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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
[2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[[(4-methylpiperazin-1-yl)amino]methylene]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,19,21,24,27-heptaen-13-yl] acetate
State
State

At room temperature, doxorubicin is typically in a solid state, specifically as a crystalline powder for medical use. It is often dissolved in a solution for intravenous administration in chemotherapy treatments.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.20
Boiling point (Celsius)
956.10
Boiling point (Kelvin)
1 229.30
General information
Molecular weight
543.52g/mol
Molar mass
543.5220g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin is typically seen as a red to orange crystalline powder. It is often provided in its hydrochloride form as a red-orange powder, which is a commonly used chemotherapeutic agent.

Comment on solubility

Solubility of the Compound

The compound 2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[[[4-methylpiperazin-1-yl]amino]methylene]-6,23-dioxo-8,30-dioxa-24-azatetracyclo23[3.3.1.14,7.05,28]triaconta-1(29),2,4,19,21,24,27-heptaen-13-yl acetate (C27H29NO11) exhibits intriguing solubility characteristics that can impact its applications in various fields.

Several factors influence the solubility of this complex organic compound:

  • Hydroxyl Groups: The presence of five hydroxyl (-OH) functional groups suggests potential for significant hydrogen bonding with water molecules, which often enhances solubility in polar solvents.
  • Hydrophobic Regions: Conversely, the heptamethyl and methoxy groups provide hydrophobic characteristics that may limit solubility in aqueous environments.
  • Amine Side Chains: The 4-methylpiperazin-1-yl group can also contribute to interactions with polar solvents, yet its overall influence may depend on the extent of steric hindrance.

In citational contexts, "The solubility of a compound is often a balance between its polar and non-polar characteristics." This compound likely demonstrates limited solubility in water due to its substantial hydrophobic portions, yet may find greater solubility in organic solvents such as ethanol or dimethyl sulfoxide (DMSO).

Ultimately, understanding the solubility of such a complex compound is crucial for its practical applications in medicinal chemistry and materials science, as solubility can significantly affect bioavailability and reactivity.

Interesting facts

Interesting Facts about the Compound

This intriguing compound, known for its complex structure, showcases an exquisite arrangement of functional groups that contribute to its unique properties and potential applications in various fields, particularly in pharmaceuticals and biochemistry.

Chemical Structure and Characteristics

The compound features a remarkable architecture that includes:

  • Multiple Hydroxy Groups: The presence of five hydroxy (OH) groups enhances its polarity and solubility in biological systems, making it potentially useful in drug formulations.
  • Methoxy Substitution: The methoxy group can modify the compounds' effects in biological interactions, influencing drug activity and metabolism.
  • Heptamethyl Framework: This intricate configuration aids in stabilizing the overall structure, affecting how the molecule interacts with its environment.

Biological Significance

The compound’s extensive functionalization may lead to several biological activities, including:

  • Antimicrobial Activity: Its unique structure may exhibit properties that inhibit the growth of various microbial strains.
  • Targeted Drug Delivery: The integration of a piperazine moiety suggests potential capabilities in interacting with specific biological targets, facilitating targeted therapeutic actions.

Research and Applications

In the realm of scientific inquiry, this compound holds the potential to inspire future research. Notably:

  • Drug Development: Continuous exploration of its biological effects may yield new medications for prevalent diseases.
  • Innovative Synthesis: Its complex synthesis challenges chemists to develop new methodologies, fostering advancements in synthetic chemistry.

As a budding chemist or researcher, delving into the properties and potential applications of such compounds can open pathways to innovative solutions in healthcare and material sciences. The intricate balance of structure and function exemplified by this compound is a reminder of the beauty and complexity inherent in chemical science.