Glycidols Esters, 2‐Chloropropane‐1,3‐Diols, and 3‐Chloropropane‐1,2‐Diols Contents in Real Olive Oil Samples and their Relation with Diacylglycerols,The Journal of the American Oil Chemists’ Society

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Glycidols Esters, 2‐Chloropropane‐1,3‐Diols, and 3‐Chloropropane‐1,2‐Diols Contents in Real Olive Oil Samples and their Relation with Diacylglycerols
The Journal of the American Oil Chemists’ Society ( IF 1.9 ) Pub Date : 2019-11-06 , DOI: 10.1002/aocs.12302
Angelo Cichelli ₁ , Ylenia Riciputi ₂ , Lorenzo Cerretani ₃ , Maria F. Caboni ₂ , Nicola d'Alessandro ₄

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A series of authentic virgin, refined, and mixtures of olive oils was analyzed for their content of 2‐and 3‐chloropropanediol (MCPD) esters expressed as 2−/3‐MCPD, glycidol (and related glycidyl esters) (GE), and diglycerides (DAG). High concentrations of MCPD and GE were found, above all, in pomace oils, which come from the poorer starting raw materials, while virgin olive oils, as expected, do not contain any process contaminant. On the other hand, DAGs are present in all samples, demonstrating that their involvement in the formation of such contaminants only occurs when temperatures are higher than that used during the refining steps. The lack of correlation between the amounts of MCPD and GE can be ascribed to their completely different chemical stability as the epoxy ring of the GE opens easily, leading to both short‐chain derivatives and/or MCPD itself. This finding can also explain the data about the absence of 2‐MCPD in all the analyzed oil samples: other than the statistical probability and the steric effect of the SN2 formation mechanism, both in favor of the 3‐ derivative, we have also to consider the MCPD formation pathway involving glycidol that, under opportune conditions of refining, can increase the whole amount of 3‐MCPD (under thermodynamic control, 3‐MCPD is more stable).

中文翻译：

实际橄榄油样品中的缩水甘油酯，2-氯丙烷-1,3-二元醇和3-氯丙烷-1,2-二元醇含量及其与二酰基甘油的关系

分析了一系列地道的原始，精制和混合橄榄油的2-和3-氯丙二醇（MCPD）酯的含量，表示为2- / 3-MCPD，缩水甘油（及相关的缩水甘油酯）（GE）和甘油二酸酯（DAG）。首先，在果渣油中发现了高浓度的MCPD和GE，这些果渣油来自较差的起始原料，而按预期，初榨橄榄油不包含任何工艺污染物。另一方面，DAGs存在于所有样品中，这表明它们仅在温度高于精制步骤中使用的温度时才参与这种污染物的形成。MCPD和GE的量之间缺乏相关性，可以归因于它们的化学稳定性完全不同，因为GE的环氧环容易打开，导致短链衍生产品和/或MCPD本身。这一发现还可以解释所有分析过的油样中不存在2-MCPD的数据：除了统计概率和SN2形成机理的空间效应（均有利于3-导数），我们还必须考虑涉及缩水甘油的MCPD形成途径，在适当的提炼条件下可以增加3-MCPD的总量（在热力学控制下，3-MCPD更稳定）。

更新日期：2020-01-06

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