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Ouabain

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Identification
Molecular formula
C29H44O12
CAS number
630-60-4
IUPAC name
3-[(3S,5S,10R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,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]phenanthren-17-yl]-2H-furan-5-one
State
State

Solid: Ouabain is a solid at room temperature, generally found in a crystalline form.

Melting point (Celsius)
221.00
Melting point (Kelvin)
494.15
Boiling point (Celsius)
275.00
Boiling point (Kelvin)
548.15
General information
Molecular weight
584.66g/mol
Molar mass
584.6620g/mol
Density
0.7900g/cm3
Appearence

Ouabain typically appears as a white crystalline solid.

Comment on solubility

Solubility of 3-[(3S,5S,10R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,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]phenanthren-17-yl]-2H-furan-5-one

The solubility of this compound is influenced by several factors, largely due to its complex molecular structure. The presence of multiple hydroxy groups greatly affects its behavior in different solvents. Here are some key points regarding its solubility:

  • Polarity: The numerous hydroxyl (-OH) functional groups are highly polar, which typically enhances solubility in polar solvents such as water.
  • Hydrogen bonding: This compound's ability to form hydrogen bonds also increases its potential for solubility in aqueous environments.
  • Solvent compatibility: It is likely to be soluble in alcohols and other moderately polar organic solvents, while being less soluble in non-polar solvents.
  • Concentration effects: High concentrations of the compound may lead to precipitation, especially if the solvent cannot accommodate the solute's interactions.

As with many organic compounds, the “like dissolves like” principle holds significant weight in predicting solubility behaviors. Therefore, this compound may present interesting challenges in solubility depending on the solvent system utilized. Understanding these nuances is crucial for applications in pharmaceuticals and chemical synthesis.

Interesting facts

Interesting Facts about 3-[(3S,5S,10R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,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]phenanthren-17-yl]-2H-furan-5-one

This complex compound belongs to the class of natural products known as triterpenes, which are known for their diverse biological activities and implications in medicinal chemistry. The intricate structure showcases a variety of functional groups, making it a potential candidate for biological activity in various avenues of therapeutic research.

Key Features:

  • Stereochemistry: The presence of multiple chiral centers within the molecule lends it unique stereochemical properties that may influence its interaction with biological systems.
  • Hydroxyl Motifs: The compound features several hydroxyl groups, which are known to enhance solubility and can significantly impact the compound’s activity in biological systems.
  • Tetracyclic Framework: The core tetracyclic structure is characteristic of many sterols and steroid derivatives, commonly associated with hormonal functions and cell signaling.

Moreover, it is intriguing to consider the compound's potential applications in pharmacology:

  • **Antioxidant activity**: Natural products like this compound often exhibit diverse mechanisms that can combat oxidative stress.
  • **Anti-inflammatory properties**: Many compounds with similar frameworks show promise in reducing inflammation, which is beneficial for various chronic diseases.
  • **Antimicrobial properties**: Biological assays can reveal whether this compound helps inhibit bacterial and fungal growth, opening up pathways to new antibiotics.

As the field of chemistry advances, the exploration of such complex natural compounds continues to be a source of inspiration for scientists looking to develop new therapeutics. The intricacy of the molecular design not only challenges chemists in terms of synthesis but also sparks intrigue regarding the biological roles these compounds play in nature.

"Nature does not hurry, yet everything is accomplished." – Lao Tzu

This quote encapsulates the essence of exploring natural compounds, where patience in research can lead to groundbreaking discoveries that have the potential to enhance human health and wellbeing.

Synonyms
Sarhamnolosid [German]
Sarhamnolosid
Sarmentologenin-L-rhamnosid
Sarmentologenin-L-rhamnosid [German]
6891-94-7
3-beta-((L-Rhamnopyranosyl)oxy)-5,11,14,19-tetrahydroxy-5-beta-card-20(22)-enolide
5-beta-Card-20(22)-enolide, 3-beta-((L-rhamnopyranosyl)oxy)-5,11,14,19-tetrahydroxy-
DTXSID90988621
3-[(6-Deoxyhexopyranosyl)oxy]-5,11,14,19-tetrahydroxycard-20(22)-enolide