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Qinghaosu (Artemisinin)

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Identification
Molecular formula
C15H22O5
CAS number
63968-64-9
IUPAC name
[1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
State
State

Artemisinin is a solid at room temperature. It is stable under normal temperatures and pressures.

Melting point (Celsius)
156.00
Melting point (Kelvin)
429.15
Boiling point (Celsius)
283.00
Boiling point (Kelvin)
556.15
General information
Molecular weight
282.33g/mol
Molar mass
282.3320g/mol
Density
1.2300g/cm3
Appearence

Artemisinin appears as a white, crystalline powder. It is odorless and tasteless, and due to its crystalline structure, it can appear slightly shiny under light.

Comment on solubility

Solubility of [1,6-Dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] Acetate (C15H22O5)

The solubility of a compound can be influenced by various factors, including its molecular structure and functional groups. In the case of [1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate, we see the presence of multiple polar -OH groups alongside a complex hydrophobic structure.

  • Hydrophilic Components:
    • The two hydroxy (-OH) groups suggest potential for hydrogen bonding, which typically increases solubility in polar solvents like water.
  • Hydrophobic Components:
    • The presence of large hydrocarbon sections in the molecule may lead to a decreased solubility in water, favoring solubility in non-polar organic solvents.

Overall, the solubility behavior can be summed up as follows:

  • Likely soluble in: Alcohols, ethers, and other organic solvents due to hydrophobic characteristics.
  • Potentially less soluble in: Water, stemming from the significant hydrophobic structure, despite the presence of hydrophilic groups.

Therefore, while the hydroxy groups promote interaction with polar environments, the overall solubility in water is expected to be limited due to the propensity of the molecule to interact more favorably with hydrophobic solvents.

Interesting facts

Interesting Facts about 1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl acetate

This unique compound, often revered for its complex structure, showcases an intricate network of functional groups and ring systems. It belongs to a class of compounds known as terpenoids, which are primarily derived from plants and exhibit a range of biological activities. Here are some captivating insights regarding this compound:

  • Natural Origins: Many terpenoids, including this compound, are found in essential oils and resin from various plants. They often play roles in plant defense mechanisms, attracting pollinators, and deterring herbivores.
  • Biological Activity: The structural complexity hints at potential pharmacological properties. Some terpenoids are known for their anti-inflammatory, antimicrobial, and anticancer activities, making compounds like this an area of interest for natural product chemistry.
  • Unique Structural Features: The tetracyclic structure and multiple hydroxyl groups present intriguing possibilities for chemical reactivity and interactions, paving the way for synthetic modification and explorations in medicinal chemistry.
  • Synthesis Challenges: Compounds with such complexity often pose significant challenges during synthesis. Understanding these challenges can deepen insights into synthetic organic chemistry and innovative methodologies.

As researchers continue to explore the potential applications of this compound, its relevance in the field of natural products and medicinal chemistry cannot be understated. The examination of such compounds not only broadens our chemical knowledge but also highlights the intricate relationship between human health and plant-derived substances.

Synonyms
60857-08-1
12-Deoxyphorbol 13-acetate
[1,6-Dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
BDBM86433
BCP29895
CAS_454217
NSC_454217