Medium chain triacylglycerols (MCT) have been suggested as efficacious in weight management because they possess greater thermogenic qualities relative to long chain triacylglycerols; however, MCT may also increase circulating lipid concentrations, possibly increasing risk of cardiovascular disease (CVD). The present objective was to examine the effect of a diet supplemented with a functional oil (FctO) composed of energy expenditure-enhancing MCT (50% of fat), cholesterol-lowering phytosterols (22 mg/kg body weight), and triacylglycerol-suppressing n-3 fatty acids (5% of fat), versus a beef tallow-based diet (BT), on plasma lipid and aminothiol concentrations. In a randomized, single-blind, crossover design, partially-inpatient trial, 17 overweight women consumed each oil as part of a controlled, supervised, targeted energy balance diet for 27 days, with 4 or 8 weeks of washout between phases. Mean plasma total cholesterol concentration was lower (P <.0001), by 9.1%, on FctO (4.37 +/- 0.20 mmol/L) versus BT (4.80 +/- 0.20 mmol/L). Mean plasma low-density lipoprotein (LDL) cholesterol was also lower (P <.0001) following FctO (2.39 +/- 0.15 mmol/L) versus BT (2.86 +/- 0.16 mmol/L), representing a 16.0% difference between diets. High-density lipoprotein (HDL) cholesterol and circulating triacylglycerol concentrations remained unaffected by treatment. Ratios of HDL:LDL and HDL:total cholesterol were higher (P <.01) by 22.0% and 11.0%, respectively, on FctO versus BT. Plasma total homocysteine remained unchanged with FctO, but decreased (P <.05) with control, hence higher (P <.05) end points were observed with FctO (6.95 +/- 0.33 micromol/L) versus BT (6.27 +/- 0.28 micromol/L). Plasma glutathione increased (P <.05) by 0.44 micromol/L with FctO supplementation. In conclusion, despite equivocal effects on homocysteine levels, consumption of a functional oil composed of MCT, phytosterols, and n-3 fatty acids for 27 days improves the overall cardiovascular risk profile of overweight women.