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Doxorubicin

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Identification
Molecular formula
C27H29NO11
CAS number
23214-92-8
IUPAC name
7-(4-amino-6-methyl-5-tetrahydropyran-2-yloxy-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
State
State

At room temperature, doxorubicin is typically in a solid state. The compound is commonly supplied in a powder form for reconstitution with an appropriate solvent for clinical use.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.20
Boiling point (Celsius)
694.20
Boiling point (Kelvin)
967.40
General information
Molecular weight
543.52g/mol
Molar mass
543.5200g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin typically appears as a red-orange, crystalline powder. It is commonly used in a hydrochloride salt form for medical applications, which is usually presented in a red to orange-red solution when dissolved in water or other solvents suitable for intravenous administration.

Comment on solubility

Solubility of 7-(4-amino-6-methyl-5-tetrahydropyran-2-yloxy-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione (C27H29NO11)

The solubility of this compound exhibits several intriguing characteristics, reflecting both its complex structure and the interactions at play. Here are the key points to consider regarding its solubility:

  • Polarity: The presence of multiple hydroxyl groups and an amino group suggests that the compound should have some degree of polarity, which could enhance its solubility in polar solvents like water.
  • Hydrogen Bonding: The -OH groups may facilitate hydrogen bonding with solvent molecules, thereby increasing solubility in suitable environments.
  • Solvent Interactions: It may dissolve more readily in organic solvents such as ethanol or methanol due to its nonpolar tetracene core which is compatible with such solvents.
  • Crystallinity: The structural complexity might result in a higher likelihood of crystallization, which could hinder solubility in some cases.
  • Temperature Effect: Like many organic compounds, solubility may increase with temperature, allowing for a better interaction between the solute and solvent.

Overall, the compound’s solubility can be described as variable and highly dependent on the surrounding conditions, including the choice of solvent, temperature, and the molecular interactions that take place. Thus, a thorough understanding requires experimental validation to establish precise solubility data. As stated, "Solubility behaviour is best characterized by experimental inquiry."

Interesting facts

Interesting Facts about 7-(4-amino-6-methyl-5-tetrahydropyran-2-yloxy-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

This compound, known for its intricate structure, is a fascinating example of organic chemistry’s ability to synthesize complex materials with potential biological applications. The presence of multiple functional groups and a unique framework provides this molecule with intriguing properties.

Key Highlights:

  • Diverse Functional Groups: This compound features several functional groups, including aminocoumarins, phenolic hydroxyls, and methoxy groups, each contributing to its biological and chemical properties.
  • Potential Pharmacological Applications: Given its structure, this compound may exhibit interesting biological activity, potentially serving as a lead in drug discovery particularly in the realm of anticancer or antimicrobial agents.
  • Complexity of Synthesis: The synthesis of this compound involves intricate multi-step reactions, showcasing the creativity and precision required in organic synthesis. It presents an excellent challenge for those studying synthetic methods.
  • Backbone Structure: The tetracene backbone adds a layer of stability and rigidity to the molecule, which is often crucial in the development of materials used in electronics and photonics.
  • Natural Product Hybrids: The incorporation of tetrahydropyran rings highlights its potential as a natural product hybrid, combining elements from different chemical realms.

Overall, the diverse structural features and potential applications make 7-(4-amino-6-methyl-5-tetrahydropyran-2-yloxy-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione a significant compound that is ripe for further study.

Synonyms
pirarubicin
72496-41-4
7-[4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
SCHEMBL13421276
DTXSID20860941
LS-15332
3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-oxan-2-ylhexopyranoside