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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
[(5S,10S,13R,14S,16S,17R)-10-formyl-14-hydroxy-13-methyl-17-(6-oxopyran-3-yl)-5-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
State
State

At room temperature, digitoxin exists as a solid.

Melting point (Celsius)
248.00
Melting point (Kelvin)
521.15
Boiling point (Celsius)
700.00
Boiling point (Kelvin)
973.15
General information
Molecular weight
764.94g/mol
Molar mass
764.9360g/mol
Density
1.2150g/cm3
Appearence

Digitoxin is typically found as a white, crystalline powder. It is devoid of any significant smell and has a slightly bitter taste.

Comment on solubility

Solubility of the Compound

The compound [(5S,10S,13R,14S,16S,17R)-10-formyl-14-hydroxy-13-methyl-17-(6-oxopyran-3-yl)-5-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate (C41H64O13) is a complex organic molecule with multiple functional groups that influence its solubility characteristics. Below are some key points regarding its solubility:

  • Polar Functional Groups: The presence of hydroxyl (-OH) and carbonyl (C=O) groups suggests that the compound may have good solubility in polar solvents such as water and alcohols.
  • Hydrophobic Regions: The large hydrophobic cyclopenta[a]phenanthren moiety in the structure indicates that the compound may have limited solubility in highly polar solvents, as hydrophobic interactions can dominate.
  • Solvent Selection: It is likely to dissolve better in solvents that provide a balance of polar and non-polar characteristics (e.g., ethanol, methanol).
  • Temperature Effects: Like many organic compounds, solubility could increase with temperature, suggesting that higher temperatures may enhance its dissolving process in relevant solvents.

In conclusion, while this compound is anticipated to exhibit moderate solubility in polar solvents, its solubility profile may be significantly affected by both the solvent composition and environmental conditions.

Interesting facts

Interesting Facts about the Compound

This fascinating compound, commonly known within certain scientific circles for its complex structure, showcases a remarkable interplay of functional groups and stereochemistry that makes it an intriguing subject of study.

Structural Insights

  • The compound features a unique *stereochemistry* denoted by its multiple stereocenters, which influence its biological activity and potential applications.
  • Its structure includes a *cyclopenta[a]phenanthrene* backbone, a configuration that is often found in natural products and can contribute to various pharmacological properties.
  • The presence of both a *formyl group* and multiple *hydroxyl groups* suggests a level of reactivity and potential for intermolecular interactions, which are vital in biological systems.

Biological Relevance

Compounds like this one are often investigated for their roles in biological systems:

  • They can act as *natural hormones* or derivatives thereof, signaling pathways that influence growth and development.
  • The complex makeup offers avenues for *therapeutic research*, particularly in oncology and endocrinology.
  • Studies show that similar compounds can exhibit significant effects in *cell signaling*, making them double as markers for various diseases.

Research Applications

Given its intricate structure and features, this compound is of particular interest in various research fields:

  • In *organic synthesis*, it provides an excellent example for the development of new methodologies to create complex molecules.
  • The compound serves as a model system for studying the effects of *stereochemistry* on chemical reactivity and biological activity.
  • Its versatility in modification allows chemists to probe the structure-activity relationship, essential in drug design.

The synthesis and modification of compounds like this can lead to *innovative pharmacological agents*. In summary, this complex compound reflects the beauty of chemical diversity and the potential for discovery in chemical research.

Synonyms
Scillicyanoside
Scillicyanosid [German]
Scillicyanosid
11005-49-5
[(5S,10S,13R,14S,16S,17R)-10-formyl-14-hydroxy-13-methyl-17-(6-oxopyran-3-yl)-5-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
BRN 0075059
4-18-00-03248 (Beilstein Handbook Reference)
5-beta,16-beta-Bufa-3,20,22-trienolide, 16-(acetyloxy)-5-(beta-D-glucopyranosyloxy)-14-hydroxy-19-oxo-
((5S,10S,13R,14S,16S,17R)-10-formyl-14-hydroxy-13-methyl-17-(6-oxopyran-3-yl)-5-((2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-16-yl) acetate
DTXSID90911474
16-(Acetyloxy)-5-(hexopyranosyloxy)-14-hydroxy-19-oxobufa-3,20,22-trienolide