Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths.

The skin penetrative action of high purity cis-omega-12-octadecenoic acid (petroselinic acid, HP-PSA) on rat skin was compared with that of high purity cis-omega-9-octadecenoic acid (oleic acid, HP-OA), following treatment of rat intact skin surface with either 0.05 M HP-PSA or HP-OA in propylene glycol (PG), using Fourier transform/attenuated total reflection (FT-IR/ATR) analysis. Both HP-PSA and HP-OA disordered the lipid structures of the stratum corneum region to a similar extent. Removal of the extractable lipids of the stratum corneum region was marked with HP-PSA/PG but was very slight upon HP-OA/PG treatment. The spectra of the amide II region which originated from proteins suggests that HP-PSA/PG more rapidly disordered the protein structures of both the stratum corneum and the dermis than HP-OA/PG. However, the extent of disordering of the protein structures was presumed to be similar between these two skin penetration enhancers at the maximum level. Enhancement of PG flux in the dermis showed strong positive correlation with the degree of dermis-disordering action of HP-PSA/PG and HP-OA/PG. These results demonstrate that HP-PSA, which has a double bond at an even numbered position (omega-12), more rapidly affects the perturbation of the structures of both the stratum corneum and the dermis than HP-OA, which has the double bond at an odd numbered position (omega-9). Differences in the physicochemical properties of HP-PSA and HP-OA which originate from differences in the double bond position most likely determine the efficacy of these compounds as skin penetration enhancers.