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Juglone

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Identification
Molecular formula
C10H6O3
CAS number
481-39-0
IUPAC name
5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyl-octacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone
State
State
Juglone is typically found as a crystalline solid at room temperature, appearing as yellow-brown crystals.
Melting point (Celsius)
155.00
Melting point (Kelvin)
428.15
Boiling point (Celsius)
600.00
Boiling point (Kelvin)
873.15
General information
Molecular weight
174.15g/mol
Molar mass
174.1450g/mol
Density
0.8300g/cm3
Appearence

Juglone appears as a yellow crystalline solid. It may form into bright orangish-yellow needles when crystallized. The compound can darken upon exposure to air due to oxidation.

Comment on solubility

Solubility of 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyl-octacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

The solubility of this intricate compound is a fascinating subject due to its complex structure and numerous functional groups. Understanding its solubility can offer insights into its chemical behavior and potential applications. Here are some key considerations:

  • Hydroxyl Groups: The presence of multiple hydroxyl (–OH) groups generally enhances solubility in polar solvents, such as water. This is due to hydrogen bonding between the hydroxyl groups and water molecules.
  • Overall Structure: The large, polycyclic structure may hinder solubility, as tightly packed molecules can restrict interactions with solvents.
  • Chemical Modifications: Variations in substituents and the arrangement of cycloalkanes can significantly affect solubility. More hydrophobic regions may lead to decreased solubility in polar environments.
  • Temperature Influence: Increased temperatures could enhance solubility by providing energy that facilitates breaking intermolecular forces within the solid compound.

In summary, while the numerous hydroxyl groups suggest a certain level of favorability for solubility in polar solvents, the complexity and size of the molecule may pose challenges. As noted by chemists, "Molecular complexity often dictates solubility," making this compound an intriguing case study in solubility dynamics.

Interesting facts

Interesting Facts about 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyl-octacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

This intriguing compound, with its complex structure, showcases the vast possibilities of organic chemistry and the nuanced interplay of molecular architecture. Here are some fascinating aspects:

  • Natural Origins: Compounds like these often have natural counterparts, serving significant roles in biological systems, including serving as hormones or signaling molecules.
  • Structural Complexity: Boasting a striking arrangement of rings and functional groups, this octacyclic structure highlights the mastery of modern synthetic techniques that allow chemists to manipulate carbon frameworks.
  • Applications in Medicine: While specific compounds of this class may be investigated for potential pharmaceutical applications, understanding their structure can provide insights into drug design, especially for targeting complex biological pathways.
  • Role in Material Science: The unique properties of such polycyclic compounds can make them candidates for research in material sciences, including polymers and nanomaterials.
  • Synthesis Challenges: The synthesis of such a complex compound can offer a thrilling challenge for chemists, often requiring innovative strategies and multi-step reactions that push the boundaries of synthetic organic chemistry.

As chemists dive deeper into the study of this compound, they may draw connections to various fields including biochemistry, pharmacology, and materials science, reminding us that the beauty of chemistry lies not only in its intricate structures but also in the manifold pathways it opens in our understanding of life and technology.

"Chemistry is the science of connection, revealing the bonds between elements that govern both nature and innovation."

Synonyms
LUTEOSKYRIN
(-)-Luteoskyrin
8,8'-Dihydroxyrugulosin
21884-44-6
NSC160879
Flavomycelin
CHEBI:80711
5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone
RUGULOSIN, 8,8'-DEHYDROXY-
Luteoskyrin, (-)-
NSC-160879
2,2',4,4'5,5',8,8'-Octahydroxy-2,2',3,3'-tetrahydro-7,7'-dimethyl-1,1'-bianthraquinone
5H,6H-6,13a,5a,14-(1,2,3,4)Butanetetraylcycloocta(1,2-b:5,6-b')dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-
Rugulosin,8'-dihydroxy-
LUTEOSKYRIN, (-)
MLS004491708
SCHEMBL846545
octahydroxy(dimethyl)[?]tetrone
CHEMBL2003746
DTXSID0020787
RUGULOSIN,8'-DEHYDROXY-
5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-
NCI60_001196
SMR003288669
NS00026980
Q2110317
Q27149746
Rugulosin,8'-dihydroxy-, (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-
5H,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-