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Paclitaxel

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Identification
Molecular formula
C47H51NO14
CAS number
33069-62-4
IUPAC name
[4,12-diacetoxy-15-(3-benzamido-2-hydroxy-3-phenyl-propanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
State
State

Paclitaxel is a solid at room temperature.

Melting point (Celsius)
213.00
Melting point (Kelvin)
486.20
Boiling point (Celsius)
785.50
Boiling point (Kelvin)
1 058.70
General information
Molecular weight
853.91g/mol
Molar mass
853.9060g/mol
Density
1.4330g/cm3
Appearence

Paclitaxel is a white to off-white crystalline powder. It is practically insoluble in water, but soluble in dimethyl sulfoxide, and miscible with ethanol and acetone. It has a characteristic odour.

Comment on solubility

Solubility of [4,12-diacetoxy-15-(3-benzamido-2-hydroxy-3-phenyl-propanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate (C47H51NO14)

The solubility of complex organic compounds like [4,12-diacetoxy-15-(3-benzamido-2-hydroxy-3-phenyl-propanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate is influenced by several factors:

  • Polarity: Given the presence of multiple functional groups, the polarity of the molecule can greatly affect solubility in polar solvents like water.
  • Hydrogen Bonding: The -OH groups suggest potential for intramolecular and intermolecular hydrogen bonding, which can enhance solubility in certain solvents.
  • Molecular Size: With a large molecular weight (C47H51NO14), the spatial configuration can create steric hindrance, potentially impacting solubility.
  • Solvent Interaction: Solubility may be better in organic solvents such as ethanol or acetone compared to aqueous solutions.

As a general rule of thumb, "like dissolves like," meaning that polar compounds tend to be soluble in polar solvents, while non-polar compounds are better dissolved in non-polar solvents. In conclusion, the solubility of this intricate compound likely varies across solvent types, and experimental data would provide the most accurate assessment.

Interesting facts

Interesting Facts about [4,12-diacetoxy-15-(3-benzamido-2-hydroxy-3-phenyl-propanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

This compound is a fascinating example of a complex organic molecule with intricate structural features. Here are some engaging highlights:

  • Structural Complexity: The molecular structure features multiple functional groups and intricate ring systems, indicative of its potential reactivity and biological activity.
  • Applications: Compounds like this can be of interest in medicinal chemistry, particularly for their potential use as pharmaceuticals or in drug design due to their unique structural properties.
  • Biological Relevance: The presence of phenyl and hydroxyl groups suggests possible interactions with biological systems, which can lead to interesting avenues for research in pharmacology.
  • Natural Products Chemistry: This compound reminds us of the importance of natural product breakthroughs in drug discovery. Many complex molecules are derived from natural sources, showcasing the intricacies of nature’s organic chemistry.
  • Multifunctionality: The multiple acetate and hydroxy groups can impart various physical and chemical properties, potentially leading to multifunctionality in its applications.

As evidenced by this compound, the world of organic chemistry is rich with opportunities for discovery and innovation. The process of studying and synthesizing such complex molecules not only enhances our understanding of chemical behaviors but also aids in the development of new therapeutic agents. Indeed, the adage "One compound can open a multitude of doors" rings particularly true in the realm of chemical research!

Synonyms
7-Epi Paclitaxel
379688-61-6
NSC 125973
608129-32-4
Paclitaxel-[d5]
Neuro_000060
CHEMBL100910
SCHEMBL18389589
CHEBI:91594
DTXSID60860480
RCINICONZNJXQF-UHFFFAOYSA-N
HMS3267I12
BCP13612
LSM-1400
NSC358882
STL451051
STL454988
AKOS037482516
NSC-358882
NCGC00016048-03
LS-15477
SY016928
BRD-A23723433-001-01-2
Q27163425
7,11-Methano-5H-cyclodeca(3,4)benz(1,2-b)oxete, benzenepropanoic acid deriv.
7-epi-Paclitaxel pound>>7-Epi-Taxol pound>>7-Epipaclitaxel pound>>Paclitaxel Impurity E
[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10.0^{4,7]heptadec-13-en-2-yl] benzoate
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10.0^{4,7]heptadec-13-en-2-yl] benzoate
[4,12-diacetyloxy-15-(3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
[diacetoxy-(3-benzamido-2-hydroxy-3-phenyl-propanoyl)oxy-dihydroxy-tetramethyl-oxo-[?]yl] benzoate
4,10-bis(acetyloxy)-1,7-dihydroxy-13-({2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
4,10-Bis(acetyloxy)-13-[(3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
N-[3-({4,10-bis(acetyloxy)-1,7-dihydroxy-9-oxo-2-[(phenylcarbonyl)oxy]-5,20-epoxytax-11-en-13-yl}oxy)-2-hydroxy-3-oxo-1-phenylpropyl]benzenecarboximidic acid
Tax-11-en-9-one, 5.beta.,20-epoxy-1,2.alpha.,4,7.beta.,10.beta.,13.alpha.- hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine