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Digitoxigenin

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Identification
Molecular formula
C23H34O5
CAS number
143-62-4
IUPAC name
(3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,5S)-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]phenanthrene-10-carbaldehyde
State
State

Digitoxigenin is typically found as a solid at room temperature.

Melting point (Celsius)
249.00
Melting point (Kelvin)
522.15
Boiling point (Celsius)
542.15
Boiling point (Kelvin)
815.30
General information
Molecular weight
387.49g/mol
Molar mass
387.4930g/mol
Density
1.2700g/cm3
Appearence

Digitoxigenin appears as a white crystalline solid. It is sparingly soluble in water and soluble in organic solvents such as alcohols.

Comment on solubility

Solubility Characteristics

The compound (3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,5S)-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]phenanthrene-10-carbaldehyde exhibits unique solubility properties due to its complex molecular structure. Understanding its solubility is essential for applications in both research and industry.

Factors Influencing Solubility

Several factors can influence the solubility of this compound:

  • Molecular Polarity: The presence of multiple hydroxyl groups suggests higher polarity, potentially increasing solubility in polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvents could enhance solubility in water and alcohols.
  • Alkyl Chain Length: The large nonpolar regions may hinder solubility in non-polar solvents.
  • Temperature: Generally, increasing temperature can improve the solubility of many organic compounds.

Expected Solubility

Given its structure, one might expect:

  • Higher Solubility in Water: Due to the multiple hydroxyl (-OH) groups.
  • Moderate Solubility in Organic Solvents: Potentially soluble in alcohols and dimethyl sulfoxide (DMSO), with limited solubility in non-polar solvents.

In conclusion, while specific solubility data may not be readily available for this compound, its structural characteristics suggest that it is likely to be more soluble in polar solvents than in non-polar ones due to the strong influence of functional groups present in the molecule.

Interesting facts

Interesting Facts about (3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,5S)-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]phenanthrene-10-carbaldehyde

This complex organic compound belongs to a class of molecules known for their intricate structures and diverse biological activities. Here are some noteworthy aspects of this compound:

  • Natural Product Synthesis: Many compounds with similar structural features are often isolated from natural sources, particularly plants. Their isolation and synthesis involve advanced organic chemistry techniques.
  • Biological Activity: Compounds of this type frequently exhibit significant biological properties, such as antitumor, anti-inflammatory, or antimicrobial activities, which make them subjects of interest in pharmaceutical research.
  • Stereochemistry: The detailed stereochemistry, indicated by the (S) and (R) notations, plays a critical role in determining the compound's activity and interactions in biological systems. Stereoisomers can have profoundly different effects in medicinal applications.
  • Functional Groups: The presence of multiple hydroxyl groups (-OH) and a furan ring in its structure can contribute to various chemical reactivities, enhancing its potential function in different chemical reactions.
  • Research Relevance: Scientists are conducting ongoing research to explore the potential applications of this type of compound in drug development and as therapeutic agents.

In conclusion, the intricate design and potential utility of this compound exemplify the endless possibilities within organic chemistry. As we delve deeper into its properties and effects, we stand on the brink of discovering new therapeutic avenues that can benefit humanity. As the famous chemist Linus Pauling once said, "The best way to have a good idea is to have lots of ideas." This compound certainly adds to the wealth of ideas waiting to be explored.

Synonyms
Cheirotoxin, degluco-
Strophanthidin 6-deoxyglucoside
5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-beta-glucopyranosyl)oxy)-5,14-dihydroxy-19-oxo-
Card-20(22)-enolide, 3-((6-deoxy-beta-D-gulopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5beta)-
Cheirotoxin, degluco-(7CI)
5822-57-1
Deglucocheirotoxin
Strophalloside
4336-94-1
(3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
3-beta-((6-Deoxy-beta-D-allopyranosyl)oxy)-5-beta,14-dihydroxy-19-oxocard-20(22)-enolide
Card-20(22)-enolide, 3-((6-deoxy-beta-D-allopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3-beta,5-beta)-