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Doxorubicin

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Identification
Molecular formula
C27H30N1O11
CAS number
23214-92-8
IUPAC name
[3-hydroxy-2-methyl-6-[[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]tetrahydropyran-4-yl]ammonium
State
State

At room temperature, doxorubicin is typically found in its solid state as a crystalline powder.

Melting point (Celsius)
208.00
Melting point (Kelvin)
481.20
Boiling point (Celsius)
221.70
Boiling point (Kelvin)
494.90
General information
Molecular weight
543.53g/mol
Molar mass
543.5260g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin appears as a red to orange-red crystalline solid or powder. It is often supplied as a hydrochloride salt and appears in various forms depending on the formulations used in medical applications.

Comment on solubility

Solubility of 3-hydroxy-2-methyl-6-[[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]tetrahydropyran-4-yl]ammonium

The solubility of the compound with the formula C27H30N1O11 is an intriguing topic due to its complex structure. Its solubility profile can be influenced by several factors, including:

  • Polarity: The presence of multiple hydroxyl (–OH) functional groups suggests a tendency for hydrophilicity, which often enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups are capable of forming hydrogen bonds, which typically increases interactions with solvent molecules, thereby improving solubility.
  • Molecular Weight: Given its substantial molecular weight, one might expect lower solubility in nonpolar solvents, leading to a preference for polar solvents.

While many compounds with similar functional groups exhibit good solubility in water, the specific solubility of this compound may vary significantly based on:

  1. pH: Changes in pH can affect the ionization of ammonium groups, which in turn can influence solubility.
  2. Temperature: Solubility may increase with rising temperatures, especially for complex organic molecules.
  3. Presence of other solutes: The presence of salts or organic solvents may enhance or hinder solubility through interactions.

Overall, while this compound exhibits promising prospects for solubility due to its functional groups, empirical testing is necessary to determine its exact solubility characteristics in various solvents. As the saying goes, "The only way to know is to test!"

Interesting facts

Interesting Facts About 3-Hydroxy-2-methyl-6-[[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]tetrahydropyran-4-yl]ammonium

This compound is a fascinating example of a complex organic molecule with significant implications in both medicinal chemistry and bioorganic chemistry. Below are some key points that elucidate its remarkable characteristics:

  • Structure Complexity: The compound features a tetrahydropyran ring, characteristic of many natural products, which contributes to its biological activity. The intricate fused ring system shows how variability in structure can lead to diverse functionalities.
  • Natural Sources: This compound, or derivatives thereof, can often be found in natural products such as alkaloids, which are known for their pharmacological properties. Its synthesis in the lab allows for the exploration of similar structures in nature.
  • Potential Biological Activity: Given its structural components, the compound could exhibit properties that interact with biological systems. For example, the presence of hydroxyl groups often enhances solubility and biological reactivity.
  • Application in Drug Development: Compounds of this nature can be integral in the process of drug discovery and development, especially for targeting specific receptors or pathways in diseases.
  • Research Interest: Researchers are intrigued by the compound's potential in creating new therapeutic agents. Understanding how modifications to its structure can affect activity is a subject of ongoing study.
  • Comparative Studies: This compound can serve as a reference for comparative studies in synthetically derived analogs, helping scientists to build libraries of compounds for high-throughput screening in pharmaceutical research.

Overall, the exploration of 3-hydroxy-2-methyl-6-[[3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]tetrahydropyran-4-yl]ammonium not only underscores the importance of organic synthesis but also highlights the rich potential of such compounds in advancing medicinal practices. As Marie Curie once said, "Nothing in life is to be feared, it is only to be understood." This compound is an intersection of fearlessness and understanding in the vast realm of chemistry.

Synonyms
Doxorubicin (Adriamycin) HCl
STL484057
3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-ammonio-2,3,6-trideoxyhexopyranoside