Fatty acid esters of 3-chloropropane-1,2-diol in edible oils. 2006

Z Zelinková, and B Svejkovská, and J Velísek, and M Dolezal
Department of Food Chemistry and Analysis, Institute of Chemical Technology Prague, Technická 1905, 166 28 Prague, Czech Republic.

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 microg kg-1 (LOD) to 24 microg kg-1. Surprisingly, bound 3-MCPD levels were much higher and varied between <100 (LOD) and 2462 microg kg-1. On average, virgin oils had relatively low levels of bound 3-MCPD, ranging from <100 (LOD) to <300 microg kg-1 (LOQ). Higher levels of bound 3-MCPD were found in oils from roasted oilseeds (337 microg kg-1) and in the majority of refined oils (<300-2462 microg kg-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 microg kg-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 microg kg-1).

UI MeSH Term Description Entries
D008401 Gas Chromatography-Mass Spectrometry A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds. Chromatography, Gas-Liquid-Mass Spectrometry,Chromatography, Gas-Mass Spectrometry,GCMS,Spectrometry, Mass-Gas Chromatography,Spectrum Analysis, Mass-Gas Chromatography,Gas-Liquid Chromatography-Mass Spectrometry,Mass Spectrometry-Gas Chromatography,Chromatography, Gas Liquid Mass Spectrometry,Chromatography, Gas Mass Spectrometry,Chromatography, Mass Spectrometry-Gas,Chromatography-Mass Spectrometry, Gas,Chromatography-Mass Spectrometry, Gas-Liquid,Gas Chromatography Mass Spectrometry,Gas Liquid Chromatography Mass Spectrometry,Mass Spectrometry Gas Chromatography,Spectrometries, Mass-Gas Chromatography,Spectrometry, Gas Chromatography-Mass,Spectrometry, Gas-Liquid Chromatography-Mass,Spectrometry, Mass Gas Chromatography,Spectrometry-Gas Chromatography, Mass,Spectrum Analysis, Mass Gas Chromatography
D010938 Plant Oils Oils derived from plants or plant products. Oils, Plant,Oils, Vegetable,Plant Oil,Vegetable Oil,Vegetable Oils,Oil, Plant,Oil, Vegetable
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D005227 Fatty Acids Organic, monobasic acids derived from hydrocarbons by the equivalent of oxidation of a methyl group to an alcohol, aldehyde, and then acid. Fatty acids are saturated and unsaturated (FATTY ACIDS, UNSATURATED). (Grant & Hackh's Chemical Dictionary, 5th ed) Aliphatic Acid,Esterified Fatty Acid,Fatty Acid,Fatty Acids, Esterified,Fatty Acids, Saturated,Saturated Fatty Acid,Aliphatic Acids,Acid, Aliphatic,Acid, Esterified Fatty,Acid, Saturated Fatty,Esterified Fatty Acids,Fatty Acid, Esterified,Fatty Acid, Saturated,Saturated Fatty Acids
D005504 Food Analysis Measurement and evaluation of the components of substances to be taken as FOOD. Analysis, Food,Analyses, Food,Food Analyses
D005506 Food Contamination The presence in food of harmful, unpalatable, or otherwise objectionable foreign substances, e.g. chemicals, microorganisms or diluents, before, during, or after processing or storage. Food Adulteration,Adulteration, Food,Adulterations, Food,Contamination, Food,Contaminations, Food,Food Adulterations,Food Contaminations
D005511 Food Handling Any aspect of the operations in the preparation, processing, transport, storage, packaging, wrapping, exposure for sale, service, or delivery of food. Food Processing,Handling, Food,Processing, Food
D005990 Glycerol A trihydroxy sugar alcohol that is an intermediate in carbohydrate and lipid metabolism. It is used as a solvent, emollient, pharmaceutical agent, or sweetening agent. 1,2,3-Propanetriol,Glycerin,1,2,3-Trihydroxypropane,Glycerine
D006358 Hot Temperature Presence of warmth or heat or a temperature notably higher than an accustomed norm. Heat,Hot Temperatures,Temperature, Hot,Temperatures, Hot
D000517 alpha-Chlorohydrin A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents. alpha-Chlorhydrin,3-Chloro-1,2-propanediol,3-Chloropropanediol,3-MCPD,3-Monochloropropane-1,2-diol,Glycerol alpha-Monochlorohydrin,U-5897,3 Chloro 1,2 propanediol,3 Chloropropanediol,3 Monochloropropane 1,2 diol,Glycerol alpha Monochlorohydrin,U 5897,U5897,alpha Chlorhydrin,alpha Chlorohydrin,alpha-Monochlorohydrin, Glycerol

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