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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-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

Digoxin is typically a solid at room temperature, existing in a crystalline powder form.

Melting point (Celsius)
230.00
Melting point (Kelvin)
503.15
Boiling point (Celsius)
273.99
Boiling point (Kelvin)
547.14
General information
Molecular weight
780.94g/mol
Molar mass
780.9440g/mol
Density
1.2900g/cm3
Appearence

Digoxin appears as a white, odorless crystalline powder. It is sparingly soluble in water and freely soluble in solutions of sodium hydroxide.

Comment on solubility

Solubility of 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Understanding the solubility of this complex compound demands consideration of several factors due to its intricate structure:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the compound likely exhibits significant polar characteristics, which can enhance its solubility in polar solvents like water.
  • Size and Structure: Its large, polycyclic structure may hinder solubility in certain solvents, particularly non-polar organic solvents, leading to solubility challenges.
  • Hydrophilic vs. Hydrophobic: The balance between hydrophilic (water-attracting) and hydrophobic (water-repelling) regions plays a critical role; while the -OH groups are hydrophilic, the bulky hydrocarbon portions may impact overall solubility.
  • Solvent Compatibility: This compound might show varying solubility in organic solvents such as ethanol or acetone, which may serve as good solvents due to their polarity.

In general, “the solubility of organic compounds is often complex and influenced by their functional groups, structure, and the nature of the solvent,” making empirical testing essential for accurate determination.

To summarize, the solubility of this compound is expected to be moderate to high in polar solvents while potentially decreasing in non-polar settings, necessitating careful evaluation according to the solvent choice.

Interesting facts

Interesting Facts about 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

This fascinating compound is an organic molecule classified as a steroid and is notable for its complex structure and biological significance. Here are some intriguing aspects to consider:

  • Steroidal Backbone: The compound boasts a steroidal core, which is a structural hallmark associated with various hormones, including testosterone and estrogen. Its intricate arrangement contributes to its potential biological activity.
  • Natural Variants: Compounds with similar structures can be derived from natural sources. Steroids are widely found in plants and animals, playing crucial roles in physiological processes.
  • Potential Bioactivity: The presence of multiple hydroxy groups suggests that it may exhibit significant interaction with biological systems, potentially influencing metabolic pathways or acting as a signaling molecule.
  • Research Interest: Scientists are keenly interested in studying this compound due to its possible implications in pharmacology and medicinal chemistry, particularly in the development of novel therapeutic agents.
  • Structural Complexity: The detailed stereochemistry, indicated by the several stereocenters in its name, presents a challenge in synthesis, making it a subject of interest in synthetic organic chemistry.

In summary, 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one is a compound whose exploration may yield important insights into both fundamental research and practical application. Its unique features make it a notable subject for chemists and biologists alike.

Synonyms
Periplogenin
514-39-6
Desoxostrophanthidin
5-beta-Hydroxydigitoxigenin
5.beta.-Hydroxydigitoxigenin
UNII-B6808P7IY9
3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
B6808P7IY9
PERIPLOGENIN [MI]
3-beta,5,14-Trihydroxy-5-beta-card-20(22)-enolide
5-beta-CARD-20(22)-ENOLIDE, 3-beta,5,14-TRIHYDROXY-
Card-20(22)-enolide, 3,5,14-trihydroxy-, (3-beta,5-beta)-
Card-20(22)-enolide, 3,5,14-trihydroxy-, (3.beta.,5.beta.)-
3.beta.,5.beta.,14.beta.-Trihydroxy-20(22)-cardenolide
5.beta.-Card-20(22)-enolide, 3.beta.,5,14-trihydroxy-
(3.BETA.,5.BETA.)-3,5,14-TRIHYDROXYCARD-20(22)-ENOLIDE
3-((3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-17-yl)-2H-furan-5-one
5beta-Hydroxydigitoxigenin
3beta,5beta,14beta-Trihydroxy-20(22)-cardenolide
5beta-Card-20(22)-enolide, 3beta,5,14-trihydroxy-
(3beta,5beta)-3,5,14-trihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3,5,14-trihydroxy-, (3beta,5beta)-
Card-20(22)-enolide, 3,5,14-trihydroxy-, (3-beta,5-beta)-(9CI)
qjpckajtlhdncs-fbaxfmhrsa-n
MFCD01745139
CHEMBL460768
SCHEMBL1483841
DTXSID50965711
HY-N2414
MSK174296
s9168
AKOS015897157
CCG-268535
AC-34247
DA-56703
FP167441
MS-26510
3,5,14-Trihydroxycard-20(22)-enolide
1ST174296
3,5,14-Trihydroxycard-20(22)-enolide #
CS-0022615
NS00093752
Q27274425