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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
State
State

At room temperature, digoxin exists as a solid. It is usually handled in powdered form for its use in various pharmaceutical applications.

Melting point (Celsius)
249.00
Melting point (Kelvin)
522.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
780.94g/mol
Molar mass
780.9380g/mol
Density
1.2800g/cm3
Appearence

Digoxin appears as a crystalline white powder with no noticeable odor. It is relatively stable in air if kept dry, but can degrade upon exposure to light.

Comment on solubility

Solubility of 3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The solubility of the compound 3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one can be influenced by several factors:

  • Polarity: The presence of multiple hydroxyl (-OH) groups enhances its polarity, which typically increases solubility in polar solvents.
  • Hydrogen Bonding: The hydroxyl groups can form hydrogen bonds with water, further improving solubility in aqueous solutions.
  • Structural Complexity: Its complex structure may lead to variable solubility depending on the environment and solvent.
  • Concentration: At certain concentrations, it may exhibit unique solubility characteristics that could deviate from expected patterns.

Due to these intricacies, it is crucial to conduct empirical testing to determine its solubility in specific solvents. As with many complex organic compounds, solubility can be a critical factor impacting its biological activity and applications in various fields.

Interesting facts

Interesting Facts about 3-[(3S,5R,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

This compound belongs to a fascinating category of natural products known as steroids. Steroids play essential roles in biology and medicine, and this specific compound is notable for its complex structure and specific stereochemistry.

Key Highlights:

  • Natural Origin: This compound is derived from natural substances and might be found in various plant sources, which are often utilized in traditional medicine.
  • Pharmacological Potential: Many similar compounds exhibit biological activities such as anti-inflammatory and anticancer effects, suggesting potential therapeutic applications.
  • Stereochemistry Significance: The specific arrangement of atoms in this molecule, characterized by multiple chiral centers, leads to unique chemical properties and biological interactions.
  • Research Interest: Scientists are increasingly interested in compounds with intricate structures like this one for drug development, leading to a deeper understanding of molecular interactions.
  • Versatile Functional Groups: The presence of functional groups, such as the furan and hydroxyl groups, contributes to the compound's reactivity and solubility profiles, making it an intriguing subject for chemists.

Working with such a complex molecular structure offers both challenges and rewards. As in the words of renowned chemist Linus Pauling, "The best way to have a good idea is to have lots of ideas." This sentiment rings true in the realm of steroid chemistry, where innovative approaches can lead to groundbreaking therapeutic agents.

Studying compounds like this one not only enriches our understanding of organic and medicinal chemistry but also illuminates their roles in biological systems and their potential for developing new drugs. The journey of discovery in the field of chemistry is as exciting as it is vital!

Synonyms
Digitoxigenin digitoxoside
R83CK7MGW3
EINECS 242-284-0
BRN 0066592
(5beta)-3beta-((2,6-Dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide
UNII-R83CK7MGW3
3-((2,6-Dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide (3beta,5beta)-
3-beta-O-(2,6-Dideoxy-beta-D-ribo-hexopyranosyl)-14-hydroxy-5-beta-card-20(22)-enolide
4-18-00-01475 (Beilstein Handbook Reference)
DTXSID50939790
5-beta-Card-20(22)-enolide, 3-beta-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-14-hydroxy-
3-[(2,6-Dideoxyhexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide