, 3-beta-((D-GLUCOPYRANOSYL)OXY)-5,14-DIHYDROXY-
DTXSID90939956
3-(Hexopyranosyloxy)-5,14-dihydroxycard-20(22)-enolide