Molecular alignment is key to achieving an ultra-low friction coefficient. We prepared associated carboxylic acids using oleic acid and p-pentylbenzoic acid via hydrogen bonding, involving a benzene ring and an eight-membered cyclic carboxylic acid in the molecules. We investigated frictional properties when these were added into a base oil and found that the associated carboxylic acids decreased the traction coefficient in EHL and boundary lubrication, although the viscosity increased. An in situ micro Fourier transform infrared spectroscope showed that both the eight-membered cyclic carboxylic acid and the benzene ring were oriented parallel to the shearing force, leading to the low friction coefficient.