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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State
Doxorubicin is typically found as a solid at room temperature. It is stable under standard conditions and is supplied as a hydrochloride salt for medical use.
Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
430.50
Boiling point (Kelvin)
703.70
General information
Molecular weight
543.52g/mol
Molar mass
543.5250g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin appears as a red-orange crystalline solid. It is known for its characteristic vibrant color, which is often used in its identification. When dissolved in water, it forms a clear red solution.

Comment on solubility

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

The solubility of a complex organic compound like (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione can be influenced by various factors due to its intricate structure and the presence of multiple functional groups.

  • Polarity: Compounds with polar functional groups, such as hydroxyl (-OH) or amino (-NH2), typically exhibit greater solubility in polar solvents, particularly water. The presence of these groups suggests some solubility in aqueous solutions.
  • Hydrophobic Regions: The compound also contains hydrophobic regions due to its tetracene backbone, which may limit solubility in polar environments, promoting solubility in organic solvents like ethanol or DMSO.
  • Hydrogen Bonding: The potential for hydrogen bonding increases likely solubility in solvents capable of hydrogen bond interactions, enhancing dissolution.

Overall, solubility can vary significantly based on the solvent used. It is crucial to perform solubility tests in various solvents to comprehensively determine the solubility profile of this compound. Adequate knowledge of the solubilizing medium is essential for practical applications in chemical research and pharmaceutical formulations.

Interesting facts

Interesting Facts About (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

This compound, a fascinating member of the tetracene family, presents a rich tapestry of structural complexity and biological potential. Given its intricate arrangement of functional groups, it exhibits unique properties that make it a subject of interest in both organic chemistry and medicinal applications.

  • Structural Diversity: The presence of diverse functional groups—such as hydroxy and dimethylamino—contributes significantly to the compound's reactivity and interaction with biological systems.
  • Potential Biological Activity: Compounds like this one are often explored for their pharmacological properties. The amine and hydroxy groups may enhance interactions with biological targets, which is exciting for drug design.
  • Multi-stage Synthesis: The synthesis of such a complex molecule typically requires multi-step reactions, highlighting the ingenuity of modern synthetic chemistry. Researchers often utilize a combination of techniques such as Friedel-Crafts reactions and cyclization processes.
  • Applications in Material Science: Tetracenes are known for their electronic properties, making compounds like this one candidates for organic semiconductors and other advanced materials.

In the realm of chemistry, this compound serves as a reminder of the intersection between structure and function. According to a prominent chemist, “The beauty of organic compounds lies in their diversity and the stories they tell through their structures.” Studying compounds like this one deepens our understanding of chemical behaviors and leads to practical applications across various fields.

The exploration of this compound continues to inspire researchers to delve into its properties, potential applications, and synthesis, pushing the boundaries of what is currently understood in the world of organic molecules.