Skip to main content

Doxorubicin

ADVERTISEMENT
Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
(7S,9S)-7-(4-amino-5-hydroxy-6-methyl-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 commonly in a solid state, appearing as a crystalline powder.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.00
Boiling point (Celsius)
798.00
Boiling point (Kelvin)
1 071.00
General information
Molecular weight
543.53g/mol
Molar mass
543.5260g/mol
Density
1.6200g/cm3
Appearence

Doxorubicin is a red to orange-red crystalline powder. It is often encountered in a lyophilized (freeze-dried) form when used as a pharmaceutical, providing a vivid and distinctive color.

Comment on solubility

Solubility Characteristics

The compound (7S,9S)-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione presents intriguing solubility properties due to its complex structure. Understanding its solubility behavior can provide insights into its potential applications.

Factors Influencing Solubility:

  • Polarity: The presence of multiple hydroxyl groups significantly increases the polarity of this compound, enhancing its ability to dissolve in polar solvents such as water.
  • Hydrogen Bonding: The amino and hydroxyl groups can form hydrogen bonds, which facilitates solvation in aqueous environments.
  • Size and Structure: The tetracene backbone introduces hydrophobic characteristics, which may limit solubility in non-polar solvents.

Given these aspects, it is likely that this compound is:

  • Soluble in polar solvents (e.g., water, methanol).
  • Less soluble in non-polar solvents (e.g., hexane, benzene).

As with many organic compounds, the solubility of this tetrahydro compound may also be influenced by temperature, concentration, and the presence of other solutes. Conducting specific solubility tests would yield quantitative data that could further elucidate its practical applications in various fields.

Interesting facts

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

This complex and intriguing compound is a member of the tetracene family, a class of polycyclic aromatic hydrocarbons. Known for their fascinating optical and electronic properties, tetracenes are predominantly studied for applications in organic electronics and photonic devices. Here are some compelling aspects:

  • Biosynthetic Pathways: The intricate structure of this compound hints at potential biosynthetic routes that involve both natural and synthetic pathways. Understanding these pathways can lead to advancements in biochemistry and synthetic biology.
  • Medicinal Chemistry: With features such as amino and hydroxy groups, this molecule could exhibit interesting biological activities. Research has shown that similar compounds can possess antibacterial, antifungal, or even anticancer properties, making them significant in the pharmaceutical field.
  • Materials Science: Due to its conjugated system, the compound may show promise in materials science, particularly in developing organic semiconductors, photodetectors, and light-emitting devices. The unique electronic structure enables exciting possibilities for future technologies.
  • Structure-Activity Relationships: The detailed architecture of this compound, with its multiple functional groups, presents an excellent opportunity for studying structure-activity relationships (SAR). This could lead to the design of more effective compounds with targeted biological activities.

As with many complex organic compounds, precursors and synthetic modifications are integral to their research. Continuous study of such compounds not only enhances our understanding of their properties but also pushes the boundaries of innovation in various scientific fields.

Synonyms
(7S,9S)-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
(7S,9S)-7-[(4-amino-5-hydroxy-6-methyl-2-oxanyl)oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
MLS002702107
NSC307241
NSC-307241
NCGC00163543-01
CHEMBL6608
SCHEMBL95415
SCHEMBL3036863
SCHEMBL29692312
CHEBI:124964
HSCI1_000272
NCGC00163543-02
NCI60_000547
SMR001565675
ADR
AB01013751-05
BRD-A56518012-003-01-1
BRD-A56518012-003-02-9
Q27215293
(8s,10s)-10-(4-amino-5-hydroxy-6-methyl-tetrahydro-2h-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione