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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
State
State

Digitoxin is typically a solid at room temperature. It is not very soluble in water, but soluble in organic solvents like chloroform and ethanol.

Melting point (Celsius)
250.00
Melting point (Kelvin)
523.00
Boiling point (Celsius)
275.00
Boiling point (Kelvin)
548.00
General information
Molecular weight
764.94g/mol
Molar mass
764.9390g/mol
Density
1.1000g/cm3
Appearence

Digitoxin typically appears as a white crystalline powder. It is odorless and has a bitter taste. As with many other chemical compounds, the appearance might vary slightly when under different conditions or when impurities are present.

Comment on solubility

Solubility Insights

The solubility of the compound (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde, with the chemical formula C41H64O13, raises interesting questions about its solubility characteristics. Given the complex structure, which includes multiple hydroxyl groups, one can infer certain solubility behaviors:

  • The presence of hydroxyl (-OH) groups typically enhances solubility in polar solvents, such as water, due to their ability to form hydrogen bonds.
  • However, the large hydrocarbon framework indicated by the long chain may contribute to a hydrophobic character, reducing overall solubility in polar solvents.
  • Solubility in organic solvents is also a factor to consider, as compounds with large hydrophobic regions may dissolve more readily in non-polar solvents like hexane or dichloromethane.

In general, the solubility of such complex organic molecules is influenced by both their hydrophilic and hydrophobic regions which ultimately dictates their dissolving behavior. Therefore, while one might expect some solubility in aqueous environments owing to the hydroxyl groups, this may be counterbalanced by the extensive non-polar structures. In practice, determining the solubility would likely require empirical testing.

Interesting facts

Exploring (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

This complex organic compound belongs to a class of molecules known for their intriguing structural features and potential biological significance. Here are some fascinating aspects of this compound:

  • **Hydroxyl Groups**: With three hydroxyl (-OH) functional groups, this compound showcases the importance of hydroxylation in modulating the chemical reactivity and solubility of organic molecules. Hydroxyl groups can participate in hydrogen bonding, influencing the overall molecular interactions.
  • **Structural Complexity**: The compound's elaborate structure, characterized by multiple fused rings, is a reflection of natural products that often embody intricate architectures. This complexity raises interesting questions regarding its biosynthesis and the enzymes involved in its formation.
  • **Potential Biological Activity**: Compounds with similar structures have been studied for their biological activities, including anti-cancer and anti-inflammatory properties. This raises compelling research opportunities exploring the pharmacological potential of this molecule.
  • **Furan and Its Derivatives**: The presence of a furan ring highlights the importance of this functional group in organic chemistry. Furans are known to exhibit various biological effects and can be involved in chemical transformations that contribute to the reactivity of similar compounds.

In the words of the renowned chemist Linus Pauling, “The best way to have a good idea is to have a lot of ideas.” This compound stands as a testament to the endless possibilities that emerge from understanding complex organic structures and their interactions.

As researchers continue to investigate compounds like this one, the integration of molecular biology and synthetic chemistry could pave the way for innovative applications in pharmaceuticals and biotechnology.

Synonyms
strophanthidin
Convallatoxigenin
66-28-4
Strophanthidine
Corchsularin
k-Strophanthidin
Corchorgenin
Erysimupicrone
Corchorin
Corchoside A aglycon
Strophanthidin K
Erysimupikron
Apocymarin
Apocynamarin
k-Strophanthidine
Cymarigenin
Cynotoxin
5beta-Hydroxy-19-oxodigitoxigenin
Antibiotic XS-89
NSC-86078
Strophantidine
CHEBI:38178
3beta,5,14-Trihydroxy-19-oxo-5beta-card-20(22)-enolide
XS-89
5-beta-Hydroxy-19-oxodigitoxigenin
EINECS 200-626-6
NSC 86078
BRN 0097859
(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
STROPHANTHIN-K
W5O632DN33
NSC86078
STROPHANTHIDIN [MI]
MLS002153969
3-beta,5,14-Trioxy-19-oxo-digen-(20:22)-olid [German]
STROPHANTHIN-K [WHO-DD]
19-Oxo-cardogenen-(20:22)-triol-(3-beta,5,14) [German]
3-beta,5,14-Trihydroxy-19-oxo-5-beta-card-20(22)-enolide
3-beta,5,14-Trioxy-19-oxo-carden-(20:22)-olid [German]
(3beta,5beta)-3,5,14-Trihydroxy-19-oxocard-20(22)-enolide
DTXSID00903966
Card-20(22)-enolide, 3,5,14-trihydroxy-19-oxo-, (3beta,5beta)-
5-18-05-00126 (Beilstein Handbook Reference)
3-beta,5,14-Trioxy-19-oxo-carden-(20:22)-olid
3-beta,5,14-Trioxy-19-oxo-digen-(20:22)-olid
5.beta.-Hydroxy-19-oxodigitoxigenin
19-OXO-CARDOGENEN-(20:22)-TRIOL-(3-beta,5,14)
5beta-Card-20(22)-enolide, 3beta,5,14-trihydroxy-19-oxo-
(3.beta.,5.beta.)-3,5,14-Trihydroxy-19-oxocard-20(22)-enolide
5-beta-CARD-20(22)-ENOLIDE, 3-beta,5,14-TRIHYDROXY-19-OXO-
Card-20(22)-enolide, 3,5,14-trihydroxy-19-oxo-, (3-beta,5-beta)-
Cymarigenen
3beta,5,14-Trihydroxy-19-oxo-5beta,20(22)-cardenolide
CARD-20(22)-ENOLIDE, 3,5,14-TRIHYDROXY-19-OXO-
5.beta.-Card-20(22)-enolide, 3.beta.,5,14-trihydroxy-19-oxo-
UNII-W5O632DN33
(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthrene-10-carbaldehyde
Prestwick_117
kappa-Strophanthidine
MFCD00046266
Corchoside A, aglycon
Prestwick0_000710
Prestwick1_000710
Prestwick2_000710
Prestwick3_000710
Strophanthidin (Standard)
19-Oxo-cardogenen-(20:22)-triol-(3-.beta.,5,14)
3-.beta.,5,14-Trioxy-19-oxo-carden-(20:22)-olid
3-.beta.,5,14-Trioxy-19-oxo-digen-(20:22)-olid
BSPBio_000899
SCHEMBL240582
SPBio_002820
3.beta.,5,14-Trihydroxy-19-oxo-5.beta.-card-20(22)-enolide
BPBio1_000989
CHEMBL111743
Card-20(22)-enolide, 3,5,14-trihydroxy-19-oxo-, (3.beta.,5.beta.)-
ODJLBQGVINUMMR-HZXDTFASSA-N
DTXCID001331905
HMS1570M21
HMS2097M21
HMS2233O14
BDBM50255120
LMST01120005
AKOS024280415
HY-114252R
NCGC00142399-02
(1S,2S,5S,7S,11S,10R,14R,15R)-5,7,11-trihydroxy-15-methyl-14-(5-oxo(3-2-hydrof uryl))tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadecane-2-carbaldehyde
1397-98-4
NCI60_041903
SMR001233308
HY-114252
CS-0080731
NS00010436
C19988
F82324
SR-01000838893
Q1718068
SR-01000838893-2
BRD-K84595254-001-03-0
BRD-K84595254-001-10-5
5.beta.-Card-20(22)-enolide,5,14-trihydroxy-19-oxo-
WLN: L E5 B666TJ AVH E1 IQ MQ OQ F- DT5OV EHJ
3.beta.,14-Trihydroxy-19-oxo-5.beta.-card-20(22)-enolide
5beta-Card-20(22)-enolide, 3beta,5,14-trihydroxy-19-oxo-(8CI)
Card-20(22)-enolide,5,14-trihydroxy-19-oxo-, (3.beta.,5.beta.)-
Card-20(22)-enolide, 3,5,14-trihydroxy-19-oxo-, (3-beta,5-beta)-(9CI)