Preparation of a Regioselective Quercetin-3-palmitate and Its Using for Boosting Cooking Oil Stability.

Abstract

Due to over worldwide use of frying oil, and due to its oxidation and deterioration after the usage for short time, huge oil amounts are wasted. So, most attempts are aimed to increase oil stability. Quercetin is a common name for the lipophobic strong natural phenolic antioxidant 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one. Thus, its solubility had been improved by converting it to a lipophilic compound via its appending to a fatty acid residue. So, regioselectively 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[Hexadecanyl]oxychromen-4-one commonly named as (Quercetin-3-palmitate) was synthesized. The formed compound was confirmed based on its elemental analysis and spectral data (IR, 1H NMR and MS). The partition coefficient of Quercetin-3-palmitate in octanol/ water (k) was determined and compared to that of palmitic acid and quercetin individually to prove its solubility enhancement. Its radical scavenging activity was then tested. The effect of this new antioxidant compound on the oil stability was studied through the frying process. All physical and chemical parameters of this oil were considered before and after the frying process compared to another reference antioxidant (TBHQ) and control sample. The safety of this compound was determined by acute oral toxicity using albino mice. The liver and kidney functions of these mice were also examined. The results showed non-significant change. A sensory evaluation of the fried potato chips has been done. The results showed that the properties of the potato chips were improved by adding Quercetin-3-palmitate to the oil. Thus, good protection against frying oils oxidation was achieved via the addition of Quercetin-3-palmitate. The Quercetin-3-palmitate effectiveness is mainly attributed to its stability at high temperatures. Moreover, Quercetin-3-palmitate was found to be a safe compound according to an acute lethal toxicity test. Consequently, it can be used as a food additive.