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Methyl yohimbate

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Identification
Molecular formula
C22H28N2O3
CAS number
40077-57-4
IUPAC name
methyl (1S,18S,19R)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
State
State

Methyl yohimbate is a solid at room temperature. It is typically found as a crystalline substance.

Melting point (Celsius)
238.50
Melting point (Kelvin)
511.65
Boiling point (Celsius)
559.40
Boiling point (Kelvin)
832.55
General information
Molecular weight
356.47g/mol
Molar mass
356.4530g/mol
Density
1.1500g/cm3
Appearence

Methyl yohimbate is typically a white crystalline solid. It has a characteristic appearance of fine crystals or powder.

Comment on solubility

Solubility of Methyl (1S,18S,19R)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate (C22H28N2O3)

The solubility of methyl (1S,18S,19R)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate is influenced by its complex molecular structure, which contains multiple functional groups. Here are some key aspects to consider:

  • Polar and Non-Polar Characteristics: The presence of hydroxyl groups (–OH) in the structure increases its polarity, thereby enhancing its potential solubility in polar solvents such as water.
  • Solvents & Solubility: It is generally soluble in organic solvents such as methanol, ethanol, and DMSO due to its hydrophobic hydrocarbon chain.
  • Hydrogen Bonding: The ability to form hydrogen bonds through the hydroxyl and carboxyl groups suggests that this compound could exhibit better solubility in aqueous solutions compared to less polar counterparts.
  • Concentration Effects: Like many organic compounds, the solubility may vary significantly with temperature and concentration, often increasing with higher temperatures.

In conclusion, while the solubility of methyl (1S,18S,19R)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate is likely to be favorable in specific solvents, it is important to be mindful of the solvent polarity and temperature conditions that can impact its overall solubility profile.

Interesting facts

Interesting Facts about Methyl (1S,18S,19R)-18-Hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate

This fascinating compound belongs to the family of yohimban alkaloids, which are primarily derived from the bark of the Pausinystalia yohimbe tree, a plant native to Western Africa. Yohimbine, the most well-known derivative, has garnered attention for its uses in various therapeutic areas. Here are some interesting aspects of this unique compound:

  • Therapeutic Potential: Yohimbine has been studied for its potential in treating erectile dysfunction and for its use as an aphrodisiac. Research continues into the broader implications for anxiety relief and mood enhancement.
  • Mechanism of Action: This compound operates primarily as an α2-adrenergic antagonist, increasing sympathetic outflow, which can enhance blood flow and potentially improve sexual function.
  • Chemical Structure: The compound features a complex multi-ring structure that contributes to its biological activity. Its stereochemistry enhances its pharmacological effects, making specific stereoisomers highly effective.
  • Historical Context: Traditional uses of yohimbe bark include the treatment of fatigue and as a tribal aphrodisiac. The exploration of yohimban compounds dates back to ancient times, showcasing the intersection of botanical knowledge and pharmacology.

As a scientist or chemistry student, exploring the properties of methyl (1S,18S,19R)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate offers a window into a rich field of study that bridges natural products and pharmacology. Understanding the nuances of such compounds can provide insights into drug development and the quest for complementary therapies in modern medicine. With ongoing research, yohimban alkaloids continue to unveil secrets that may lead to innovative health solutions.