3-Aminopropanamide (3-APA) is the direct precursor of acrylamide produced in the Maillard reaction between asparagine and reducing sugars. In this research, we found that 3-APA could reduce acrylamide by the formation of adducts between acrylamide and 3-APA via Michael addition. The effects of temperature, heating duration and 3-APA/acrylamide ratio on the reduction of acrylamide were investigated. Addition of 3-APA to acrylamide at a molar ratio of 5:3 at 160 °C for 20 min reduced acrylamide by up to 47.29%. The major adduct was identified as 3,3',3'-nitrilotris, and its cytotoxicity on Caco-2 cells was evaluated to be much lower than acrylamide. The viability of Caco-2 cells retained at 88.31% and 86.43% after incubation with 16 mM 3,3',3'-nitrilotris for 24 and 48 hr, respectively, while those incubated with the same concentration of acrylamide were 23.33% and 19.12%, respectively. PRACTICAL APPLICATION The current study reported 3-APA could reduce acrylamide through the Micheal addition reaction between 3-APA and acrylamide. The adduct showed significantly reduced cytotoxicity compared to acrylamide. The research is critical in evaluation and control of food contaminants. The results brought new insights in the area of food safety, especially in the mechanism researches on formation and mitigation of endogenous contaminants in thermal-processed foods.

中文翻译：

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热处理过程中同时发生3-氨基丙酰胺生成和还原丙烯酰胺

3-氨基丙酰胺 (3-APA) 是天冬酰胺和还原糖之间的美拉德反应中产生的丙烯酰胺的直接前体。在这项研究中，我们发现 3-APA 可以通过迈克尔加成在丙烯酰胺和 3-APA 之间形成加合物来还原丙烯酰胺。考察了温度、加热时间和3-APA/丙烯酰胺比对丙烯酰胺还原的影响。在 160 °C 下以 5:3 的摩尔比将 3-APA 添加到丙烯酰胺中 20 分钟，丙烯酰胺减少了高达 47.29%。主要加合物被确定为 3,3',3'-次氮基三醇，其对 Caco-2 细胞的细胞毒性被评估为远低于丙烯酰胺。Caco-2 细胞在与 16 mM 3,3',3'-次氮三醇孵育 24 小时和 48 小时后分别保持在 88.31% 和 86.43% 的存活率，而用相同浓度的丙烯酰胺孵育的分别为23.33%和19.12%。实际应用 目前的研究报道，3-APA 可以通过 3-APA 和丙烯酰胺之间的迈克尔加成反应减少丙烯酰胺。与丙烯酰胺相比，该加合物显示出显着降低的细胞毒性。该研究对于评估和控制食品污染物至关重要。研究结果为食品安全领域，特别是热处理食品中内源性污染物的形成和减缓机理研究带来了新的认识。该研究对于评估和控制食品污染物至关重要。研究结果为食品安全领域，特别是热处理食品中内源性污染物的形成和减缓机理研究带来了新的认识。该研究对于评估和控制食品污染物至关重要。研究结果为食品安全领域，特别是热处理食品中内源性污染物的形成和减缓机理研究带来了新的认识。