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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
(4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State

At room temperature, doxorubicin is a solid, typically handled as a hydrochloride salt which is a red-orange powder.

Melting point (Celsius)
217.00
Melting point (Kelvin)
490.15
Boiling point (Celsius)
860.15
Boiling point (Kelvin)
1 133.30
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin is a red-orange crystalline powder.

Comment on solubility

Solubility of (4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

The solubility of the compound (4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione can be influenced by several factors:

  • Polarity: Given its numerous hydroxy groups, the compound is likely to possess high polarity, which generally enhances solubility in polar solvents like water.
  • Hydrogen Bonding: The presence of multiple hydroxyl (-OH) groups suggests a capacity for strong hydrogen bonding with solvents, further promoting solubility.
  • Amine Functionality: The dimethylamino group may introduce additional solubility characteristics, particularly in organic solvents.
  • Structural Complexity: The intricate polycyclic framework may limit solubility due to steric hindrance, potentially decreasing solubility in non-polar solvents.

In summary, while the compound is likely to be soluble in polar solvents due to its functional groups, solubility in non-polar media may be limited. Understanding the solubility is crucial for its application in various fields.

Interesting facts

Exploring the Compound: (4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

This complex organic compound presents a fascinating intersection of organic chemistry and potential medicinal applications. Its structural uniqueness and intricate stereochemistry make it a notable subject for research. Here are some intriguing aspects:

  • Stereochemistry: The compound possesses multiple stereocenters, indicated by its chirality. Understanding its chirality is crucial for predicting its reactivity and interactions with biological systems.
  • Functional Groups: With functional groups such as amino, hydroxy, and dimethylamino, this compound has the potential to form various interactions with other molecules, showcasing its possible roles in biochemical pathways.
  • Potential Applications: The presence of several hydroxy groups combined with the amino group suggests that this compound may have applications in pharmaceuticals, particularly in the design of biologically active compounds.
  • Structure-Activity Relationship (SAR): The intricate structure allows chemists to study the SAR, offering insights into how the changes in certain functional groups or configurations affect the biological activity and properties of the compound.
  • Natural Analogues: Structures similar to this compound can often be found in nature, indicating a possible evolutionary significance or utilization in certain biological processes.

As researchers delve deeper into its properties and interactions, this compound could unveil new pathways for drug design and synthesis, demonstrating the ever-evolving landscape of chemistry and biochemistry.