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Cardenolide

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Identification
Molecular formula
C29H44O9
CAS number
NA
IUPAC name
4-[(1R,3S,5S,10R,13R,14S)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5R)-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]phenanthren-17-yl]tetrahydrofuran-2-one
State
State

The compound is generally in a solid state at room temperature. It can dissolve in organic solvents, and its stable solid form is often used in laboratories for various types of chemical analyses.

Melting point (Celsius)
232.00
Melting point (Kelvin)
505.15
Boiling point (Celsius)
396.00
Boiling point (Kelvin)
669.15
General information
Molecular weight
548.65g/mol
Molar mass
548.6500g/mol
Density
1.2300g/cm3
Appearence

The compound is typically a white crystalline solid that may exhibit some optical activity due to its chiral centers. The appearance as a solid or crystalline form can vary between having a shiny surface or being matte depending on its purity and processing.

Comment on solubility

Solubility of 4-[(1R,3S,5S,10R,13R,14S)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5R)-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]phenanthren-17-yl]tetrahydrofuran-2-one

The solubility of this complex organic compound is influenced by several factors, primarily due to its intricate structural features. Here are some key points regarding its solubility:

  • Polarity: The presence of multiple hydroxyl groups in the structure suggests a high degree of polarity, which typically enhances solubility in polar solvents such as water and alcohol.
  • Hydrophobic Regions: However, the dodecahydro and cyclopentaphenanthrene portions of the molecule may introduce hydrophobic characteristics, which could limit its solubility in strictly polar environments.
  • Saturation Levels: The extent of saturation of the carbon rings and the number of substituents can greatly affect solubility; saturated portions generally favor dissolved states in organic solvents.
  • Temperature Dependency: Like many compounds, solubility may vary with temperature. Generally, increasing the temperature can increase solubility, especially for solids.

In conclusion, while the presence of hydroxyl groups typically promotes solubility, the overall hydrophobic character and complex structure of the compound may lead to a nuanced solubility profile. Therefore, it's essential to consider the solvent's properties when predicting how this compound will behave in various environments. Understanding these interactions could be pivotal for potential applications in pharmaceuticals and materials science.

Interesting facts

Interesting Facts about 4-[(1R,3S,5S,10R,13R,14S)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5R)-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]phenanthren-17-yl]tetrahydrofuran-2-one

This complex compound is a noteworthy example of a natural product with significant biological implications. Its intricate molecular structure showcases the beauty of organic synthesis, featuring multiple hydroxyl groups and stereogenic centers that highlight the compound's stereochemistry. Here are some fascinating details:

  • Natural Source: This compound may be derived from plants, particularly those known for their medicinal properties, reflecting the intricate relationship between chemistry and nature.
  • Biological Activity: Many compounds with similar structures have been studied for their potential health benefits, including anti-inflammatory and antioxidant effects. Research into this compound could reveal similar therapeutic properties.
  • Complexity: The multi-ring structure and various functional groups contribute to a dynamic chemical behavior, making it a subject of interest for chemists exploring reaction mechanisms and interaction with biological systems.
  • Stereochemistry: The specific arrangement of atoms in this compound plays a crucial role in its reactivity and interactions, making enantiomeric forms potentially significant in pharmacological contexts.
  • Research Potential: Ongoing research might focus on its synthesis, potential drug applications, or role within its natural ecosystem, providing ample opportunities for discovery and innovation in applied chemistry.

In the words of renowned chemist Linus Pauling, "The best way to have a good idea is to have lots of ideas." This compound exemplifies the excitement of chemical discovery, reminding us of the endless possibilities that originate from understanding the molecular world.

Synonyms
Dihydroouabin
Dihydro-g-strophathin
DIHYDROOUABAIN
Ouabain, dihydro-
EINECS 214-663-0
BRN 0071786
DTXSID60922658
4-18-00-03552 (Beilstein Handbook Reference)
1183-35-3
5-beta-20-xi-Cardanolide, 3-beta-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1-beta,5,11-alpha,14,19-pentahydroxy-
CHEBI:131146
(1beta,3beta,5beta,11alpha,20xi)-3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,5,11,14,19-pentahydroxycardanolide
(1beta,3beta,5beta,11alpha,20xi)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycardanolide
(20xi)-3beta-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1beta,5,11alpha,14,19-pentahydroxy-5beta-cardanolide
(20xi)-3beta-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1beta,5,11alpha,14,19-pentahydroxy-5beta-cardanolide
3beta-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1beta,5,11alpha,14,19-pentahydroxy-5beta,20xi-cardanolide
3beta-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1beta,5,11alpha,14,19-pentahydroxy-5beta,20xi-cardanolide
dihydro-g-strophanthin
Ouabain, dihydro-(7CI)
DTXCID801351537
(20xi)-3beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1beta,5beta,11alpha,14,19-pentahydroxycardanolide
4-[(1R,3S,5S,10R,13R,14S)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5R)-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]phenanthren-17-yl]oxolan-2-one