3-單氯丙二醇酯（3-monochloro-1,2-propanediol esters, 3-MCPDEs）及2-單氯丙二醇酯（2-monochloro-1,3-propanediol esters, 2-MCPDEs）為食品及食品原料在高溫（≥200°C）製程中產生之污染物，主要經由植物油精製程序之高溫脫臭步驟產生，常隱身於日常接觸到之複合食品、加工食品及嬰幼兒食品。3-及2-MCPDEs經攝取後，於胃腸道消化時會轉變為游離型3-及2-MCPD，為主要之毒性來源。3-MCPD具有腎臟及生殖毒性，亦已被國際癌症研究署（IARC）歸類為人類可能致癌物（Group 2B），且歐洲食品安全局（EFSA）於2018年訂定其每日容許攝入量（TDI）為2 μg/kg bw/day；2-MCPD之毒性資料有限，實驗動物在高劑量下，於橫紋肌、心臟、腎臟和肝臟中觀察到嚴重之毒性作用。當今，食品中3-及2-MCPDEs量測普遍使用氣相層析質譜儀（GC/MS）之間接分析法，過程中常因水解衍生化步驟之不穩定性增加分析結果之不確定性，且無法取得個別同源物之分布資訊，使得後續暴露評估及溯源探討有所限制。此外，近年來國人外食比例增長，多數研究僅針對少部分高風險食品進行3-MCPDEs含量調查，忽視2-MCPDEs之潛在風險，有其必要開發適用於同時分析各種加工食品中3-及2-MCPDEs之方法，俾利日後完善我國3-及2-MCPDEs背景值含量資料庫及國人膳食攝入風險評估。因此，本研究目的為開發適用於廣泛食品基質之高解析液相層析儀-電灑式離子化-串聯式質譜儀（HPLC-EIS-MS/MS）之直接分析方法，並以部分國內市售加工食品檢驗所含24種3-及2-MCPDEs之污染情形，驗證所開發之直接分析方法之可用性。本研究依照食品複雜程度將基質區分為三大類（油脂類、低脂食品類及高脂食品類）開發有效之前處理方法，再使用HPLC-EIS-MS/MS之最佳化層析梯度及質譜條件進行定量及定性分析，經品保品管規範驗證後，已可偵測加工食品中18種3-MCPDEs及6種2-MCPDEs之污染含量。前處理測試結果顯示，油脂類以溶解性高之20%乙酸乙酯/甲基第三丁基醚稀釋，使用廣效型流洗液流洗Si SPE cartridge搭配C18 SPE cartridge可達最佳之淨化效果，且可同時分析所有單氯丙二醇單酯（簡稱單酯）及單氯丙二醇雙酯（簡稱雙酯）待測物，單酯平均添加回收率為99~127%（重複分析相對差異百分比RPD為0~18%），雙酯平均添加回收率為75~119%（RPD為1~13%）。低脂食品類及高脂食品類使用乙酸乙酯進行高效率萃取，為了克服基質效應對於雙酯回收率之影響，以精準體積之窄效型流洗液流洗Si SPE cartridge搭配HLB SPE cartridge達最佳之淨化效果。低脂食品類之前處理流程可同時分析所有單酯及雙酯待測物，單酯之平均添加回收率為88~110%（RPD為1~16%），雙酯之平均添加回收率為83~113%（RPD為2~19%）；由於基質效應影響，高脂食品類之前處理流程則是分別分析單酯及雙酯，單酯平均添加回收率為77~102%（RPD為1~19%），雙酯平均添加回收率為83~113%（RPD為0~13%）。三大類基質之前處理方法具高度之準確性及穩定性，分析結果均符合本研究之品保品管規範。HPLC-ESI-MS/MS儀器條件測試結果顯示，流動相A（2mM甲酸銨及0.05%甲酸溶於75:25甲醇:水）搭配流動相B（2mM甲酸銨及0.05%甲酸溶於異丙醇）對於24種3-及2-MCPDEs之分離效果最佳，且能有效分離部分同分異構物。本方法開發完成後已完成37件市售加工食品中24種3-及2-MCPDEs之含量分析包括19件油脂類、8件其他食品類及10件嬰幼兒奶粉類，藉以驗證方法之可用性，37件樣品分析之品保品管數據均符合規範，顯示方法具可用性。37件樣品分析結果顯示，油脂類、嬰幼兒奶粉類及其他食品類3-MCPDEs（以3-MCPD當量表示）平均總含量分別為739 ng/g（49~2525 ng/g）、147 ng/g（ND~175 ng/g）及201 ng/g（ND~678 ng/g）；2-MCPDEs（以2-MCPD當量表示）平均總含量分別為75 ng/g（11~308 ng/g）、39 ng/g（ND~45 ng/g）及41 ng/g（ND~131 ng/g）。整體而言，三大類別食品中油脂類之檢出率及檢出濃度位居首位，其中3-MCPDEs總含量以米糠油最高，葡萄籽油次之，分別為2525 ng/g及2465 ng/g；而2-MCPDEs於各食品中之檢出濃度相對3-MCPDEs低。油脂類及其他食品類單酯檢出率以1Ol最高，分別為68%及50%，雙酯檢出率以Ol-St為最高，分別為100%及63%；而在嬰幼兒奶粉中單酯及雙酯檢出率則分別以1My之50%及Ol-Ol之60%最高。油脂類單酯檢出平均濃度以1Li最高，1Ol次之，濃度分別為95 ng/g及74 ng/g，而雙酯檢出平均濃度以Li-Li最高，Ol-Li次之，濃度分別為1425 ng/g及1250 ng/g。由以上結果顯示精煉植物油具有高度污染風險，且其廣泛應用於各種加工食品中，建議政府單位針對該類別進行含量監測外，對於相關之加工製品亦加強關注，以維護食品安全，保障國民健康。

3-monochloropropane-1,2-diol esters (3-MCPDEs) and 2-monochloropropane-1,2-diol esters (2-MCPDEs) are food processing contaminants mainly found in refined vegetable oils during heating-deodorization step(≥200°C) and related processed foods. The toxicity of 3- and 2-MCPDEs is concerned due to their potential transformation to free form, 3- and 2-MCPD, during digestion in the gastrointestinal tract. 3-MCPD may cause toxicological effects in the kidneys and reproductive systems as well as has been classified as possibly carcinogenic to humans (Group 2B) by the IARC. According to the limited studies, toxicological concerns related to 2-MCPD are different with 3-MCPD. Currently, the indirect analytical methods commonly used in the world by gas chromatography-mass spectrometry (GC/MS) have many limitations and uncertainties such as the formation of artifacts from hydrolysis or derivatization step and information about individual esters as they occur in foods is lacking. Therefore, the present study is aimed to develop a direct method to measure 18 kinds of 3-MCPDEs and 6 kinds of 2-MCPDEs congeners in commercial processed foods by high performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). Suitable pretreatment methods were developed for three food matrices (oils and fats, low-fat foods and high-fat foods) including extract and cleanup procedure. The extracts were then analyzed using HPLC-ESI-MS/MS and the analytical methods were validated by quality control and quality assurance guidelines. The pretreatment method results were shown that oils and fats were purified using two kinds of SPE cartridges (silica and C18). Low- and high-fat foods were effectively extracted by ethyl acetate and then purified using two SPE cartridges (silica and HLB). Chromatographic condition could separate effectively 24 target analytes even isomers involved 3-MCPDEs and 2-MCPDEs. The range of average recoveries across oil and fat, low-fat food and high-fat food matrices were 75−127%, 83−113% and 77−113% for 3- and 2-MCPDEs, respectively. Repeatability expressed as relative percent difference (RPD%) of each analytes were below 20%. The preliminary detection survey of 37 commercial products including oils and fats, infant formulas and other foods was shown that oils and fats had the highest contamination which concentrations for 3-MCPDEs (expressed as 3-MCPD equivalents) and 2-MCPDEs (expressed as 2-MCPD equivalents) ranged from 49 to 2525 ng/g (739 ng/g) and from 11 to 308 ng/g (75 ng/g), respectively. The highest level of 3-MCPDEs was found in rice bran oil (2525 ng/g), followed by grapeseed oil (2465 ng/g). There were lower concentrations of 3- and 2-MCPDEs in infant formulas and other foods. In the high contaminated oil and fats, 1Ol (68%) and Ol-St (100%) was the most abundant MCPD mono-esters and MCPD di-esters, respectively. In addition, the highest average level of the MCPD mono-esters was 1Li (95 ng/g), followed by 1Ol (74 ng/g) and the highest average level of the MCPD di-esters was Li-Li (1425 ng/g), followed by Ol-Li (1250 ng/g). The present study found that 1Ol, 1Li, Li-Li and Ol-Li were dominant congeners in vegetable oils and fats, may cause human potential health risk. We recommended government that not only strengthened monitor and mitigation actions of vegetable oils and fats contaminations but also paid attention to related processed food products.

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