To obtain information about the influence of hydrogen bonding on the monolayer behavior and molecular packing, amphiphiles with two hydroxyl groups attached to different positions in the alkyl chain are investigated at the air-water interface using K-A-isotherms, constant surface pressure relaxation measurements and Brewster angle microscopy (BAM). Monolayers of different racemic and enantiomeric methyl dihydroxyoctadecanoates show evidence that the position of the two hydroxyl groups and the conformation of the molecules influence the formation and the stability of the monolayers and lead to enantiomorphous structures. The two enantiomers of methyl erythro-9,10- dihydroxyoctadecanoate form feather-like structures which are curved clockwise or counterclockwise as observed by Brewster angle microscopy.