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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
(4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione
State
State

Doxorubicin is a solid at room temperature, commonly supplied in its hydrochloride salt form for stability. It is primarily used in the medical field as an anticancer drug.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
543.53g/mol
Molar mass
543.5260g/mol
Density
1.2609g/cm3
Appearence

Doxorubicin is an orange-red solid, typically found as crystalline powder or small crystals. It is often handled as a hydrochloride salt which is similarly colored.

Comment on solubility

Solubility of (4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione

The solubility of the compound C27H29N1O11 can be described considering the following factors:

  • Polarity: Due to the presence of multiple hydroxyl (-OH) groups and amino (-NH2) functionalities, this compound is expected to exhibit high polarity, suggesting a potential for increased solubility in polar solvents such as water.
  • Hydrogen Bonding: The ability to form hydrogen bonds through its hydroxyl and amino groups further enhances its solubility in polar solvents. As a rule of thumb, compounds that can form hydrogen bonds often have favorable solubility in aqueous solutions.
  • Solvent Type: In contrast, the presence of large hydrophobic regions, such as the dimethylamino groups, could impede solubility in non-polar solvents. Hence, this compound is likely to have limited solubility in organic solvents like hexane or toluene.

In summary, while the compound is expected to be soluble in polar solvents due to its polar functional groups, its solubility in non-polar solvents is likely to be low. As a general rule, the phrase “like dissolves like” applies, meaning that compounds with similar polarities will more readily dissolve in one another.

Interesting facts

Interesting Facts about (4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione

This fascinating compound, with its complex structure, belongs to the class of organic compounds with significant biological activity and unique properties. Its intricate molecular arrangement not only contributes to its potential applications but also highlights the beauty of organic chemistry. Here are some interesting aspects regarding this compound:

  • Structural Complexity: The stereochemistry of this compound is particularly notable, featuring multiple chiral centers which can lead to varied biological interactions.
  • Biological Significance: Compounds with such structures are often investigated for their therapeutic potential. Some derivatives are known for their anticancer properties.
  • Dimethylamino Groups: The presence of dimethylamino groups may enhance the compound's solubility and reactivity, impacting its pharmacological behavior.
  • Hydroxy Functionality: Hydroxy groups generally play a crucial role in the formation of hydrogen bonds, which can influence the compound's interactions with biological macromolecules.
  • Environmental Aspect: Investigating compounds like this may lead to the development of environmentally friendly alternatives in pharmaceuticals and agrochemicals.

The exploration of such compounds is fundamental in the field of medicinal chemistry, where understanding structure-activity relationships can lead to breakthroughs in drug design. As scientists continue to unravel the mysteries of complex organic compounds, the potential for new therapeutic agents grows, driven by the intricate relationship between molecular structure and biological function.

In the words of renowned chemist and Nobel laureate, “The great discoveries are the conceptions of that spirit of curiosity which is the origin of science.” This compound exemplifies that spirit, showcasing the wonders of chemical research and discovery.