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Artemisinin

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Identification
Molecular formula
C15H22O5
CAS number
63968-64-9
IUPAC name
9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
State
State

Solid at room temperature, artemisinin is typically encountered in a powdered form.

Melting point (Celsius)
156.00
Melting point (Kelvin)
429.15
Boiling point (Celsius)
290.00
Boiling point (Kelvin)
563.15
General information
Molecular weight
282.33g/mol
Molar mass
282.3320g/mol
Density
1.3500g/cm3
Appearence

Artemisinin is a white crystalline powder. It is a sesquiterpene lactone containing a peroxide bridge, which is unique among antimalarial agents.

Comment on solubility

Solubility of 9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

This compound presents a unique challenge when it comes to solubility due to its complex structure and the presence of multiple functional groups. Here are some key points to consider:

  • Hydrophilicity vs. Hydrophobicity: The presence of hydroxyl (–OH) groups introduces significant hydrophilic character, which typically enhances solubility in polar solvents such as water.
  • Hydrophobic regions: Conversely, the large hydrocarbon skeleton contributes to hydrophobic characteristics, which may limit solubility in aqueous environments.
  • Solvent Selection: This compound is likely to be more soluble in organic solvents like ethanol, dimethyl sulfoxide (DMSO), or acetonitrile, where non-polar parts can interact favorably.
  • Influence of Temperature: Solubility can also be influenced by temperature; increasing temperature often increases the solubility of organic compounds in solvents.

Overall, the solubility of this compound can be described as moderate to variable, depending on the solvent system and external conditions applied. Thus, careful consideration of the solvent medium is crucial for applications involving this compound.

Interesting facts

Interesting Facts about 9,10,22-Trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

This compound is a fascinating example of complex organic chemistry and natural product synthesis. Here are some intriguing aspects:

  • Molecular Complexity: This compound possesses a highly intricate structure, featuring multiple functional groups and a unique arrangement of rings and chains. Its complexity highlights the vast possibilities within organic chemistry.
  • Biological Significance: Compounds with similar structures are often found in natural sources, suggesting potential biological activity. Research indicates that they may exhibit various pharmacological properties, making them of great interest in medicinal chemistry.
  • Research Potential: Chemists are keen on studying compounds like this one for their potential applications in fields such as drug development, where understanding structure-activity relationships can lead to significant therapeutic advancements.
  • Functional Groups: The presence of hydroxyl (-OH) and aldehyde (-CHO) functional groups may impart unique reactivity to the compound, making it suitable for further chemical modifications and reactions.
  • Furan Derivative: The 5-oxo-2H-furan-3-yl substitution suggests potential reactivity associated with furan rings, which are known for their participation in cycloaddition reactions and other pathways in organic synthesis.

As one dives deeper into the world of organic compounds, the exploration of similar complex molecules can unveil new avenues in both theoretical and applied chemistry. The intricacies of their structures often reflect the rich tapestry of molecular interactions found in nature.

Synonyms
NSC650471
SCHEMBL868548
DTXSID40871857
3a,11,11a-Trihydroxy-9,15a-dimethyl-1-(5-oxo-2,5-dihydro-3-furanyl)icosahydro-7aH,13aH-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-13a-carbaldehyde
3a,11,11a-Trihydroxy-9,15a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-7aH,13aH-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-13a-carbaldehyde