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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
(4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State

At room temperature, doxorubicin is typically used and stored in solid crystalline form, although it is administered in a liquid solution intravenously.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.5703g/cm3
Appearence

Doxorubicin typically appears as a red to orange crystalline powder. It is often provided in solution form during medical preparation where it exhibits the same coloration. The compound is known for its characteristic red-orange color which makes it distinct.

Comment on solubility

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

The solubility of this complex compound can be characterized by several important factors that influence its behavior in various solvents. Given its intricate structure, including multiple hydroxy and amino groups, one can expect it to exhibit hydrophilic properties, allowing it to dissolve well in polar solvents such as water.

Here are some key considerations regarding its solubility:

  • Polar Functional Groups: The presence of amino and hydroxy groups typically enhances solubility in water due to their ability to form hydrogen bonds.
  • Solvent Interaction: The solubility may vary significantly depending on the choice of solvent; non-polar solvents might fail to dissolve this compound effectively.
  • Concentration Effects: As is common with many solid compounds, solubility may increase with higher temperatures, making thermal conditions important in practical applications.

As the saying goes, “A compound’s solubility is a balance of its intermolecular forces.” Understanding this balance is essential to predict how this compound will behave in solution. Overall, while its exact solubility profile may require empirical investigation, the structural attributes suggest a favorable interaction with water and other polar solvents.

Interesting facts

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

This fascinating compound is a member of a broader class known as tetracenes, which are polycyclic aromatic hydrocarbons (PAHs). Tetracenes are characterized by their unique arrangement of fused benzene rings, leading to intriguing electronic and optical properties.

Significance in Research

  • Photophysical Properties: The tetrahydrotetracene structure allows for the exploration of multiple excited states, making it a subject of interest for organic solar cells and light-emitting devices.
  • Biological Activity: Compounds with amino and hydroxy groups, like this one, are often investigated for their potential pharmaceutical applications due to their ability to interact with biological molecules.
  • Complex Synthesis: The synthesis of this compound is a testament to the advances in synthetic organic chemistry, showcasing methods for constructing complex polycyclic systems.

The presence of both dimethylamino and hydroxy functional groups introduces the possibility of interesting structure-activity relationships. These functional groups can influence solubility, polarity, and reactivity, enhancing the compound’s utility.

Applications and Future Perspectives

  • Organic Electronics: With their favorable charge transport properties, tetracenes are being evaluated for use in organic semiconductors.
  • Drug Design: As a potential lead compound, its bioactive properties may lead to further modifications and enhancements for developing new therapeutic agents.
  • Research in Nanotechnology: The unique structural characteristics may enable the use of this compound in the development of nanomaterials.

In conclusion, the complexity and potential of (4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione continue to inspire chemists and researchers, highlighting the rich interplay between structure and function in organic compounds. Its role in advancing technology and medicine demonstrates the importance of exploring such intricate molecular architectures.