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Arecoline

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Identification
Molecular formula
C8H13NO2
CAS number
300-08-3
IUPAC name
[(1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methyl-butanoate
State
State
Arecoline is in a liquid state at room temperature, usually appearing as an oily liquid.
Melting point (Celsius)
0.00
Melting point (Kelvin)
273.15
Boiling point (Celsius)
216.50
Boiling point (Kelvin)
489.70
General information
Molecular weight
155.23g/mol
Molar mass
155.2330g/mol
Density
1.0108g/cm3
Appearence
Arecoline is typically a colorless to a pale yellow oily liquid. Its appearance can vary slightly, but it generally maintains a clear and oily consistency.
Comment on solubility

Solubility Insights

The solubility of the compound [(1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methyl-butanoate can be intricate due to its complex structure. A few key considerations regarding its solubility include:

  • Polarity: Given its multiple hydroxyl groups, it is likely that this compound exhibits considerable polarity, which generally enhances solubility in polar solvents like water.
  • Functional Groups: The presence of both pyrrolizine and hydroxyethyl groups suggests that it may form hydrogen bonds, contributing positively to its solubility.
  • Temperature Dependency: Like many organic compounds, its solubility could increase with a rise in temperature, allowing for better dissolution in solvents.
  • pH Sensitivity: The ionization of certain functional groups at varying pH levels may lead to changes in solubility, which is important for applications in biological systems.

In summary, while the exact solubility of this compound would require experimental determination, we can anticipate that its structural attributes would favor solubility in suitable solvents, particularly in aqueous environments. "Understanding the solubility profile is essential for predicting behavior in both natural and industrial processes." This compound's unique framework may offer versatility in its applications, strongly tied to how well it dissolves in different media.

Interesting facts

Interesting Facts about [(1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methyl-butanoate

This compound, with its intricate structure, offers a fascinating glimpse into the world of organic chemistry and its potential applications. Here are some intriguing highlights:

  • Complex Structure: The compound belongs to a class known as pyrrolizidine alkaloids, which are known for their diverse biological activities. Its multiple stereocenters give rise to a rich array of possible isomers, making synthesis and characterization particularly challenging.
  • Biological Significance: Compounds like this one have been studied for their pharmacological properties, including potential roles in anti-cancer and anti-inflammatory therapies. Their unique configurations can lead to distinct biological responses.
  • Chirality Matters: The presence of stereocenters makes chirality a critical aspect of this compound. Different enantiomers may exhibit varied effects in biological systems, emphasizing the importance of stereochemistry in drug design.
  • Natural Occurrence: Many pyrrolizidine alkaloids are found in plants, particularly in the Boraginaceae family. This compound may hint at natural pathways for its formation and potential therapeutic uses derived from plant sources.
  • Use in Research: Chemists are keen to investigate this compound as it can serve as a scaffold for developing new pharmaceutical agents. Researchers often explore the modification of such compounds to enhance their biological activity.

In summary, the complexity of [(1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methyl-butanoate embodies the intricate interplay between structure and function in the world of organic chemistry. Each facet of this molecule opens up new avenues for exploration and discovery.

Synonyms
Trachelanthine
510-19-0
Trachelanthamine N-oxide
[(1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl]methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7aS)-hexahydro-4-oxido-1H-pyrrolizin-1-yl)methyl ester, (2S,3R)-
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (hexahydro-1H-pyrrolizin-1-yl)methyl ester, N-oxide, (1R-(1-alpha(2S*,3R*),7a-alpha))-
((1S,8S)-4-oxido-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-4-ium-1-yl)methyl (2R)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
Trachelanthamine oxide
(1R,7aS)-1-[[[(2S,3R)-2,3-Dihydroxy-2-isopropylbutanoyl]oxy]methyl]hexahydro-1H-pyrrolizine 4-oxide
AKOS040760030
TS-10106
(1S,7AS)-1-((((2R)-2,3-dihydroxy-2-isopropylbutanoyl)oxy)methyl)hexahydropyrrolizine 4(1H)-oxide
(1S,7aS)-1-({[(2R)-2,3-dihydroxy-2-isopropylbutanoyl]oxy}methyl)-hexahydro-1H-pyrrolizin-4-ium-4-olate