Why Naringin solubility in water is low but solubility of this compound in aprotic solvent like THF and DMF is high? I wanna the reason of this phenomena from organic perspective.
Best regards
Mohammad
Dear Mohamad,
Hydrophilicity of flavones increases with the number of free hydroxyl groups. Naringin, a flavonone glycoside, has only two free hydroxyl groups; the heterocyclic ring (the middle ring) does not possess a free hydroxyl group, which is found in quercetin, a flavonol with 5 free hydroxyl groups. The B-ring of naringin has a single free hydroxyl group. With its limited number of free hydroxyl groups, naringin possessing two phenolic (aromatic) rings, may partition better in lipid solvents (example, methanol). Flavonones possess low solubility in polar solvents. Generally, flavonoid glucosides are more soluble in water than their aglycones (free non-sugar derivatives).
The increase in solubility of the citrus flavonone, naringin, with the increase in temperature was not pronounced up to 45 degrees.
https://archive.org/stream/solubilityofnari78pull#page/n1/mode/2up
The solubility of naringin in water at 37 °C it was found to be only 1.9 μg per mL. Complexation of naringin with the cyclic oligosaccharide, beta-cyclodextrin, greatly increased its solubility in water.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3509578
Regards!
You may find useful information regarding the relationship of temperature to degree of solubility. Please refer to Solubility of naringin in ethanol and water mixtures from 283.15 to 318.15 K at https://www.researchgate.net/publication/270398145_Solubility_of_naringin_in_ethanol_and_water_mixtures_from_283.15_to_318.15_K
Article Solubility of naringin in ethanol and water mixtures from 28...
naringin contain number of OH may inhibit or prohibit configuration, also all flavonoids contain rings
Hi dear El-Hadidy
Its possible explain more or explain with understandable example.
Best Regards
Dear Mohamad,
Hydrophilicity of flavones increases with the number of free hydroxyl groups. Naringin, a flavonone glycoside, has only two free hydroxyl groups; the heterocyclic ring (the middle ring) does not possess a free hydroxyl group, which is found in quercetin, a flavonol with 5 free hydroxyl groups. The B-ring of naringin has a single free hydroxyl group. With its limited number of free hydroxyl groups, naringin possessing two phenolic (aromatic) rings, may partition better in lipid solvents (example, methanol). Flavonones possess low solubility in polar solvents. Generally, flavonoid glucosides are more soluble in water than their aglycones (free non-sugar derivatives).
The increase in solubility of the citrus flavonone, naringin, with the increase in temperature was not pronounced up to 45 degrees.
https://archive.org/stream/solubilityofnari78pull#page/n1/mode/2up
The solubility of naringin in water at 37 °C it was found to be only 1.9 μg per mL. Complexation of naringin with the cyclic oligosaccharide, beta-cyclodextrin, greatly increased its solubility in water.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3509578
Regards!
Dr. El-Hadidy has mentioned hydroxyl groups (-OH). The number of free OH (phenolic) groups in a flavone moiety influences the water solubility of the molecule.
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