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Juglone

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Identification
Molecular formula
C10H6O3
CAS number
481-39-0
IUPAC name
7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione
State
State

Juglone is typically found in a solid crystalline form at room temperature.

Melting point (Celsius)
155.00
Melting point (Kelvin)
428.15
Boiling point (Celsius)
465.00
Boiling point (Kelvin)
738.15
General information
Molecular weight
174.15g/mol
Molar mass
174.1490g/mol
Density
1.6940g/cm3
Appearence

Juglone is a yellow crystalline solid with an orange cast. It is known for its strong staining properties and is often used as a dye. It has a distinctive coloration that may vary under different lighting conditions.

Comment on solubility

Solubility of 7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione

The solubility of 7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione can be characterized as follows:

  • Solvent Dependence: This compound exhibits varying solubility in different solvents. It tends to dissolve better in polar solvents due to the presence of hydroxyl (-OH) groups, which can engage in hydrogen bonding.
  • Polarity Effects: The presence of multiple functional groups, including methoxy (-OCH3) and hydroxyl (-OH), increases the polarity of the molecule, enhancing its solvation in polar environments.
  • Temperature Influence: As with many organic compounds, solubility may increase with temperature. Heating can help disrupt intermolecular interactions and increase the dissolution rate.
  • pH Sensitivity: The solubility may also be affected by the pH of the solution, especially because of the acidic and basic nature of the functional groups present.

In summary, 7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione is likely to show good solubility in polar solvents while demonstrating sensitivity to both temperature and pH variations. As a general rule, "like dissolves like," hence mimicking the solvent properties will yield the best solubility results.

Interesting facts

7-Acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione: An Insight into a Unique Compound

This compound, 7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione, belongs to the fascinating class of organic compounds known as naphthoquinones. Naphthoquinones are characterized by their rich coloring and diverse reactivity, which opens the door to numerous applications in various fields.

Interesting Facts:

  • Biological Activity: Compounds in the naphthoquinone family are known for their significant biological activities, including *antimicrobial*, *antioxidant*, and *anticancer* properties. Research indicates that they can interact with cellular processes, which makes them important in pharmaceutical development.
  • Synthesis: The synthesis of such complex molecules typically involves advanced organic methods, including multi-step reactions. This compound showcases how chemists can manipulate structures to achieve desired biological effects.
  • Natural Occurrence: Naphthoquinones are found in various plants and fungi, suggesting that they play crucial roles in ecological interactions, such as defending against herbivores or pathogens.
  • Versatility: This compound's structure signifies potential utility in *dyes*, *pigments*, and *coatings*, thanks to its vibrant color and stability.
  • Research Potential: The ongoing research surrounding naphthoquinones emphasizes the need for deeper exploration into their mechanisms of action and potential therapeutic applications.

This fascinating compound not only exemplifies the intricate beauty of organic chemistry but also serves as a reminder of the vast potential residing in nature’s own creations. As research continues, compounds like 7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione might unveil new pathways for innovation in healthcare and materials science.

Synonyms
JAVANICIN
476-45-9
Javanicin (Fusarium)
5,8-Dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione
HSDB 3501
YNR51WFW2R
BRN 2296055
JAVANICIN [MI]
JAVANICIN [HSDB]
3-Acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-1,4-naphthoquinone
5,8-Dihydroxy-6-methoxy-3-(2-oxopropyl)-1,4-naphthalenedione
1,4-Naphthalenedione, 5,8-dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-
1,4-Naphthoquinone, 3-acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-
4-08-00-03646 (Beilstein Handbook Reference)
5,8-Dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-1,4-naphthalenedione
1,4-NAPHTHALENEDIONE, 7-ACETONYL-5,8-DIHYDROXY-2-METHOXY-6-METHYL-
1,4-NAPHTHALENEDIONE, 5,8-DIHYDROXY-2-METHOXY-6-METHYL-7-(2-OXOPROPYL)-
DTXCID401391608
dtxsid40963882
5,8-dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)naphthalene-1,4-dione
UNII-YNR51WFW2R
fusarium
SCHEMBL3147213
CHEMBL1224810
DTXSID30871664
CHEBI:209872
AKOS040745888
Q27294612
7-acetonyl-5,8-dihydroxy-2-methoxy-6-methyl-naphthalene-1,4-dione