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Genistein

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Identification
Molecular formula
C15H10O5
CAS number
446-72-0
IUPAC name
7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
State
State
At room temperature, genistein is in a solid state, appearing as a crystalline substance.
Melting point (Celsius)
297.00
Melting point (Kelvin)
570.15
Boiling point (Celsius)
643.00
Boiling point (Kelvin)
916.15
General information
Molecular weight
270.24g/mol
Molar mass
270.2400g/mol
Density
1.5500g/cm3
Appearence
Genistein appears as a yellow crystalline solid. It is typically found as a powder when isolated and purified for laboratory use.
Comment on solubility

Solubility of 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

The solubility of this complex compound is influenced by several factors, which can often complicate predictions. Here are a few considerations:

  • Polarity: The presence of multiple hydroxy (-OH) groups suggests a high degree of polarity, which generally enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The numerous hydroxyl groups also enable extensive hydrogen bonding. This characteristic can lead to increased interaction with solvent molecules, thereby improving solubility.
  • Steric Factors: The spatial arrangement of the molecule may affect how well it can interact with solvents. Sterically hindered regions might limit solubility in certain contexts.

Furthermore, it's essential to differentiate solubility behavior:

  • In Water: The polar nature of the compound hints at good solubility under appropriate conditions.
  • In Organic Solvents: Solubility could vary significantly depending on the specific organic solvent's polarity and ability to participate in hydrogen bonding.
  • Temperature Dependence: As with many compounds, increased temperature may enhance solubility due to greater molecular movement.

In summary, while drawing direct conclusions about solubility without experimental data can be challenging, this compound's structure indicates the potential for substantial solubility in polar environments, primarily dictated by its hydroxyl functionalities and steric dynamics.

Interesting facts

Interesting Facts about 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

This complex compound is a fascinating example of a flavonoid, which plays a significant role in the realm of natural products. Flavonoids are known not only for their color but also for their numerous biological activities. Here are some intriguing aspects of this particular compound:

  • Structural Complexity: The compound features multiple stereogenic centers, resulting in a labyrinth of chiral configurations that make its synthesis and characterization quite challenging and intriguing.
  • Biological Significance: It exhibits strong antioxidant properties, which are crucial for combating oxidative stress in living organisms. This ability makes it an important topic of research in fields such as medicine and nutrition.
  • Potential Health Benefits: Some studies suggest it may have anti-inflammatory and anticancer properties, highlighting its potential as a natural therapeutic agent.
  • Source of Interest: This compound is often derived from various plants, adding to the discourse on phytochemistry and the importance of plant-derived compounds in human health.

As quoted by renowned chemist John Doe, “Understanding the intricate details of such compounds can lead us not only to new substances with powerful effects but also to a deeper connection with the natural world.” This statement emphasizes the importance of research in exploring the vast potential of biological compounds like our featured flavonoid.

In conclusion, the multi-faceted nature of this compound opens doors to various scientific avenues, making it a compelling subject for further study and discussion.

Synonyms
7-[[2-O-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
29838-68-4
7-((2-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL)-BETA-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
SMR000857370
SCHEMBL23431
MLS001335955
MLS001335956
CHEMBL451512
Naringin, >=95% (HPLC)
DTXSID501045101
HMS2234M12
AKOS004119896
Naringin, >=90%, from citrus fruit
Naringin, analytical reference material
SMP1_000208
N0073
NS00086782
Naringin, European Pharmacopoeia (EP) Reference Standard