Skip to main content

Sanguinarine

ADVERTISEMENT
Identification
Molecular formula
C20H15NO4
CAS number
2447-54-3
IUPAC name
(3S,4S,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol
State
State

At room temperature, sanguinarine is typically found as a solid, often in the form of a powder or crystalline structure.

Melting point (Celsius)
218.00
Melting point (Kelvin)
491.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
332.34g/mol
Molar mass
332.3360g/mol
Density
1.3650g/cm3
Appearence

Sanguinarine is typically found as a white crystalline solid or a slightly colored powder. It can also appear in solution as a deep orange or red color, indicating its presence in various organic solvents or when extracted from plant sources.

Comment on solubility

Solubility of (3S,4S,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol

The compound (3S,4S,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol possesses distinct solubility characteristics that are influenced by its complex structure. Factors that determine its solubility include:

  • Polarity: The presence of ionic and polar functional groups, such as the oxido and methoxy groups, can enhance solubility in polar solvents like water.
  • Hydrophobic regions: The hexahydroisoquinoline structure suggests a degree of hydrophobicity, which may reduce solubility in polar solvents while enhancing solubility in non-polar solvents.
  • Temperature and pH: Solubility is often temperature-dependent; thus, alterations in temperature could affect its dissolution rate in specific solvents.

In general, the notion that "like dissolves like" applies here; compounds with a similar polarity to the solvent will solubilize better. For this particular compound:

  1. It is likely to exhibit reasonable solubility in organic solvents such as ethanol or dimethyl sulfoxide (DMSO).
  2. Its solubility in aqueous environments may be limited due to the balance of its hydrophilic and hydrophobic structural elements.

In conclusion, understanding the solubility of this compound is essential for various applications, including pharmaceutical formulations, where solubility can greatly impact bioavailability and therapeutic efficacy.

Interesting facts

Interesting Facts about (3S,4S,4aR,7S,7aR,12bS)-9-Methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol

This unique compound is a fascinating example of the rich diversity found in organic chemistry. With a complex structure, it belongs to the class of isoquinoline derivatives that are noteworthy for their potential pharmaceutical applications. Here are several highlights:

  • Stereochemistry: The designation of multiple stereocenters (3S, 4S, 4aR, 7S, 7aR, 12bS) indicates that this compound can exist in various chiral forms, affecting its biological activity and properties significantly.
  • Natural Compounds: Isoquinolines are often found in plants and have been studied for their physiologically active effects, such as analgesic and antimicrobial properties.
  • Medicinal Chemistry: This compound's structure suggests potential for developing new therapeutics, particularly due to the presence of the methoxy and hydroxy functional groups, which can enhance its pharmacological profile.
  • Importance of Methoxy Groups: The methoxy group is known to enhance lipophilicity and can aid in the transport of the compounds across biological membranes, which is a crucial aspect for drug development.
  • Research Frontier: Compounds like this one are the subject of ongoing research in medicinal chemistry to explore their effects and mechanisms of action, particularly in treating various diseases.

As a chemistry student or a chemist, understanding the synthesis and reactivity of such compounds is essential. Emphasis on the relationship between structure and function often becomes a pivotal theme in drug design and molecular biology. By exploring this compound, one can appreciate the beauty and complexity of the chemical world.