(<i>E</i>)-2-Heptenal in Soymilk: A Nonenzymatic Formation Route and the Impact on the Flavor Profile
Xiaoxiao Feng, Yufei Hua, Xingfei Li, Caimeng Zhang, Xiangzhen Kong, Yeming Chen
Abstract
Flavor is an essential quality characteristic of soymilk. (E)-2-Heptenal has a fatty and fruity flavor with the sensory threshold value of 13 μg/L in water. This study demonstrated that the formation of (E)-2-heptenal was independent of the lipoxygenase (LOX) and hydroperoxide lyase (HPL) activity as well as oxygen concentration but was related to the presence/absence of Fe2+ and chelators. In a dry matter base, soybean hypocotyls generated a much higher amount of (E)-2-heptenal than cotyledons. A phospholipid hydroperoxide was purified from the chloroform/methanol extract of soybean hypocotyls and was identified as 1-palmitoyl-2-(12-hydroperoxyoctadecadienoyl)-sn-glycerol-3-phosphatidylethanol-amine (12-PEOOH). The decomposition of 12-PEOOH in the presence of ferrous ions to form (E)-2-heptenal was studied in a model system. The rate of decomposition decreased sharply at pH values higher than 6, but the molar conversion of 12-PEOOH to (E)-2-heptenal increased with an increase of pH. At a constant pH of 5.8, the decomposition rate of 12-PEOOH was positively linearly related to the Fe2+ concentration, while the molar conversion to (E)-2-heptenal was 74% and independent of the Fe2+ concentration. The formation of radicals LOO• and R• showed similar pH and Fe2+ concentration dependence with those of (E)-2-heptenal. (E)-2-Heptenal displayed an enhancement of bean aroma and fruity flavor of soymilk at low concentrations, but a fatty flavor was noticed at high concentrations.