Why delphinidin-3,5-diglucoside is almost insoluble in water while delphinidin-3-glucoside dissolves easily in water?
Generally, glycosylatio is assumed to improve hydrophilicity of anthocyanin.
What mechanism caused this phenomenon?
The difference in solubility between delphinidin-3,5-diglucoside and delphinidin-3-glucoside in water can be attributed to their respective chemical structures. Delphinidin-3,5-diglucoside contains two glucose molecules attached to the delphinidin core, whereas delphinidin-3-glucoside has only one glucose moiety. The additional glucose molecule in delphinidin-3,5-diglucoside introduces steric hindrance, making it more difficult for the compound to interact with water molecules through hydrogen bonding. As a result, delphinidin-3,5-diglucoside exhibits limited solubility in water. On the other hand, delphinidin-3-glucoside, with its single glucose unit, has a more accessible hydroxyl group on the delphinidin structure, allowing for stronger interactions with water molecules and thus higher solubility.
Why delphinidin-3,5-diglucoside is almost insoluble in water while delphinidin-3-glucoside dissolves easily in water? (1) delphinidin-3,5-diglucoside is Bioside but delphinidin-3-glucoside is Monooside (2) The number of hydroxyl groups in the molecule; (3) The nature, number, and the position of glycosylation; (4) The nature and number of aromatic or aliphatic acids attached to the glucosyl residue.
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