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Digitoxigenin

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Identification
Molecular formula
C23H34O4
CAS number
143-62-4
IUPAC name
(5S,10S,13R,14S,17R)-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]phenanthrene-10-carbaldehyde
State
State

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

Melting point (Celsius)
236.00
Melting point (Kelvin)
509.15
Boiling point (Celsius)
285.00
Boiling point (Kelvin)
558.15
General information
Molecular weight
402.54g/mol
Molar mass
402.5360g/mol
Density
1.3000g/cm3
Appearence

Digitoxigenin is typically a white, crystalline solid. It is known to form needle-like crystals.

Comment on solubility

Solubility Characteristics

The solubility of the compound (5S,10S,13R,14S,17R)-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]phenanthrene-10-carbaldehyde is influenced by various structural factors:

  • Polarity: With multiple hydroxyl (-OH) groups present, the compound exhibits a relatively high polarity. This fact generally enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The numerous hydroxyl groups can form hydrogen bonds with solvent molecules, further increasing solubility.
  • Hydrophobic Regions: However, the presence of larger hydrophobic hydrocarbon sections may limit solubility in purely polar solvents. Hence, organic solvents may be better suited for dissolution.
  • Temperature Dependency: As with many compounds, increasing temperature may enhance solubility due to greater molecular motion, aiding dissolution.

In conclusion, while the compound can be said to be relatively soluble in polar solvents due to its functional groups, the hydrophobic portions may pose challenges for solubility in very polar environments. As such, one might reflect on the phrase: "Solubility is a dance between polarity and structure."

Interesting facts

Interesting Facts about (5S,10S,13R,14S,17R)-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]phenanthrene-10-carbaldehyde

This complex compound, notable for its intricate structure, belongs to the class of steroids and holds a special significance in both natural product chemistry and medicinal applications. The presence of multiple hydroxy groups and a unique oxopyran moiety adds to its biological properties, making it fascinating to chemists.

Key Features

  • Stereochemistry: The compound has multiple chiral centers, indicated by its extensive stereochemical descriptors (5S, 10S, 13R, etc.). This complexity provides insight into how molecular shape influences its biological activity.
  • Biological Relevance: Many steroid derivatives are known for their role in biochemical pathways. This compound may play a part in influencing hormonal activities or serve as a precursor for bioactive molecules.
  • Natural Origins: Compounds of this nature are often derived from natural sources, which can lead to discoveries of new therapeutic agents, especially in the realm of anti-cancer or anti-inflammatory drugs.
  • Delivery Mechanisms: The presence of tetrahydropyran and hydroxy groups suggests potential for improved solubility and pharmacokinetics in drug formulation.

Moreover, the aldehyde group at the end of the structure is particularly interesting; aldehydes are reactive and can participate in various chemical reactions, such as condensation and oxidation, which can be leveraged in organic synthesis and drug development.

This compound serves as a striking example of how complex molecular architectures can lead to profound implications in health and disease, challenging students and researchers alike to delve deeper into the world of organic chemistry.

Synonyms
DTXSID30965279
5-(Hexopyranosyloxy)-14-hydroxy-19-oxobufa-3,20,22-trienolide