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Sterigmatocystin

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Identification
Molecular formula
C18H12O6
CAS number
10048-13-2
IUPAC name
(1S,2R,3S,7R,9R,10R,11S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
State
State

At room temperature, sterigmatocystin is a solid. Its crystalline form is stable under normal atmospheric conditions, and it does not readily sublimate or evaporate.

Melting point (Celsius)
246.00
Melting point (Kelvin)
519.15
Boiling point (Celsius)
405.00
Boiling point (Kelvin)
678.15
General information
Molecular weight
324.30g/mol
Molar mass
324.3000g/mol
Density
1.4900g/cm3
Appearence

Sterigmatocystin appears as a yellow to orange crystalline solid. It is known for its bright coloration, which is typical for many compounds belonging to the class of polyketides. These crystals can have a distinct facet structure, similar to other crystalline organic compounds.

Comment on solubility

Solubility of (1S,2R,3S,7R,9R,10R,11S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one

The solubility of the compound (1S,2R,3S,7R,9R,10R,11S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one can be influenced by several factors due to its complex molecular structure:

  • Polarity: The presence of multiple hydroxyl (-OH) groups greatly enhances the compound's polarity, making it more likely to dissolve in polar solvents such as water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with water molecules increases solubility. Each hydroxyl group can participate in these interactions.
  • Hydrophobic components: Despite the polar characteristics, any hydrophobic regions present in the compound could limit solubility in polar solvents. These components may require non-polar solvents for effective dissolution.
  • Temperature: As with many compounds, increased temperature can facilitate solubility due to enhanced molecular motion, aiding solvation processes.

In conclusion, while the compound exhibits characteristics that suggest a general tendency towards solubility in polar solvents due to its hydroxy groups, specific solubility can vary based on external conditions and the solvent utilized. Understanding these aspects is essential for practical applications and further studies.

Interesting facts

Interesting Facts about (1S,2R,3S,7R,9R,10R,11S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one

This complex compound features a fascinating structure that has garnered interest in the field of organic chemistry. Here are some intriguing aspects:

  • Stereochemistry: The compound's chiral centers play a critical role in its biological activity. With its precise stereochemical configuration, it can interact with biological systems with a high level of specificity.
  • Structural Complexity: This molecule exhibits a spirocyclic structure, consisting of various rings fused together. Such spirocycles are often found in natural products and can lead to unexpected chemical behaviors.
  • Functional Groups: It possesses multiple hydroxy groups, suggesting potential applications in pharmaceuticals and biochemistry. These functional groups could participate in hydrogen bonding, influencing the compound’s reactivity and solubility.
  • Mechanistic Insights: Studying compounds with complex stereochemistry like this one can provide insights into reaction mechanisms, particularly in organic synthesis and natural product isolation.
  • Potential Applications: The unique structure of this compound might be useful in drug development, as many biologically active molecules display similar configurations. Research is ongoing to explore its possible therapeutic effects.

As a note from a chemistry student, one might find that compounds like this challenge our understanding of molecular interactions and the importance of 3D configurations in biological systems. Exploring such intricate molecules can open doors to innovative research pathways and novel applications in various scientific fields.

Conclusion

In summary, (1S,2R,3S,7R,9R,10R,11S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one represents the beauty and complexity of organic chemistry, offering a prime example of how specialized structures correlate with potential biological activity. The ever-deepening investigation into such compounds continues to enhance our understanding of chemistry and its applications.

Synonyms
(1S,2R,3S,7R,9R,10R,11S)-3,10,11-Trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
SCHEMBL30319
nivalenol (stereochemistry not fully defined)
Q409569
(3alpha,4beta,7alpha)-3,4,7,15-tetrahydroxy-12,13-epoxytrichothec-9-en-8-one
(1S,2R,3S,7R,9R,10R,11S,12R)-3,10,11-Trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one