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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
2-[[[[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxy-methyl]amino]methylamino]-6-amino-hexanoic acid
State
State

At room temperature, doxorubicin is a solid compound. It is generally provided as a hydrochloride salt in clinical settings, enhancing its solubility for intravenous administration in liquid or solution form.

Melting point (Celsius)
208.00
Melting point (Kelvin)
481.15
Boiling point (Celsius)
980.30
Boiling point (Kelvin)
1 253.30
General information
Molecular weight
579.99g/mol
Molar mass
579.9880g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin typically appears as a red-orange, crystalline powder. It is often seen in its hydrochloride form for clinical use, which enhances its solubility in water, resulting in a more orange-red solution.

Comment on solubility

Solubility of 2-[[[[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxy-methyl]amino]methylamino]-6-amino-hexanoic acid

The solubility of complex organic compounds like 2-[[[[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxy-methyl]amino]methylamino]-6-amino-hexanoic acid can vary significantly based on several factors. Here are a few key points to consider:

  • Polarity: The presence of multiple hydroxy groups and amino groups suggests that this compound is likely to be polar. Polar compounds tend to be soluble in polar solvents, such as water.
  • Hydrogen Bonding: The abundance of hydroxyl (-OH) and amino (-NH2) groups enables strong hydrogen bonding with solvent molecules, enhancing solubility in aqueous solutions.
  • Structural Complexity: The intricate structure of this compound may create steric hindrance, potentially affecting solubility in non-polar solvents.
  • pH Sensitivity: As an amino acid, the solubility could also be influenced by the pH of the solution, which may impact the ionization state of the amino and carboxyl groups.

The solubility should also be experimentally determined, as theoretical predictions cannot always capture the nuances of real-world behavior. In conclusion, while the potential for high solubility in polar solvents exists due to the multifunctional grouping within its structure, empirical data is necessary for definitive characterization.

Interesting facts

Interesting Facts About 2-[[[[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxy-methyl]amino]methylamino]-6-amino-hexanoic acid

This intriguing compound is a derivative of amino acids, featuring a complex structure that illustrates the diversity of organic chemistry. It exemplifies how modifications in the molecular framework can lead to significant changes in biological activity. Below are some remarkable aspects of this compound:

  • Complex Structure: The compound consists of multiple functional groups, including amino and hydroxyl groups. This complexity can be responsible for its potential to interact with various biological targets.
  • Potential Biological Applications: Given its unique molecular architecture, it might exhibit interesting pharmacological properties, making it a candidate for further research in drug development.
  • Stereochemistry: The specific stereochemistry indicated by the notations (4aS, 6S, 12aS) suggests that the orientation of its atoms is critical, likely influencing how it interacts with biological systems. As the renowned chemist Linus Pauling once said, "The structure of a substance can greatly affect its reactivity."
  • Amino Acid Properties: Being an amino acid derivative, it shares properties with common amino acids, allowing it to participate in peptide formation, which is essential for protein synthesis.
  • Research Interest: Researchers are continually exploring the impact of structural variations in amino acid derivatives on their activity and efficacy, making this compound an interesting subject for study.
  • Potential Use in Synthesis: The functional groups present in this compound may serve as key building blocks in the synthesis of more complex molecules.

In conclusion, 2-[[[[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxy-methyl]amino]methylamino]-6-amino-hexanoic acid not only displays a fascinating chemical structure but also enhances our understanding of how modifications at the molecular level can lead to diverse biological implications.