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Paclitaxel

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Identification
Molecular formula
C47H51NO14
CAS number
33069-62-4
IUPAC name
[(7R,8S)-11-(hexylamino)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
State
State
Solid
Melting point (Celsius)
213.00
Melting point (Kelvin)
486.15
Boiling point (Celsius)
375.00
Boiling point (Kelvin)
648.15
General information
Molecular weight
853.91g/mol
Molar mass
853.9060g/mol
Density
1.4321g/cm3
Appearence
Paclitaxel is a white to off-white crystalline powder. It is practically insoluble in water and very soluble in dichloromethane and ethanol.
Comment on solubility

Solubility Profile

The solubility of the compound [(7R,8S)-11-(hexylamino)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate exhibits several intriguing characteristics due to its complex structure.

Key Factors Influencing Solubility:

  • Molecular Structure: The presence of various functional groups such as the carbamate, methoxy, and amine significantly affects solubility.
  • Polarity: The compound contains polar bonds, which can enhance its solubility in polar solvents like water.
  • Hydrocarbon Chain: The hexylamine group introduces hydrophobic characteristics, which may reduce solubility in polar solvents while increasing solubility in organic solvents.
  • pH Sensitivity: The solubility may vary with pH changes, as carbamate functionalities may ionize depending on the environment.

Overall, it is essential to test the solubility in various solvents to determine the most suitable conditions for its use. As a general consideration, compounds with significant hydrophobic regions tend to display lower solubility in water but may dissolve well in non-polar solvents. As one expert would say, "The solubility is a delicate balance of structure and the surrounding environment." Understanding these relationships will provide insights into its practical applications in chemical processes.

Interesting facts

Interesting Facts about [(7R,8S)-11-(hexylamino)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

This compound is a fascinating example of organic chemistry and showcases the complexity of molecular structures that can exist within a single molecule. Its unique configuration includes:

  • Tetracyclic Framework: The compound features a tetracyclic structure, which can lead to a variety of interesting properties and reactivities due to the rigidity and steric hindrance provided by the rings.
  • Specification of Stereochemistry: The notation (7R,8S) indicates its chiral centers, which play a vital role in the biological activity of the compound, often influencing how the molecule interacts with enzymes, receptors, and other biomolecules.
  • Functional Groups: The presence of a carbamate functional group is significant for its potential applications in drug design and development, providing a site for various chemical reactions.

Furthermore, this compound is of particular interest in the field of medicinal chemistry. Compounds with similar complex structures may be investigated for various therapeutic effects, including:

  • Anticancer Activity: Compounds with conjugated double bonds can exhibit strong interactions with DNA, which is crucial for the development of antitumor drugs.
  • Antimicrobial Properties: The nitrogen-containing dioxo components can enhance the bioactivity against a range of microbial pathogens.
  • Neuroprotective Effects: The hexylamino group may play a role in enhancing solubility and permeability across biological membranes, potentially aiding in neuroprotective applications.

This compound not only illustrates the incredible diversity found within chemical species but also serves as a reminder of the intricate dance between structure and function in the realm of medicinal chemistry. As scientists continue to explore compounds like this for therapeutic potentials, they remind us of the profound connection between chemistry and life.

Synonyms
DTXSID00933187
[6-(Hexylamino)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl hydrogen carbonimidate