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Picrotoxin

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Identification
Molecular formula
C30H34O13
CAS number
124-87-8
IUPAC name
[(2S,4R,6R,7R,11S,14S,16R)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-14-yl] acetate
State
State
Picrotoxin is generally found as a solid at room temperature, typically in the form of needles or a crystalline powder.
Melting point (Celsius)
199.00
Melting point (Kelvin)
472.00
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.00
General information
Molecular weight
602.55g/mol
Molar mass
602.5460g/mol
Density
1.3800g/cm3
Appearence

Picrotoxin appears as colorless needles or a white crystalline powder. It is typically odorless and has a very bitter taste.

Comment on solubility

Solubility of [(2S,4R,6R,7R,11S,14S,16R)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-14-yl] acetate

This compound showcases interesting solubility characteristics, primarily influenced by its complex structure. Given the intricate nature of this molecular composition, one can identify several key factors that underline its solubility behavior:

  • Polarity: The presence of various functional groups, such as esters and keto groups, suggests that the compound may exhibit some polar characteristics, potentially enhancing its solubility in polar solvents.
  • Hydrophobic Regions: Conversely, the hydrophobic portions of the compound due to the aliphatic chains might result in limited solubility in aqueous solutions, making it more soluble in organic solvents.
  • pH Sensitivity: The solubility may also vary with changes in pH, where ionization of certain groups can either increase or decrease solubility in water.

Ultimately, the solubility of this compound can be characterized as:

  1. Moderately soluble in polar organic solvents such as ethanol and methanol.
  2. Less soluble in water due to hydrophobic interactions.
  3. Potentially soluble in non-polar solvents, aligning with its hydrophobic characteristics.

In conclusion, the solubility of [(2S,4R,6R,7R,11S,14S,16R)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-14-yl] acetate exemplifies a balance between polar and non-polar characteristics, where practical testing in different media is essential for exact solubility assessments.

Interesting facts

Interesting Facts About the Compound

This compound is a fascinating example of natural products and their complex structures. Known for its unique stereochemistry, it contains multiple chiral centers, making it an intriguing subject of study for chemists interested in the production and manipulation of chiral molecules.

Biological Significance

  • Natural Origins: This compound is often derived from natural sources, playing a vital role in various biological processes.
  • Pharmaceutical Applications: Compounds with complex structures like this are often investigated for their potential therapeutic effects, such as anti-inflammatory or antimicrobial properties.
  • Insect Attraction: Some components of natural products are utilized in developing insect attractants, showcasing their ecological importance.

Synthesis and Application

Researchers have developed synthetic methods for such compounds to facilitate their study and use in medicinal chemistry. The complex nature of this molecule may lead to interesting findings in:

  • Synthetic Chemistry: Exploring new synthetic routes can provide insights into reaction mechanisms.
  • Drug Development: The potential to modify the structure slightly can lead to variations with improved efficacy or reduced side effects.

Challenges and Explorations

Studying compounds like this also poses challenges:

  • Stereochemical Complexity: The number of stereocenters makes it challenging to synthesize and purify.
  • Characterization Issues: Understanding its full properties requires sophisticated analytical techniques.

In conclusion, this compound serves as a prime example of the intricate connections between natural chemistry and synthetic applications. As researchers continue to explore its properties, we may uncover new possibilities that could impact various fields, from pharmacology to environmental science.

Synonyms
Acetylresibufogenin
Resibufogenin acetate
NSC 135688
5-beta-BUFA-20,22-DIENOLIDE, 14,15-beta-EPOXY-3-beta-HYDROXY-, ACETATE
Bufa-20,22-dienolide, 3-(acetyloxy)-14,15-epoxy-, (3-beta,5-beta,15-beta)-
Resibufogenin acetate (6CI)