Structure-activity relationships in allergic contact dermatitis induced bymethacrylates - Studies of the influence of side-chain length of methacrylates

Some methacrylates are known to be strong contact sensitizers. To determine the effect of sidechain length on sensitizing potential, we examined 11 de rivatives with linear side chains from C-1 to C-18 in an experimental sensi tization test in guinea pigs. The results showed an increase in the sensiti zing potential with increasing length of the alkyl side chain from C-1 to C -12 The C-12 derivative, lauryl methacrylate, showed the strongest sensitiz ing potential. Further elongation of the alkyl side chain of methacrylates resulted in a decrease in the potential. With respect to the side-chain-len gth-dependent sensitizing potential, the present results correspond well wi th the findings obtained with other compounds like primin, catechols, pheno ls, hydroquinones, and gallates.