An investigation was reported concerning the chiral analysis of some Imino-4-Hesperetin and the impact of different factors on their chiral high-performance liquid chromatographic separation. Using Schiff bases reactions, new Imino-4-Hesperetin derivatives had been elaborated by the reaction of Hesperetin with various diamines differ only in their carbon chain length which ranged between 4, 8 and 10 carbons; Yields were very acceptable and ranged between 77 and 89%. A chiral separation was then employed by a conventional HPLC with six different polysaccharide-based chiral stationary phases. The resolution, capacity and separation factors obtained were good (2.11 ≤ Rs ≤ 4.5); (1.25 ≤ k′ ≤ 8.71) and (1.16 ≤ α ≤2.57). Flow rate was about 0.3–0.5 mL/min. The factors affected the chiral resolution including the role of the carbon chain length which did have an impact on the resolution of these derivatives were discussed.
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