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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
(4S,4aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State
Doxorubicin is typically found in a solid state at room temperature, often in the form of a hydrochloride salt to enhance its solubility for medical use.
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
543.5250g/mol
Density
1.5100g/cm3
Appearence
Doxorubicin is typically a red to orange-red crystalline solid. Its vivid coloration is notable, making it distinguishable from a variety of other substances in laboratory settings.
Comment on solubility

Solubility of (4S,4aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

The solubility profile of the compound C27H29NO11 reveals some intriguing characteristics that are influenced by its complex structure.

  • Polarity: The presence of multiple hydroxyl (-OH) groups and an amino (-NH2) group significantly enhances the polarity of this compound, making it more likely to dissolve in polar solvents such as water.
  • Hydrogen Bonding: The functionality provided by hydroxyl and amino groups allows for extensive hydrogen bonding interactions, which can facilitate solubility in polar environments.
  • Chlorine Atom: The presence of a chlorine atom may impact the overall solubility, contributing to steric hindrance and altering how the compound interacts with solvent molecules.
  • Dimethylamino Group: This functional group adds to the overall basicity of the compound, which may influence its solubility behavior in various solvents.

In summary, while this compound can exhibit good solubility in water due to its polar characteristics, the precise behavior may depend on the solvent system used. It is important to consider the balance between its polar and nonpolar attributes when assessing solubility in various environments.

Interesting facts

Interesting Facts about (4S,4aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

This intriguing compound, characterized by its complex structure consisting of multiple functional groups and stereochemistry, offers a wealth of unique features that captivate both chemists and enthusiasts alike. Here are some fascinating insights about it:

  • Structural Complexity: The presence of four hydroxy groups along with amino and chloro substituents contributes significantly to the compound's intricate functionality, enabling a variety of interactions with biological macromolecules.
  • Stereochemistry: Its specific stereochemical configuration (4S, 4aS, 6S, 12aS) plays a crucial role in determining the compound's reactivity and biological activity. The spatial arrangement influences how it interacts with enzymes and receptors.
  • Biological Relevance: This compound may exhibit fascinating pharmacological properties. Compounds with similar structures are often found to possess antimicrobial, anti-inflammatory, or other therapeutic activities, making them potential candidates for drug development.
  • Chirality in Chemistry: The chirality present in this compound underscores the importance of three-dimensional structure in drug design, where enantiomers can have vastly different biological effects. In some cases, one enantiomer might be therapeutic while the other could be harmful.
  • Applications in Research: Compounds like this one are often used as probes in biochemical research, helping scientists understand metabolic pathways and enzyme mechanisms due to their ability to mimic natural substrates.
  • Future Prospects: Continuous exploration of complex molecules like this may lead to the discovery of novel compounds that could pave the way for innovative treatments in various medical fields.

In conclusion, the study of such a compound transcends basic chemical analysis; it opens doors to exploring new avenues in medicinal chemistry, structural biology, and therapeutic innovations.