| Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD. | |
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MedLine Citation:
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PMID: 18348037 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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3-Mono-chloropropane-1,2-diol (3-MCPD) is a contaminant that occurs in food in its free (diol) form as well as in an esterified (with fatty acids) form. Using a simple intestinal model, it was demonstrated that 3-MCPD monoesters and 3-MCPD diesters are accepted by intestinal lipase as substrates in vitro. Under the chosen conditions, the yield of 3-MCPD from a 3-MCPD monoester was greater than 95% in approximately 1 min. Release from the diesters was slower, reaching about 45, 65 and 95% of 3-MCPD after 1, 5 and 90 min of incubation, respectively. However, in human, the hydrolysis of 3-MCPD esters is unlikely to release 100% as 3-MCPD, as triglycerides and phospholipids are hydrolysed in the intestine liberating 2-monoglycerides. Assuming a similar metabolism for 3-MCPD esters as that known for acylglycerols in humans in vivo, the de-esterification in positions 1 and 3 would thus be favoured by pancreatic lipases. Therefore, 3-MCPD, and 3-MCPD-2 monoesters would be released, respectively, from the 1-/3-monoesters, and the diesters potentially present in food. Hence, information on the exact amounts of the partial fatty acid chloroesters, i.e. 3-MCPD mono- and diesters, is important to assess the contribution of foods to the bioavailability of 3-MCPD. Therefore, a rapid method for the determination of the ratio of 3-MCPD monoesters to diesters in fats and oils was developed using gas chromatography-mass spectrometry (GC-MS) and isotopically labelled 3-MCPD esters as internal standards. The analysis of 11 different samples of fat mixes typically employed in food manufacturing demonstrated that a maximum of about 15% of the total amount of 3-MCPD bound in esters is present in the monoesterified form. The potentially slower release of 3-MCPD from 3-MCPD diesters, and the mono- to diesters ratio suggest that 3-MCPD esters may in fact contribute only marginally to the overall dietary exposure to 3-MCPD. Further work on the bioavailability, metabolism and possible toxicity of chloroesters per se is warranted. |
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Authors:
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W Seefelder; N Varga; A Studer; G Williamson; F P Scanlan; R H Stadler |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment Volume: 25 ISSN: 1944-0057 ISO Abbreviation: Food Addit Contam Part A Chem Anal Control Expo Risk Assess Publication Date: 2008 Apr |
Date Detail:
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Created Date: 2008-03-18 Completed Date: 2008-11-10 Revised Date: 2009-08-13 |
Medline Journal Info:
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Nlm Unique ID: 101485040 Medline TA: Food Addit Contam Part A Chem Anal Control Expo Risk Assess Country: England |
Other Details:
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Languages: eng Pagination: 391-400 Citation Subset: IM |
Affiliation:
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Quality and Safety Assurance Department, Nestlé Research Center, Nestec Ltd, CH-1000 Lausanne 26, Switzerland. walburga.seefelder@rdls.nestle.com |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Bile / chemistry Bile Acids and Salts / metabolism Biological Availability Esters / metabolism Fatty Acids / metabolism Food Analysis / methods* Food Contamination / analysis* Gas Chromatography-Mass Spectrometry Humans Hydrolysis Lipase / antagonists & inhibitors, metabolism Lipolysis Magnetic Resonance Spectroscopy Pancreatin / metabolism Plant Oils / chemistry* Reproducibility of Results Substrate Specificity Swine alpha-Chlorohydrin / analysis, chemistry, metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Bile Acids and Salts; 0/Esters; 0/Fatty Acids; 0/Plant Oils; 8049-47-6/Pancreatin; 96-24-2/alpha-Chlorohydrin; EC 3.1.1.3/Lipase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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