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Cardenolide ouabain

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Identification
Molecular formula
C29H44O12
CAS number
11018-89-6
IUPAC name
[6-[6-[6-[[12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-2-methyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-4-yl] acetate
State
State

At room temperature, ouabain is typically found in a solid state, appearing as a crystalline powder. It is stable under normal conditions but should be stored in a dry, cool environment to maintain its stability and purity.

Melting point (Celsius)
212.00
Melting point (Kelvin)
485.15
Boiling point (Celsius)
267.00
Boiling point (Kelvin)
540.15
General information
Molecular weight
728.86g/mol
Molar mass
728.8550g/mol
Density
1.4530g/cm3
Appearence

Ouabain appears as a white crystalline solid. It is typically odorless and possesses a bitter taste. The compound is usually handled in a powdered form but may also be encountered as a prepared solution for laboratory uses. In its crystalline form, ouabain typically presents transparent or translucent crystalline structures.

Comment on solubility

Solubility of the Compound

The solubility of the compound with the name 6-[6-[6-[[12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-2-methyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-4-yl] acetate (C29H44O12) can vary significantly due to its complex structure and the presence of multiple functional groups.

Factors influencing its solubility include:

  • Presence of Hydroxyl Groups: The compound contains several hydroxyl (–OH) groups that can form hydrogen bonds with water, potentially enhancing solubility in polar solvents.
  • Hydrophobic Regions: Conversely, the large hydrophobic tetradecahydrocyclopenta[a]phenanthrene moiety may hinder solubility in aqueous environments.
  • Acetate Functional Group: The acetate group can contribute to compatibility with certain solvents and improve the overall solubility profile in organic solvents.

In summary, while the presence of multiple hydroxyl groups suggests that this compound may exhibit some solubility in polar solvents such as water, its larger hydrophobic portions may limit solubility overall. Thus, one can expect variable solubility depending on the solvent system employed.

Interesting facts

Interesting Facts About 6-Beta-Glucosyl-17-Acetoxy-12,14-Dihydroxy-10,13-Dimethyl-...

This compound is a fascinating example of a complex natural product that exhibits a rich structure and potential biological activity. Its unique characteristics arise from a variety of components, which can be broken down into notable facts:

  • Source: This compound is often derived from natural sources, particularly from plants, which are renowned for producing intricate organic compounds that serve various ecological functions.
  • Structure Complexity: With multiple hydroxyl groups and sugar moieties, this compound showcases a layered architecture that can influence its interactions and solubilization properties.
  • Biological Significance: Compounds with such complexities may demonstrate significant pharmacological properties, including anti-inflammatory, antioxidant, and anti-cancer activities, making them attractive candidates for medicinal research.
  • Enzymatic Interactions: The presence of functional groups like hydroxyls and the cyclic structures allows this compound to participate in various biochemical reactions, potentially acting as substrates or inhibitors in enzymatic pathways.
  • Potential Therapeutic Applications: Given its multifaceted structure, researchers are exploring its role in drug formulation, targeting pathways related to chronic illnesses and metabolic disorders.

This compound embodies the intricate relationships found within organic chemistry, where one molecule can encapsulate a wealth of potential applications and benefits in pharmaceuticals, providing scientists with ample opportunities for exploration and innovation.

Synonyms
Digilanide C
Celanide
Card-20(22)-enolide, 3-[(O-beta-D-glucopyranosyl-(1-->4)-O-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3beta,5beta,12beta)-
LANATOSIDE-C
NSC7533
Card-20(22)-enolide,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3.beta.,5.beta.,12.beta.)-
MLS002207214
CHEMBL110309
SCHEMBL18223891
DTXSID20860209
NSC119991
AKOS026750171
SMP1_000175
NCGC00166137-01
NCGC00166137-02
[6-[6-[6-[[12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-2-methyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
3-{[hexopyranosyl-(1->4)-3-o-acetyl-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
LS-15494
NCI60_041651
SMR001306767
DB-044235