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Phloretin

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Identification
Molecular formula
C21H24O10
CAS number
60-82-2
IUPAC name
7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(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, phloretin is typically found in a solid state. Its crystalline solid form allows it to be easily handled and stored at typical laboratory conditions.

Melting point (Celsius)
261.60
Melting point (Kelvin)
534.80
Boiling point (Celsius)
825.82
Boiling point (Kelvin)
1 098.97
General information
Molecular weight
436.41g/mol
Molar mass
436.4000g/mol
Density
1.4980g/cm3
Appearence

Phloretin typically appears as a white crystalline solid. It is often available in powder form and is known for its slightly sweet taste. It can exhibit a degree of yellowish tint depending on its purity and exposure to environmental factors such as light and air.

Comment on solubility

Solubility Characteristics

The compound 7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one, with the chemical formula C21H24O10, exhibits interesting solubility behaviors that can be attributed to its complex structure. Here are some key points regarding its solubility:

  • Polar Nature: The presence of multiple hydroxyl (-OH) groups in the molecule suggests that it is likely to be polar, which generally correlates with increased solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups can engage in hydrogen bonding, enhancing the solubility in aqueous solutions significantly.
  • Solvent Compatibility: It may also have moderate solubility in organic solvents that have polar characteristics, but less so in non-polar solvents.
  • Application in Solutions: Its solubility profile makes it suitable for applications in formulations where solubility is critical, such as in pharmaceutical and cosmetic products.

In conclusion, while the intricate arrangement of functional groups can complicate its overall solubility characteristics, the polar nature and ability to form hydrogen bonds are significant factors to consider when evaluating the solubility of this compound.

Interesting facts

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

This fascinating compound, which belongs to the class of flavonoids, showcases a plethora of intriguing features that pique the interest of chemists and researchers alike. Here are some notable facts:

  • Flavonoid Structure: The compound is a complex structure characterized by its multiple hydroxyl groups, contributing to its solubility and biological activity.
  • Antioxidant Properties: Like many flavonoids, it exhibits significant antioxidant capabilities, which means it can help neutralize harmful free radicals in the body.
  • Potential Health Benefits: Research suggests that flavonoids may have a role in promoting health by reducing the risk of chronic diseases, such as heart disease and certain cancers. This compound may be studied for its effects on cardiovascular health and inflammation.
  • Cyclic Compounds: The presence of tetrahydropyran rings contributes to the compound’s unique three-dimensional shape, which can play a critical role in its interaction with biological molecules.
  • Biological Source: Natural flavonoids, often found in fruits, vegetables, and herbal plants, are of great interest not only due to their health-promoting properties but also for their roles in plant pigmentation and UV protection.
  • Research Focus: Current research is increasingly focusing on understanding the specific mechanisms through which this compound exerts its effects at the molecular level, information that could lead to the development of new pharmacological agents.

As the demand for natural products in medicine and dietary supplements increases, compounds such as this one continue to be at the forefront of chemical and biological research, bridging the gap between chemistry and health sciences.

Synonyms
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)-, (2S)-
Naringenin 7-Rhamnoglucoside
4',5,7-trihydroxyflavanone 7-rhamnoglucoside
4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2R)-
7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
NSC93745
58001-41-5
MFCD00148888
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)-, (2S)-
7-(4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Naringenin 7-neohesperidoside
SCHEMBL13237107
SCHEMBL20386955
DTXSID10860071
DFPMSGMNTNDNHN-UHFFFAOYSA-N
HMS3369C10
HMS3374A04
HMS3651C20
(R)-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
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)-, (2S)-
BCP28297
7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
SY069758
Naringoside;Aurantiin; AI3-19008; AI319008; AI3 19008
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside