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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
4-hydroxy-17-methyl-12,14,16-trioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
State
State

This compound is typically a solid at room temperature.

Melting point (Celsius)
213.00
Melting point (Kelvin)
486.15
Boiling point (Celsius)
657.10
Boiling point (Kelvin)
930.20
General information
Molecular weight
580.00g/mol
Molar mass
579.9880g/mol
Density
1.6000g/cm3
Appearence

The compound appears as red to reddish-orange crystalline powder.

Comment on solubility

Solubility of 4-hydroxy-17-methyl-12,14,16-trioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione (C27H29NO11)

The solubility of 4-hydroxy-17-methyl-12,14,16-trioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione in various solvents is a noteworthy aspect to consider due to its complex molecular structure. This compound's solubility can greatly influence its application in chemical processes and pharmaceuticals.

Key Factors Affecting Solubility:

  • Polarity of the Compound: The hydroxyl groups present in the structure contribute to some degree of polarity, which typically enhances solubility in polar solvents.
  • Hydrogen Bonding: The presence of hydroxyl groups allows for the formation of hydrogen bonds, potentially increasing solubility in water and some organic solvents.
  • Molecular Size: Being a larger and more complex molecule, solubility might be limited in highly non-polar solvents.

Generally, it is expected that this compound would exhibit:

  • Increased solubility in: polar solvents like water, methanol, or ethanol due to hydrogen bonding.
  • Decreased solubility in: non-polar solvents such as hexane or cyclohexane because of the mismatch in polarity.

In summary: While detailed studies on the solubility of this specific compound may be limited, its structural features suggest that it is more likely to be soluble in polar environments, providing important considerations for its practical uses in various chemical applications.

Interesting facts

Interesting Facts about 4-Hydroxy-17-methyl-12,14,16-trioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

This compound is a fascinating adduct known for its complex structure and unique properties, which makes it a subject of interest in the field of organic chemistry. Here are some engaging points about this remarkable compound:

  • Structural Complexity: With a tetracyclic framework, the structure of this compound showcases intricate stereochemistry that can lead to a multitude of isomers, each potentially having different biological activities.
  • Natural Occurrence: Compounds similar to this one are often found in various natural products, especially in certain classes of plant metabolites. They may play a role in defense mechanisms against herbivores or pathogens.
  • Potential Biological Activity: Due to its unique moieties, this compound could exhibit interesting pharmacological properties, making it a candidate for further studies in medicinal chemistry. Its analogs have been explored for various biological activities, including anti-inflammatory and anticancer effects.
  • Functional Groups: The presence of hydroxy groups contributes to the polarity of the compound, which may enhance its interaction with biological systems and improve its solubility in different solvents.
  • Challenging Synthesis: The synthesis of such complex molecules requires advanced organic synthesis techniques, often involving multiple steps and the use of protecting groups to manage the various functional groups present in the molecule.

As Mary L. O'Connell aptly remarked, "The beauty of chemistry lies not only in its precision but also in its complexity." The exploration of compounds like this exemplifies the intersection of art and science in the realm of chemical research.

Whether for academic inquiry or practical applications, 4-hydroxy-17-methyl-12,14,16-trioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione holds the promise of uncovering new insights into both synthetic and natural product chemistry.

Synonyms
Kalamycin; NSC 137443; U 19718
CHEMBL1908343
SB49672