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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
(4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
State
State

At room temperature, doxorubicin is generally a solid in its pure form. It is commonly used in a lyophilized form for pharmaceutical preparations, where it is reconstituted into a liquid for intravenous administration as a chemotherapy drug.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
289.00
Boiling point (Kelvin)
562.15
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.5608g/cm3
Appearence

Doxorubicin typically appears as a red to red-orange crystalline powder. The crystalline nature of doxorubicin is attributed to its stable structure which is used in pharmaceutical applications. Upon exposure to light, it can degrade, hence it is usually stored under dark conditions to maintain its integrity.

Comment on solubility

Solubility Characteristics

The compound (4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione presents fascinating solubility properties that are influenced by its complex structure. Understanding its solubility can be crucial for applications in various fields:

  • Polarity: The presence of multiple hydroxyl groups (–OH) contributes significantly to the molecule's polarity, enhancing its ability to dissolve in polar solvents such as water.
  • Hydrogen Bonding: The amino and hydroxy groups are capable of forming hydrogen bonds, which often increase solubility in aqueous environments, making the compound more readily available for biological interactions.
  • Chlorine Substitution: The inclusion of a chlorine atom can affect the overall solubility by introducing additional nonpolar character, which might reduce solubility in strictly polar solvents.
  • Dimethylamino Group: This group can also influence solubility patterns due to its basic nature, which might enhance solubility in specific solvents and pH conditions.

In conclusion, the solubility of this complex compound is governed by its functional groups, which can interact with various solvents through hydrogen bonding and polarity. Consequently, the solubility may vary significantly across different solvent types:

  1. High solubility in polar solvents (e.g., water)
  2. Potentially reduced solubility in nonpolar solvents

This intricate balance of polar and nonpolar features shapes the compound's behavior in solution, making it a subject of interest for further investigation in chemical and biological contexts.

Interesting facts

Interesting Facts About (4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

This complex compound is a fascinating example of organic chemistry, showcasing the intricate nature of molecular structures. Here are some engaging facts:

  • Structural Complexity: This molecule belongs to a class of compounds known as tetracenes, which are polycyclic aromatic hydrocarbons. The complexity of its structural formula illustrates the diversity of organic compounds in terms of functionality and reactivity.
  • Biological Relevance: Compounds similar to this have been studied for their potential use in pharmaceuticals, particularly in the realm of anti-cancer agents. The presence of amino and hydroxyl groups suggests it might engage in hydrogen bonding, enhancing its interactions with biological macromolecules.
  • Chirality: The designations (4S,4aS,5aS,6S,12aS) indicate that this compound has multiple chiral centers, making its stereochemistry crucial for its biological activity. Different stereoisomers can exhibit significantly different properties and reactions in biological systems.
  • Functional Groups: The compound boasts several functional groups, including a dimethylamino group and multiple hydroxyl groups, which can strongly influence its solubility and reactivity, playing a role in drug design and synthesis.
  • Research Potential: Due to its unique molecular structure, this compound can be a target for synthetic chemists aiming to explore new pathways in organic synthesis and drug discovery, fulfilling an essential role in advancing medicinal chemistry.

In summary, this compound exemplifies the beauty and complexity of organic chemistry, providing a fertile ground for research and discovery. As scientists continue to explore such intricate structures, they often uncover valuable insights applicable to medical and technological fields.