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Digoxigenin

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Identification
Molecular formula
C23H34O5
CAS number
1672-46-4
IUPAC name
3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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, digoxigenin is typically in a solid state, appearing as white crystals or crystalline powder.

Melting point (Celsius)
255.00
Melting point (Kelvin)
528.15
Boiling point (Celsius)
639.00
Boiling point (Kelvin)
912.15
General information
Molecular weight
390.51g/mol
Molar mass
390.5050g/mol
Density
1.2600g/cm3
Appearence

Digoxigenin is typically a colorless crystalline compound. However, it can also appear as a white powder depending on its form and purity. It is often used as a biochemical marker due to its distinctive structure and properties.

Comment on solubility

Solubility of 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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 quite complex due to its intricate molecular structure and presence of multiple hydroxyl groups.

  • Hydroxyl Groups: The presence of three hydroxyl groups (–OH) typically enhances solubility in polar solvents, making the compound more amenable to dissolve in aqueous solutions.
  • Cyclic Structure: The fused cyclic structure may impart rigidity, which can restrict the molecular motion necessary for solubility, particularly in non-polar solvents.
  • Solvent Polarity: It is likely to be more soluble in polar solvents (e.g., water, methanol), while exhibiting limited solubility in non-polar solvents (e.g., hexane, benzene).
  • Interactions: The intermolecular interactions such as hydrogen bonding due to hydroxyl groups can also play a significant role in solubility characteristics.

Overall, it can be stated that the solubility of this compound is influenced by its unique stereochemistry and functional groups, indicating a potential for reasonable solubility in polar environments while maintaining limited solubility in non-polar conditions.

Interesting facts

Interesting Facts about 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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 belongs to a class of molecules known for their multifaceted roles in biological systems, particularly in the realm of medicinal chemistry. Here are some intriguing points about this particular compound:

  • Biological Activity: Compounds with similar structures have been researched for their pharmacological properties, including potential anti-inflammatory and anticancer activities.
  • Structural Complexity: The intricate stereochemistry of this compound highlights the importance of chirality in drug design. The specified stereocenters can significantly influence the biological activity of the molecule.
  • Natural Sources: Many compounds bearing a furan moiety are derived from natural products. This particular structure may be inspired by natural steroids or terpenoids, which often influence hormone regulation.
  • Research Potential: As scientists explore structural modifications, such compounds may serve as invaluable templates for the development of new therapeutic agents.
  • Environmental Influence: Compounds like this one can interact with biological systems in both beneficial and harmful ways — understanding these interactions is key in fields such as toxicology and environmental chemistry.

In conclusion, the sophisticated nature of this compound opens doors to numerous avenues of research in pharmacology and molecular biology. As we continue to unravel the complexities of such molecules, we enhance our understanding of their potential applications and implications in various areas of science.

Synonyms
Digoxigenin
Lanadigenin
Digoxigenine
HSDB 7108
NQ1SX9LNAU
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3beta,5beta,12beta)-
CHEBI:42098
EINECS 216-806-2
BRN 0096479
DTXSID6051778
DIGOXIGENIN [MI]
DIGOXIGENIN [HSDB]
3-beta,12-beta,14-Trihydroxy-card-20(22)-enolide
3-beta,12,14-Trioxy-digen-(20:22)-olid [German]
3-beta,12,14-Trioxy-carden-(20:22)-olid [German]
Cardogenen-(20:22)-triol-(3-beta,12,14) [German]
3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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
DTXCID9030333
3-beta,12,14-Trioxy-carden-(20:22)-olid
3-beta,12,14-Trioxy-digen-(20:22)-olid
(3beta,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide
5-18-04-00380 (Beilstein Handbook Reference)
delta-sup(20:22)-3-beta,12-beta,14,21-Tetrahydroxynorcholenic acid lactone
CARDOGENEN-(20:22)-TRIOL-(3-beta,12,14)
3beta,12beta,14-trihydroxy-5beta-card-20(22)-enolide
DIGOXIN IMPURITY C [EP IMPURITY]
5-beta-CARD-20(22)-ENOLIDE, 3-beta,12-beta,14-TRIHYDROXY-
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3-beta,5-beta,12-beta)-
3.BETA.,12.BETA.,14-TRIHYDROXY-5.BETA.-CARD-20(22)-ENOLIDE
DIGOXIN IMPURITY C (EP IMPURITY)
12.beta.-Hydroxydigitoxigenin
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3.beta.,5.beta.,12.beta.)-
3-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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
3-.beta.,12,14-Trioxy-carden-(20:22)-olid
3-.beta.,12,14-Trioxy-digen-(20:22)-olid
Cardogenen-(20:22)-triol-(3.beta.,12,14)
12beta-Hydroxydigitoxigenin
3-.beta.,12-.beta.,14-Trihydroxy-card-20(22)-enolide
3,12,14-Trihydroxycard-20(22)-enolide-, (3.beta.,12.beta.)-
5-.beta.-Card-20(22)-enolide, 3-.beta.,12-.beta.,14-trihydroxy-
.delta.(20:22)-3-.beta.,12-.beta.,14,21-Tetrahydroxynorcholenic acid lactone
Cardogenen-(20:22)-triol-(3beta,12,14)
3-beta,12,14-Trihydroxy-card-20(22)enolide
5-beta-Card-20(22)-enolide,3,12,14-trihydroxy-,
3,12,14-Trihydroxycard-20(22)-enolide-, (3beta,12beta)-
Card-20(22)-enolide,3,12,14trihydroxy-,(3-beta,5-beta,12-beta)-
delta(20:22)-3-beta,12-beta,14,21-Tetrahydroxynorcholenic acid lactone
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3-beta,5-beta,12-beta)-(9CI)
shibstmrcdjxln-syioraatsa-n
shibstmrcdjxln-uhfffaoysa-n
1672-46-4
3beta,12beta,14-Trihydroxy-5beta,20(22)-cardenolide
4-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3ss,5ss,12ss)-
3beta,12beta,14beta,21-Tetrahydroxy-20(22)-norcholenic acid lactone
SR-01000841253
UNII-NQ1SX9LNAU
Lanadigigenin
1lke
CAS-1672-46-4
4j8t
4j9a
Prestwick0_000883
Prestwick1_000883
Prestwick2_000883
Prestwick3_000883
bmse000735
Epitope ID:180303
CHEMBL1153
SCHEMBL21105
BSPBio_000666
MLS002154050
SPBio_002885
BPBio1_000734
Digoxigenin, analytical standard
SHIBSTMRCDJXLN-KCZCNTNESA-N
BDBM225707
CS337
HMS1570B08
HMS2097B08
HMS2233P09
HMS3714B08
HY-B1025
Tox21_303893
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3|A,5|A,12|A)-
LMST01120008
AKOS015915909
CCG-220883
CS-4542
DB03671
FD44522
NCGC00017309-03
NCGC00142481-02
NCGC00357149-01
AS-79043
SMR001233370
AB00513944
NS00025482
F85214
AB00513944_05
Q420728
5beta,20(22)-Cardenolide-3beta,12beta,14-triol
SR-01000841253-2
SR-01000841253-3
BRD-K18619710-001-03-7
BRD-K18619710-001-14-4
Digoxigenin, European Pharmacopoeia (EP) Reference Standard
(3alpha,5beta,8alpha,12beta)-3,12,14-trihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3,12,14-trihydroxy-, (3.beta.,5.beta,12.beta.)-
3b,12b,14b,21-Tetrahydroxy-20(22)-norcholenic acid lactone;3b,12b,14-Trihydroxy-5b,20(22)-cardenolide;Lanadigigenin;5b,20(22)-Carden olide-3b,12b,14-triol