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Doxorubicin Hydrochloride

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Identification
Molecular formula
C27H30ClNO11
CAS number
25316-40-9
IUPAC name
[(1S,4aS,11R,11aR,12S,12aR)-3-[amino(hydroxy)methylene]-4a,6,7,12-tetrahydroxy-11-methyl-2,4,5-trioxo-11,11a,12,12a-tetrahydro-1H-tetracen-1-yl]-dimethyl-ammonium;chloride
State
State

At room temperature, Doxorubicin Hydrochloride is a solid. It is typically stored as a powder and reconstituted into a solution for intravenous administration.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
252.00
Boiling point (Kelvin)
525.15
General information
Molecular weight
579.99g/mol
Molar mass
579.9850g/mol
Density
1.5780g/cm3
Appearence

Doxorubicin Hydrochloride appears as a red-orange, crystalline powder. It is a notable chemotherapeutic agent used primarily in cancer treatment. The intense color is typical for anthracycline class drugs.

Comment on solubility

Solubility of [(1S,4aS,11R,11aR,12S,12aR)-3-[amino(hydroxy)methylene]-4a,6,7,12-tetrahydroxy-11-methyl-2,4,5-trioxo-11,11a,12,12a-tetrahydro-1H-tetracen-1-yl]-dimethyl-ammonium;chloride

The solubility of complex compounds like the one mentioned can vary significantly based on several factors. Generally, compounds containing quaternary ammonium ions, such as the dimethyl-ammonium group in this case, tend to exhibit higher solubility in water due to their ionic nature. Such compounds can also interact favorably with polar solvents.

Key elements influencing solubility include:

  • Polarity: The ionic structure increases polarity, promoting solvation in polar solvents.
  • Hydrogen Bonding: Presence of hydroxyl (-OH) groups allows for hydrogen bonding, enhancing solubility in water.
  • Temperature: Increased temperature often increases solubility for many compounds, allowing for better interaction with solvent molecules.

However, it is essential to note:

  • Despite the favorable characteristics, solubility can still be pH-dependent, particularly for amino groups. Changes in pH may protonate or deprotonate these groups, thereby affecting solubility.
  • The larger and more complex structure can introduce steric hindrance, potentially impacting the rate at which the compound dissolves.

In conclusion, while the compound is likely to exhibit decent water solubility due to its ionic nature and hydroxyl groups, actual solubility levels should be analyzed under specific conditions to obtain a precise understanding.

Interesting facts

Interesting Facts about the Compound

The compound known as (1S,4aS,11R,11aR,12S,12aR)-3-[amino(hydroxy)methylene]-4a,6,7,12-tetrahydroxy-11-methyl-2,4,5-trioxo-11,11a,12,12a-tetrahydro-1H-tetracen-1-yl]-dimethyl-ammonium;chloride presents a fascinating blend of structure and function that captures the attention of chemists and biologists alike. Here are some noteworthy points:

  • Diverse Functional Groups: The compound features multiple functional groups, including amino, hydroxyl, and methylene, which contribute to its reactivity and biological activity.
  • Use in Medicinal Chemistry: Compounds with similar structures are often explored for their potential therapeutic applications, especially in developing antibiotics or anti-cancer agents.
  • Stability and Interactions: The presence of quaternary ammonium groups enhances stability and solubility, which is essential for biological activity and drug formulation.
  • Fascinating Stereochemistry: The stereochemical configuration indicated by the (S) and (R) notations indicates the compound's complex three-dimensional structure, which is crucial for its interaction with biological targets.
  • Natural Inspiration: Many complex organic compounds, like this one, often draw inspiration from naturally occurring substances, signifying a profound relationship between natural products and synthetic chemistry.

This compound exemplifies the intersection of structure and function in chemistry, revealing how intricate molecular arrangements can lead to significant biological implications. As researchers continue to investigate and analyze such compounds, the opportunities for innovation and discovery remain vast.