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Xanthohumol

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Identification
Molecular formula
C21H22O5
CAS number
6754-58-1
IUPAC name
[2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone
State
State

At room temperature, xanthohumol is typically in a solid state. It is stable when stored properly, avoiding exposure to air and light.

Melting point (Celsius)
170.00
Melting point (Kelvin)
443.15
Boiling point (Celsius)
450.00
Boiling point (Kelvin)
723.15
General information
Molecular weight
354.41g/mol
Molar mass
354.4140g/mol
Density
1.2345g/cm3
Appearence

Xanthohumol is a yellow-brown crystalline solid. It may appear as a powder and has a characteristic phenolic odor. It is known for its stability when stored under appropriate conditions.

Comment on solubility

Solubility of [2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone

The solubility of the compound C21H22O5 can be characterized by several factors that influence how it interacts with solvents. Its complex structure, which features multiple functional groups, plays a significant role in its solubility properties.

Factors Affecting Solubility

  • Polarity: The presence of hydroxyl (-OH) groups suggests that this compound may exhibit some degree of polarity, potentially enhancing solubility in polar solvents such as water.
  • Hydrophobic Regions: The alkene side chains (3-methylbut-2-enyl) contribute a hydrophobic character, which could limit its solubility in highly polar solvents.
  • Hydrogen Bonding: The ability of the -OH groups to form hydrogen bonds can lead to increased solubility in alcohols or other hydrogen bond donors.
  • Temperature: As with many organic compounds, solubility may increase with temperature, depending on the solvent used.

In summary, while it is plausible that this compound may exhibit some solubility in polar organic solvents like ethanol or methanol due to its hydrophilic hydroxyl groups, its overall solubility may be reduced in pure water due to the presence of hydrophobic regions. Further studies would be beneficial to quantify its solubility in various solvents.

Interesting facts

Interesting Facts about [2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone

This compound is a fascinating member of the family of phenolic compounds, which are renowned for their diverse biological activities and potential applications in various fields. Here are some interesting aspects of this specific compound:

  • Structural Complexity: The compound features multiple functional groups, including hydroxyl groups and methoxy substituents, attached to a phenyl ring, which enhances its chemical reactivity and interaction with biological systems.
  • Antioxidant Properties: Many phenolic compounds exhibit significant antioxidant activity, which is essential for combating oxidative stress in living organisms. This characteristic may contribute to health benefits when this compound is studied for potential medicinal use.
  • Natural Sources: Compounds with similar structures can often be found in various plant species, highlighting their role in plant defense mechanisms and their potential as nutraceuticals.
  • Biological Research: The complex arrangement of substituents on the phenolic core suggests a promising avenue for further research, potentially unveiling novel therapeutic agents.
  • Applications in Material Science: Due to its phenolic nature, derivatives of this compound could be explored in the development of polymers and coatings, owing to their stability and resistance properties.

As a student or researcher, delving into the characteristics of this compound could open up new pathways in both chemistry and interdisciplinary studies, bridging gaps between organic chemistry, pharmacology, and materials science.

In the words of a prominent chemist, “The beauty of chemistry lies in the intricate dance of molecules, ever-changing yet profoundly impactful.” Exploring compounds like this gives us critical insights into that dance.

Synonyms
Vismiaphenone D
[2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone
(2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl)-(4-hydroxyphenyl)methanone
CHEMBL463208
SCHEMBL4003423
NSC709862
NSC-709862
219744-90-8