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Vincristine

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Identification
Molecular formula
C46H56N4O10
CAS number
57-22-7
IUPAC name
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
State
State

At room temperature, vincristine is in a solid state, typically prepared as a sulfate salt for aqueous solutions used in clinical settings. It is not volatile and needs to be dissolved or prepared as a solution for usage.

Melting point (Celsius)
218.00
Melting point (Kelvin)
491.15
Boiling point (Celsius)
540.00
Boiling point (Kelvin)
813.15
General information
Molecular weight
824.98g/mol
Molar mass
824.9840g/mol
Density
1.3400g/cm3
Appearence

Vincristine appears as a white to off-white crystalline powder. It is typically available as a sulfate salt for medical use. The powder is practically odorless and is commonly used in solution form for intravenous administration.

Comment on solubility

Solubility Analysis of Methyl (1R,15S,17R,18R,19S,20S)-6,18-Dimethoxy-17-[3-(3,4,5-Trimethoxyphenyl)Prop-2-Enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate

The solubility of chemical compounds can often provide essential insights into their behavior in various environments. For the compound methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate, the solubility can be influenced by several intricate factors:

  • Polarity: The presence of multiple methoxy groups suggests that it could exhibit moderate polarity, impacting its solubility in polar solvents like water.
  • Hydrophobic Regions: The dodecahydroyohimban structure implies a significant hydrophobic character that may diminish water solubility but enhance solubility in organic solvents such as ethanol or dichloromethane.
  • Functional Groups: The carboxylate group (-COO-) may improve its solubility in alkaline aqueous solutions compared to neutral or acidic conditions.
  • Temperature and pH: Changes in temperature and pH can also significantly affect solubility, with higher temperatures generally increasing solubility for organic compounds.

In summary, while the exact solubility can vary based on the specific conditions and concentration, this compound is likely to be:

  • Slightly soluble in water
  • Soluble in organic solvents
  • More soluble when deprotonated in alkaline conditions
Thus, understanding the solubility characteristics of this compound is crucial for applications in pharmaceutical and chemical research.

Interesting facts

Interesting Facts about Methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

This complex compound, often referred to as a derivative of yohimbine, is noteworthy for its intricate structure and potential uses. Here are some fascinating aspects of it:

  • Natural Occurrence: Yohimbine itself is derived from the bark of the Yohimbe tree, native to Central and Western Africa, where it is used in traditional medicine.
  • Modifications: The presence of multiple methoxy groups in this compound enhances its solubility and biological activity, making it a subject of interest in pharmaceutical research.
  • Potential Applications: Compounds like this one are being studied for various therapeutic effects, including aphrodisiac properties and potential use in weight loss and anxiety treatment.
  • Stereochemistry: With multiple stereogenic centers, the exact 3D arrangement of atoms plays a crucial role in its bioactivity. As a result, isomeric variations can lead to significantly different effects in biological systems.
  • Advanced Synthesis: The synthesis of such compounds can be quite challenging, involving several steps of organic reactions like selective methylation, esterification, and elaborate purification methods.

As a scientist or chemistry student, delving into the structure and properties of this compound lends insight not only into organic synthesis but also into the complexities of drug design and pharmacology. While research is ongoing, the multifunctional nature of this compound positions it as a potential candidate for more comprehensive studies that could lead to valuable biomedical applications.

Synonyms
Reserpinine
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Prestwick0_000568
Prestwick1_000568
SPBio_002575
CHEMBL3182071
DB01180
Q27164665
(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester