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Hypericin

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Identification
Molecular formula
C30H16O8
CAS number
548-04-9
IUPAC name
8-[7,10-dihydroxy-3-methyl-9-[3-methyl-3-(4-methylpent-3-enyl)-7,9,10-trioxo-benzo[f]chromen-8-ylidene]-3-(4-methylpent-3-enyl)benzo[f]chromen-8-ylidene]-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-7,9,10-trione
State
State

At room temperature, hypericin exists as a solid with a crystalline structure. It is often derived from natural sources and can exhibit a dense, stable form.

Melting point (Celsius)
320.00
Melting point (Kelvin)
593.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
504.44g/mol
Molar mass
504.4440g/mol
Density
1.6500g/cm3
Appearence

Hypericin is a naphthodianthrone, a kind of polycyclic aromatic compound that appears as a dark red crystalline solid. It is a naturally occurring pigment found mainly in the St. John's Wort plant, giving it a distinctive red or purplish color. This compound can have a striking appearance when dissolved, forming brightly colored solutions.

Comment on solubility

Solubility of 8-[7,10-dihydroxy-3-methyl-9-[3-methyl-3-(4-methylpent-3-enyl)-7,9,10-trioxo-benzo[f]chromen-8-ylidene]-3-(4-methylpent-3-enyl)benzo[f]chromen-8-ylidene]-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-7,9,10-trione (C30H16O8)

The solubility of this complex organic compound is largely influenced by its intricate structure, comprising hydrophilic and hydrophobic parts. As a result, understanding its solubility can be multifaceted:

  • Hydrophobic Character: The presence of multiple alkyl chains, such as the 4-methylpent-3-enyl groups, can lead to significant hydrophobic interactions, which may result in low solubility in polar solvents like water.
  • Hydrophilic Groups: The hydroxy (−OH) functional groups might enhance solubility in aqueous environments to some degree, promoting interactions with water molecules.
  • Solvent Dependency: It may show variable solubility behavior depending on the solvent system employed. For instance, it is likely to dissolve better in organic solvents such as ethanol, acetone, or dimethyl sulfoxide (DMSO).
  • Concentration Effects: At higher concentrations, precipitation might occur, signifying a limit to its solubility in a given solvent.

In general, while the compound may exhibit some solubility in specific solvents due to its hydrophilic functionalities, its overall tendency is to be less soluble in polar solvents due to its substantial hydrophobic characteristics. As noted, "solubility is a key factor affecting the bioavailability and efficacy of compounds" in various applications.

Interesting facts

Interesting Facts about 8-[7,10-Dihydroxy-3-methyl-9-[3-methyl-3-(4-methylpent-3-enyl)-7,9,10-trioxo-benzo[f]chromen-8-ylidene]-3-(4-methylpent-3-enyl)benzo[f]chromen-8-ylidene]-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-7,9,10-trione

This compound, with its complex structure and intricate name, belongs to a class of molecules known for their fascinating properties and potential applications in various fields.

1. Biological Significance

Many compounds similar to this one, particularly those derived from natural sources, exhibit significant biological activities:

  • Antioxidant Properties: Polyphenolic compounds, like this one, may have antioxidative qualities that help in combating oxidative stress.
  • Anti-inflammatory Effects: Certain components in similar categories are studied for their anti-inflammatory actions, making them potential candidates for therapeutic use.

2. Chemical Complexity

The intricate structure of this compound showcases the beauty of organic chemistry:

  • Multiple Functional Groups: The presence of various hydroxyl groups and keto functionalities indicates high reactivity and opens avenues for further functionalization.
  • Chromene Framework: Compounds containing chromene structures are often investigated for their diverse chemical properties and biological activities.

3. Synthesis and Applications

The synthesis of such complex organic molecules is a thrilling venture:

  • Challenges in Synthesis: The multi-step synthesis often requires careful planning and execution, utilizing techniques like refluxing, reduction, or oxidation.
  • Potential Uses: Given its structural characteristics, this compound could serve as a lead compound in drug development or as an advanced pigment in the materials science sector.

In summary, the exploration of this compound not only highlights the complexity inherent in organic synthesis but also opens doors to potential medicinal advances and materials innovation. The ongoing research in this area continues to intrigue chemists seeking to unlock the secrets behind such multifaceted molecules.