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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
3-[3-[5-[5-(4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-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, digitoxin is typically in a solid state. It can be processed into various pharmaceutical formulations for medical use.

Melting point (Celsius)
243.00
Melting point (Kelvin)
516.15
Boiling point (Celsius)
762.20
Boiling point (Kelvin)
1 035.35
General information
Molecular weight
764.96g/mol
Molar mass
764.9640g/mol
Density
1.3300g/cm3
Appearence

Digitoxin is typically a white, crystalline powder. It is a cardiac glycoside and is known for its bitter taste. The compound may appear differently based on its impurities or formulation.

Comment on solubility

Solubility of 3-[3-[5-[5-(4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-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 (C41H64O13)

The solubility of the compound 3-[3-[5-[5-(4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-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 highly intricate structure. Here are some key points to consider:

  • Polarity: The presence of several hydroxyl groups (-OH) suggests that this compound may exhibit polar characteristics, potentially enhancing its solubility in polar solvents like water.
  • Hydroxyl Groups: Hydroxyl functional groups can form hydrogen bonds with water, which can lead to increased solubility.
  • Hydrophobic Regions: Despite the polar nature imparted by hydroxyl groups, the larger hydrophobic hydrocarbon segments might limit solubility in water.
  • Practical Solubility: Solubility testing in a variety of solvents, such as alcohols or DMF, might yield different results based on solvent polarity.
  • General Observation: It's common for large organic compounds with both hydrophilic and hydrophobic regions to display variable solubility profiles, depending on the solvent system used.

In summary, while the polar nature of the multiple hydroxyl groups suggests favorable interactions with polar solvents, the extensive and complex hydrophobic parts of the molecule may hinder complete solubility, leading to a nuanced and solvent-dependent solubility profile.

Interesting facts

Interesting Facts about 3-[3-[5-[5-(4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-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 represents a fascinating example of complex organic chemistry and illustrates the intricate relationships found within natural products. Its structure features multiple functional groups and stereocenters, showcasing not only the diversity of organic compounds but also the potential for intricate biosynthesis in living organisms.

Key Highlights of the Compound:

  • Natural Source: Compounds of this complexity often derive from plant secondary metabolites, which play critical roles in plant defense mechanisms and interactions with other organisms.
  • Biological Activity: Some compounds with furan-5-one and tetrahydropyran structures have been studied for their potential medicinal properties, such as anti-inflammatory and antioxidant effects.
  • Synthesis Challenge: The synthesis of such large, multi-ring compounds is a significant challenge in organic chemistry, requiring advanced techniques in both synthetic and analytical chemistry.
  • Research Interest: Scientists are continually exploring these types of compounds for their applications in pharmaceuticals, which can include developing new drugs and understanding biological pathways.

As the chemist Robert H. Grubbs once said, “Chemistry is the essence of life.” This compound exemplifies how complex structures contribute to life’s diversity, reflecting the beauty and intricacy of the molecular world. The study of such compounds not only illuminates their function and mechanism but also inspires future innovations in both chemistry and biology.

Synonyms
Lanicor
Cogoxin
Digitalis glycoside
3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-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
Lanacordin
Lenoxin
NSC95100
Lanoxine-PG
3-(3-(5-(5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-12,14-dihydroxy-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-{[2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
12.beta.-Hydroxydigitoxin
CHEMBL20692
SCHEMBL126382
DTXSID10860258
LTMHDMANZUZIPE-UHFFFAOYSA-N
BBL033712
STL372822
AKOS025247958
NCGC00248443-01
VS-12230
DB-045400
D6003
AP-163/40806811
1380169-08-3
3-((2,6-Dideoxy-4-O-[2,6-dideoxy-4-O-(2,6-dideoxyhexopyranosyl)hexopyranosyl]hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide, (3.beta.,5.beta.,12.beta.)- #
3-[(O-2,6-Dideoxyhexopyranosyl-(1a4)-O-2,6-dideoxyhexopyranosyl-(1a4)-2,6-dideoxyhexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide
3.beta.-[(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.beta.,14-dihydroxy-5.beta.-card-20(22)-enolide
4-(3-((5-((5-((4,5-dihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-12,14-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)furan-2(5h)-one
4-(7-{[5-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl)-2,5-dihydrofuran-2-one
Card-20(22)-enolide, 3-((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.)-
Card-20(22)-enolide, 3-[(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.)-
Card-20(22)-enolide, 3-[(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.)-