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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-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
Digitoxin is a solid at room temperature. It is often used in a finely divided powder form for precise dosage and administration.
Melting point (Celsius)
268.00
Melting point (Kelvin)
541.15
Boiling point (Celsius)
252.40
Boiling point (Kelvin)
525.55
General information
Molecular weight
764.95g/mol
Molar mass
764.9510g/mol
Density
1.2980g/cm3
Appearence

Digitoxin appears as white crystals or crystalline powder. It is typically odorless or has a faint, characteristic odor. This compound is known for its bitter taste.

Comment on solubility

Solubility of 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-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 complex organic compounds such as this one can vary significantly based on structural components and environmental conditions. Here are some key points regarding its solubility:

  • Hydrophilicity vs. Hydrophobicity: The presence of multiple hydroxyl (–OH) groups suggests that the compound may exhibit hydrophilic characteristics, possibly enhancing solubility in polar solvents like water.

  • Polycyclic Structure: The intricate polycyclic framework can contribute to hydrophobic properties, potentially limiting solubility in non-polar solvents.

  • pH Dependence: Depending on the pH of the solution, the ionization of hydroxyl groups may affect solubility, with increased solubility in more basic or acidic conditions.

  • Temperature Effects: Like many organic compounds, solubility often increases with rising temperatures, which may allow for greater dissolution, particularly in solvents that can disrupt intermolecular interactions.

In conclusion, while predicting the exact solubility of this compound requires empirical testing, understanding these factors can provide a strong context for evaluating its solubility behavior in various environments.

Interesting facts

Interesting Facts about 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-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 complex compound, with its intricate structure, offers a fascinating glimpse into the world of organic chemistry and natural products. Known for being a natural product derivative, it is often discussed in the context of its biological activities and potential therapeutic benefits.

  • Biological Significance: This compound has garnered interest due to its potential pharmacological properties, making it a candidate for new medicinal compounds.
  • Stereochemistry: The stereocenters in its structure highlight the importance of chirality in medicinal chemistry. The specific configurations of the carbon atoms can influence the compound's biological activity greatly.
  • Synthetic Challenges: The synthesis of such a complex compound is a significant challenge in the field of organic synthesis, requiring advanced techniques and methodologies.
  • Natural Sources: Many compounds like this are typically derived from plants and may exhibit significant ecological roles, impacting various biological pathways.
  • Research Potential: Due to its structural complexity, researching this compound can uncover new methods applicable to drug discovery and development.

As one delves deeper into the chemistry of such compounds, one can appreciate the beauty in their design and the myriad possibilities they embody in advancing scientific knowledge. As Richard Feynman once said, "What I cannot create, I do not understand," capturing the essence of exploring complex structures that unlock new realms of understanding in science and medicine.

Synonyms
deslanoside
17598-65-1
Desacetyllanatoside C
Deacetyllanatoside C
Cedilanid-D
Deslanosido
Deslanosidum
glucodigoxin
Deacetylanatoside C
Desacetyl-Lanatoside C
YGY317RK75
DTXSID1022897
CHEBI:31468
Deslanatoside C
DTXCID302897
Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-O-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)-
Desacetyldigilanide C
Cedilanid D
(3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1->4)-O-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)-
Desacetyl Lanatoside
CedilanidD
3-[(O-beta-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide
Lanatoside, Desacetyl
(3beta,5beta,12beta)-3-((beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide
3-((O-beta-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide
C01AA07
241-568-1
3beta-(beta-D-Glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy)-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolide
3-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-((2R,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-6-methyl-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)oxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl)oxy-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
4-((1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-5-(((2R,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5S,6R)-4-hydroxy-6-methyl-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy)-6-methyloxan-2-yl)oxy)-6-methyloxan-2-yl)oxy)-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)-2,5-dihydrofuran-2-one
4-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-((2R,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-6-methyl-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)oxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-5H-furan-2-one
Deslanosid
MFCD00135818
Desace
Lanatoside C, deacetyl-
Sediranido
Lekozid
Deslanosidum C
Deslanosidum [INN-Latin]
Deslanosido [INN-Spanish]
Deacetyl-lanatoside C
Cedilanid-d (TN)
CAS-17598-65-1
EINECS 241-568-1
BRN 0078187
UNII-YGY317RK75
Cedilanide
Deslanoside [USP:INN:BAN:JAN]
NCGC00159441-02
Deacetyllanatoside C;Desacetyllanatoside C
Deslanoside (Standard)
DESLANOSIDE [MI]
DESLANOSIDE [INN]
DESLANOSIDE [JAN]
DESLANOSIDE [VANDF]
CHEMBL1614
DESLANOSIDE [MART.]
DESLANOSIDE [USP-RS]
DESLANOSIDE [WHO-DD]
3beta-(O-beta-D-Glucopyranosyl-(1-4)-O-beta-D-digitoxosyl-(1-4)-O-beta-D-digitoxosyl-(1-4)-beta-D-digitoxosyloxy-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolid
4-18-00-02455 (Beilstein Handbook Reference)
SCHEMBL125311
GTPL6806
orb1299144
Deslanoside (JP18/USP/INN)
HY-A0154R
DESLANOSIDE [ORANGE BOOK]
DESLANOSIDE [EP MONOGRAPH]
DESLANOSIDE [USP IMPURITY]
HY-A0154
MSK11160
Tox21_111671
AKOS040759327
Tox21_111671_1
DB01078
MD65946
NCGC00159441-03
3beta-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12beta,14-dihydroxy-5beta-card-20(22)-enolide
MS-31757
CS-0017480
NS00025778
D01240
E88575
EN300-23839400
Q5264583
BRD-K99919177-001-01-3
(3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
3-[(O-beta-D-glucopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide
CARD-20(22)-ENOLIDE, 3-((O-.BETA.-D-GLUCOPYRANOSYL-(1->4)-O-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-, (3.BETA.,5.BETA.,12.BETA.)-