Thermal conversion kinetics and solubility of soy isoflavones in subcritical water extraction

The conversion of isoflavones during subcritical water extraction were studied using first-order reaction kinetics modeling. Isoflavones were extracted from soybean using temperatures from 100℃ to 180℃ for 3 to 30 min. It was found that malonylgenistin was the most thermally unstable, with little being detected above 100℃. The optimal extraction temperatures for acetylgenistin (AG), genistin (G), and genistein (GE) were 120℃, 150℃, and 180℃, respectively. A larger sum of the numbers of both hydroxyl groups and oxygen molecules was associated with a lower melting point and optimal extraction temperature. Kinetics modeling of reaction rate constant k and activation energy E_a showed that all of the reaction rates tended to increase with temperature, with the relationship fitted well by a first-order model in nonlinear regression. For temperatures between 100℃ and 150℃, AG → G and AG → GE conversions showed the highest rate constants, but G → GE and G → D₃ (degraded G) conversions became dominant at 180℃. Chemical compounds studied in this article: genistein (PubChem CID: 5280961), genistin (PubChem CID: 5281377), 6″-O-malonylgenistin (PubChem CID: 15934091), 6″-O-acetylgenistin (PubChem CID: 5315831).