Investigation of the salting-in/-out, hydrotropic and surface-active behavior of plant-based hormone and phenolic acid salts

Abstract

HypothesisThe role of hormones and polyphenolic acids in communication and regulation of biological processes can be linked to their physical–chemical interaction with target compounds and water. Further, the variety of polyphenolic acids suggests adjustable hydrotropic properties of these natural compounds. ExperimentsPhase transition temperature (PTT) measurements of binary water/di(propylene glycol) n-propyl ether (DPnP) or propylene glycol n-propyl ether (PnP) systems with sodium dehydroepiandrosterone sulfate (NaDHEAS), indole-3-acetate (NaIAA), indole-3-butyrate (NaIBA) – common hormones -, and sodium polyphenolates should unravel their salting-in/-out properties. Their salting-in/-out behavior was compared to the compounds’ surface-active and structuring properties via surface tension, dynamic light scattering (DLS) and Nuclear magnetic resonance (NMR) experiments. FindingsAll hormone salts were revealed as salting-in agents. PTT, surface tension and DLS measurements indicated surfactant-like behavior of the hormone NaDHEAS, and hydrotropic behavior of NaIAA and NaIBA. The salting-in/-out properties of sodium polyphenolates – in an (anti-)hydrotrope range – are adjustable with functional groups. The (i) absence of nano-structuring in pure water, (ii) the reduction of the DPnP nano-structuring in water in presence of sodium polyphenolates and (iii) the absence of a slope change of the PTT curves at the critical aggregation concentration showed that the DPnP/polyphenolate interactions are of molecular hydrotropic and not of micellar/aggregative nature.