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Doxorubicin

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

Doxorubicin is typically in solid state at room temperature given its melting point. As a crystalline powder, it is stable and requires reconstitution in a solvent for use in clinical applications.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
340.00
Boiling point (Kelvin)
613.15
General information
Molecular weight
543.52g/mol
Molar mass
543.5190g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin typically appears as a red-orange crystalline powder. It is often supplied in a lyophilized form for clinical settings, where it is used as an injectable solution in chemotherapy treatments.

Comment on solubility

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

The solubility of the compound with the formula C27H29N1O11 reflects its complex molecular structure and the presence of various functional groups. Generally, solubility can be influenced by several factors:

  • Polar vs. Non-polar Interactions: The presence of hydroxyl (–OH) and amino (–NH2) groups suggests that this compound may have some degree of polar character, potentially enhancing its solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds through the hydroxyl and amino groups typically increases solubility in aqueous environments.
  • Chain Length and Molecular Weight: Despite the polar functional groups, the overall large molecular size and weight might hinder its complete solubility, particularly in organic solvents.
  • Solvent Polarity: Solubility will vary significantly in different solvents; for instance, it might be more soluble in alcohols than in non-polar hydrocarbons.

To encapsulate the solubility characteristics:

  • Expected higher solubility in polar solvents
  • Potential challenges in complete dissolution due to its bulkiness
  • Hydrogen bonding competence may lead to enhanced solubility in a range of conditions

Understanding these solubility dynamics is crucial, as they can affect the compound's behavior in various applications and formulations.

Interesting facts

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

This fascinating compound, known for its complex structure and unique properties, presents a rich tapestry of chemical characteristics. Here are some engaging facts:

  • Multifunctional Groups: The presence of multiple functional groups, such as amino, hydroxy, and dimethylamino, highlights its potential for engaging in various chemical reactions. This diversity enhances its utility in the field of medicinal chemistry.
  • Natural Occurrence: Compounds with similar structural motifs are often derived from natural sources. They are frequently explored for their biological activity, making them candidates for drug discovery.
  • Intriguing Structure: The tetrahydrotetracene core contributes to the compound's unique physicochemical properties and biological activity. Tetracenes are interesting molecules, especially in the context of organic semiconductors.
  • Research Potential: Owing to its notable structure, this compound may play a crucial role in the synthesis of novel pharmaceuticals. Its structural complexity makes it a favorable subject of study for exploring structure-activity relationships in drug design.
  • Analytical Techniques: Analyzing such a complex molecule requires advanced analytical techniques, including NMR spectroscopy and mass spectrometry. These methods help chemists unravel the intricate details of its structure and confirm its identity.
  • Educational Significance: For chemistry students, working with compounds like this provides excellent learning opportunities in organic synthesis and the interplay between structure and reactivity. It showcases the beauty of organic chemistry in designing intricate molecules.

In conclusion, (4S,4aS,6S,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione serves as a perfect example of the intricate relationships between molecular structure and biological activity, paving the way for further exploration and discovery in the field of chemistry.