Technical Abstract: Five branched oleochemicals were prepared from commercially available methyl oleate and common organic acids and their lubricant properties were determined. These branched oleochemicals are characterized as alpha-hydroxy ester derivatives of methyl oleate. These derivatives show improved low temperature properties over olefinic oleochemicals by pour point and cloud point measurements. The derivatization also increased thermo-oxidative stability, measured using both Pressurized Differential Scanning Calorimetry (PDSC) and Thin Film Micro Oxidation (TFMO). Tribological behaviors were evaluated as additives in soybean oil and polyalphaolefin using four-ball and ball-on-disk configurations. These derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all test loads. Their surface tensions were determined and a trend of larger branches causing lower surface tension was also observed, except in the case where the carbonyl containing levulinic acid was used. It had a higher surface tension. Overall, the data indicate that some of these derivatives have significant potential to be used as a lubricating oil or fuel additive.