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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
(6S)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State

At room temperature, doxorubicin is generally found as a crystalline solid. Its hydrochloride salt form is used in medicines due to its solubility and stability at room conditions.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.10
Boiling point (Celsius)
693.10
Boiling point (Kelvin)
966.30
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.5600g/cm3
Appearence

Doxorubicin appears as a dark red or red-orange powder. It is highly soluble in water, forming a red solution. The compound is typically available in its hydrochloride salt form for pharmaceutical uses.

Comment on solubility

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

The solubility of the compound (6S)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione can be influenced by multiple factors due to its complex structure. Here are some key points to consider:

  • Polarity: Given the presence of multiple hydroxyl groups, one might expect the compound to exhibit relatively high polarity, which could enhance its solubility in polar solvents such as water.
  • Hydrogen Bonding: The amino and hydroxy functional groups are capable of forming hydrogen bonds, which generally improves solubility in polar solvents while potentially reducing solubility in non-polar solvents.
  • Saturation: The degree of saturation in the compound's structure may also affect solubility; more saturated compounds often have lower solubility in non-polar solvents.
  • Temperature: Solubility can vary with temperature; typically, increasing the temperature enhances the solubility of solids in liquids.
  • pH Dependence: The solubility of compounds containing amine groups can significantly alter with pH, potentially affecting solubility in aqueous environments.

In conclusion, predicting the solubility of such a complex molecular structure is challenging without empirical data. The interplay of functional groups suggests that it may be soluble in polar solvents, but detailed solubility studies would be necessary to quantify this property accurately.

Interesting facts

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

The compound known as (6S)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione is a fascinating example of a complex organic molecule that showcases the intricate relationships between structure and function in chemistry. Here are some engaging aspects to consider:

  • Multiple Hydroxy Groups: This compound features five hydroxy groups, which typically contribute to its solubility in polar solvents and influence its reactivity. These functional groups can engage in hydrogen bonding, affecting various properties such as boiling point and stability.
  • Dimethylamino Structure: The presence of a dimethylamino group can enhance the compound's basicity. This functional group plays a critical role in defining the compound's behavior in biological systems, possibly affecting its interaction with biological targets or receptors.
  • Potential Biological Activity: Given the complexity and diverse functional groups, this compound could have significant implications in medicinal chemistry. Compounds with similar structures have been researched for their potential therapeutic effects, including antimicrobial and anticancer activities.
  • Stereochemistry: The designation of (6S) indicates specific stereochemistry, which is crucial in the realm of pharmaceuticals. The spatial arrangement of atoms affects how the compound interacts with biological systems, potentially leading to vastly different outcomes in efficacy and safety.
  • Color and Light Absorption: Compounds that belong to the tetracene family, known for their conjugated systems, can exhibit interesting optical properties. This compound may absorb light and participate in photochemical reactions, offering a wide field for research in materials science and photonics.

In summary, (6S)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione embodies a rich tapestry of chemical features that not only enhances its potential utility in scientific research but also adds a layer of complexity that makes it a compelling subject for further study.