Fatty acid esters of 3-chloropropane-1,2-diol in edible oils

A series of 25 virgin and refined edible oils, obtained from retailers, was analyzed for levels of free 3-chloropropane-1,2-diol (3-MCPD) and 3-MCPD released from esters with higher fatty acids (bound 3-MCPD). Oils containing free 3-MCPD ranging from < 3 mu gkg(-1) (LOD) to 24 mgkg(-1). Surprisingly, bound 3-MCPD levels were much higher and varied between < 100 (LOD) and 2462 mu gkg(-1). On average, virgin oils had relatively low levels of bound 3-MCPD, ranging from < 100 (LOD) to < 300 mu gkg(-1) (LOQ). Higher levels of bound 3-MCPD were found in oils from roasted oilseeds (337 mu gkg(-1)) and in the majority of refined oils (< 300-2462 mu gkg(-1)), including refined olive oils. In general, it appears that the formation of bound 3-MCPD in oils is linked to preliminary heat treatment of oilseeds and to the process of oil refining. Analysis of unrefined, de-gummed, bleached, and deodorized rapeseed oil showed that the level of bound MCPD decreased during the refining process. However, additional heating of seed oils for 30 min at temperatures ranging from 100 to 280 degrees C, and heating at 230 degrees C (260 degrees C) for up to 8 h, led to an increase in bound 3-MCPD levels. On the other hand, heating of olive oil resulted in a decrease in bound 3-MCPD levels. For comparison, fat isolated from salami was analyzed for intact fatty acid esters of 3-MCPD. This fat contained bound 3-MCPD at a level of 1670 mu gkg(-1) and the fatty acid esters of 3-MCPD mainly consisted of 3-MCPD diesters; monoesters of 3-MCPD were present in smaller amounts. The major types of 3-MCPD diesters (about 85%) were mixed diesters of palmitic acid with C18 fatty acids (stearic, oleic, linoleic acids). These diesters were followed by 3-MCPD distearate (11%) and 3-MCPD dipalmitate (4%). Generally, very little 3-MCPD existed as the free compound (31 mu gkg(-1)).