Document Detail


Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD.
MedLine Citation:
PMID:  18348037     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
W Seefelder; N Varga; A Studer; G Williamson; F P Scanlan; R H Stadler
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Publication Detail:
Type:  Journal Article    
Journal Detail:
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:
Created Date:  2008-03-18     Completed Date:  2008-11-10     Revised Date:  2009-08-13    
Medline Journal Info:
Nlm Unique ID:  101485040     Medline TA:  Food Addit Contam Part A Chem Anal Control Expo Risk Assess     Country:  England    
Other Details:
Languages:  eng     Pagination:  391-400     Citation Subset:  IM    
Affiliation:
Quality and Safety Assurance Department, Nestlé Research Center, Nestec Ltd, CH-1000 Lausanne 26, Switzerland. walburga.seefelder@rdls.nestle.com
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MeSH Terms
Descriptor/Qualifier:
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:
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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