In this article we present a study of a new class of surfactants denoted as PEG1500-12-acyloxystearates, which have potential use as pharmaceutical solubilizers. These amphiphilic molecules present interesting properties with regard to cell damage effects. PEG1500-12-acyloxystearates with C(14) to C(16) acyloxy chains cause little or no damage to red blood and intestinal cells, whereas the surfactants with shorter chains, from C(8) to C(12), induce measurable damage. To start unraveling the reason why there is this rather marked dependence of the cell damage effect on surfactant chain length, we have carried out systematic studies of adsorption properties of the surfactants onto phospholipid bilayers by means of ellipsometry. The rate of incorporation of the surfactants in the lipid membrane decreases with increasing length of the acyloxy chain. Cryo-TEM images strengthen the ellipsometry results by showing that the dissolution of the phospholipid bilayer is slower for the surfactants of the series having longer chains.