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Artemisinin

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Identification
Molecular formula
C15H22ClNO5
CAS number
63968-64-9
IUPAC name
21-chloro-10-isopropenyl-15,16,33,33-tetramethyl-24-methylene-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
State
State

At room temperature, artemisinin is typically in a solid state.

Melting point (Celsius)
156.00
Melting point (Kelvin)
429.15
Boiling point (Celsius)
110.00
Boiling point (Kelvin)
383.15
General information
Molecular weight
282.34g/mol
Molar mass
282.3330g/mol
Density
1.2900g/cm3
Appearence

Artemisinin is a white crystalline powder. It is known for its characteristic appearance under certain lighting conditions, often forming slender, needle-like crystals when observed closely.

Comment on solubility

Solubility of 21-chloro-10-isopropenyl-15,16,33,33-tetramethyl-24-methylene-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol

The solubility of the compound with the formula C15H22ClNO5 presents notable features influenced by its complex structure. Here are some key points to consider:

  • Polarity: The presence of chlorine (Cl) and nitrogen (N) atoms enhances the polarity of the molecule, likely making it more soluble in polar solvents such as water.
  • Hydroxyl Groups: With multiple hydroxyl (–OH) groups due to the triol functionality, the compound can form hydrogen bonds with water, contributing significantly to its solubility.
  • Hydrophobic Features: However, the significant non-polar hydrocarbon portions may hinder its full solubility in highly polar environments, suggesting a potential for limited solubility in water.
  • Solvent Compatibility: The compound may exhibit better solubility in organic solvents like ethanol or acetone, where hydrophobic interactions would predominate.

In summary, while the compound may exhibit appreciable solubility in polar solvents due to its functional groups, its overall solubility may still be somewhat restricted by its larger hydrophobic structure. When working with such compounds, it is crucial to consider both the polar and non-polar aspects of their solubility profiles.

Interesting facts

21-chloro-10-isopropenyl-15,16,33,33-tetramethyl-24-methylene-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol

This intriguing compound, known for its complex structure and unique properties, is a remarkable example of a terpenoid. To better understand its significance, here are some interesting facts:

  • Structural Complexity: The compound features a highly intricate arrangement of rings and functional groups, making it a subject of interest in synthetic organic chemistry.
  • Biological Interest: Many terpenoids like this compound are known to exhibit various biological activities such as anti-inflammatory and antimicrobial properties.
  • Chlorine Substitution: The presence of a chlorine atom in its structure often influences the reactivity and interaction of the compound with biological systems.
  • Synthetic Applications: Its structural features inspire chemists to develop new methods for synthesizing complex molecules, paving the way for innovative pharmaceuticals and agrochemicals.
  • Potential Uses: This compound may have potential applications in drug development due to its unique properties, which can be explored for therapeutic benefits.

As noted by researchers, the exploration of such compounds not only enhances our understanding of chemistry but also contributes to the discovery of new materials with practical applications. Its rich molecular architecture truly demonstrates the beauty and complexity that can arise in chemical compounds.

Synonyms
Tremortin A
Penitrem A, Penicillium paxilli
21-Chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
SCHEMBL353318
DB-041819