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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
9-acetyl-7-[4-[[4-[[[6-[(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl)oxy]-3-hydroxy-2-methyl-tetrahydropyran-4-yl]amino]methyl]phenyl]methylamino]-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
State
State

At room temperature, doxorubicin is typically present as a solid, specifically in the form of its hydrochloride salt, which appears as a red to orange-red lyophilized powder. It is stable under normal laboratory conditions.

Melting point (Celsius)
207.00
Melting point (Kelvin)
480.00
Boiling point (Celsius)
354.00
Boiling point (Kelvin)
627.00
General information
Molecular weight
543.53g/mol
Molar mass
543.5290g/mol
Density
1.5930g/cm3
Appearence

Doxorubicin hydrochloride appears as a red to orange-red lyophilized powder. It is highly soluble in water, providing a bright red solution. The intense red color is characteristic of anthracycline compounds.

Comment on solubility

Solubility of 9-acetyl-7-[4-[[4-[[[6-[(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl)oxy]-3-hydroxy-2-methyl-tetrahydropyran-4-yl]amino]methyl]phenyl]methylamino]-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione (C27H29N1O11)

The solubility of 9-acetyl-7-[4-[[4-[[[6-[(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl)oxy]-3-hydroxy-2-methyl-tetrahydropyran-4-yl]amino]methyl]phenyl]methylamino]-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione is determined by various factors related to its complex structure. Here are some key points to consider:

  • Polar Groups: The presence of multiple hydroxyl (–OH) and methoxy (–OCH3) groups suggests that the compound may exhibit a degree of polar character, which could enhance its solubility in polar solvents such as water and alcohols.
  • Hydrophobic Regions: Conversely, the large hydrocarbon (aromatic and tetracene) portions of the structure may lead to limited solubility in highly polar solvents, resulting in better solubility in non-polar organic solvents.
  • Specific Interactions: Hydrogen bonding due to hydroxyl groups can further influence solubility. These groups may engage in hydrogen bonding with solvent molecules, potentially increasing solubility in compatible solvents.
  • Solvent Compatibility: It is likely that solubility varies significantly based on the solvent used; thus, experimentation with a range of solvents is advisable to determine optimal conditions.

In summary, the intricate balance between polar and non-polar characteristics in 9-acetyl-7-[...]-5,12-dione suggests that solubility will vary greatly depending on the chosen solvent. Testing in various environments could yield fascinating insights.

Interesting facts

Interesting Facts about 9-acetyl-7-[4-[[4-[[[6-[(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl)oxy]-3-hydroxy-2-methyl-tetrahydropyran-4-yl]amino]methyl]phenyl]methylamino]-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

This compound, with its extensive molecular structure comprised of multiple functional groups, showcases the fascinating world of synthetic organic chemistry. One of the standout features of this compound is its ability to exhibit a variety of biological activities, making it a potential candidate for therapeutic applications.

Key Highlights:

  • Complex Structure: The intricate arrangement of hydroxyl, acetyl, and methoxy groups contributes to its unique chemical properties.
  • Potential Biological Activity: Many derivatives of tetracene structures have been reported to display anti-cancer, anti-inflammatory, and antimicrobial effects.
  • Multifunctionality: The presence of multiple functional groups suggests that this compound can interact with various biological targets.
  • Synthetic Challenges: The synthesis of such complex compounds often involves multiple steps and the careful selection of reagents and conditions, making it a true testament to the innovations in organic synthesis today.

As we delve deeper into the study of such compounds, it's essential to consider their structure-activity relationships to understand how modifications can enhance their efficacy.

In summary, 9-acetyl-7-[4-[[4-[[[6-[(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl)oxy]-3-hydroxy-2-methyl-tetrahydropyran-4-yl]amino]methyl]phenyl]methylamino]-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione exemplifies the excitement and complexity inherent in modern chemistry research. The quest to harness the potential of such compounds can lead to significant advancements in medicinal chemistry and materials science.

Synonyms
NCGC00185823-01