Rottmann Eric, Volkmann Kristina, Fohrer Jörg, Krings Ulrich, Berger Ralf G
Gottfried Wilhelm Leibniz Universität Hannover, Institut für Lebensmittelchemie, Callinstraße 5, 30167, Hannover, Germany.
Gottfried Wilhelm Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, 30167, Hannover, Germany.
Curr Res Food Sci. 2021 Apr 19;4:262-269. doi: 10.1016/j.crfs.2021.04.005. eCollection 2021.
Three phenolic acids, -coumaric, ferulic and caffeic acid as well as cinnamic acid were added to raw potatoes and sweet potatoes before frying. A distinct mitigation of acrylamide was not detected. Fried samples were analysed for postulated adducts of a direct reaction between acrylamide and these phenolic acids using LC-MS. In a model system with pure compounds (phenylacrylic acid and acrylamide) heated on 10% hydrated silica gel one specific adduct (respective m/z for M + H) was formed in each reaction. MS/MS-data suggested an oxa-Michael formation of 3-amino-3-oxopropyl-phenylacrylates, which was confirmed by syntheses along an S2 substitution of 3-chloropropanamide. Exemplarily, the structure of the ester was confirmed for -coumaric acid by NMR-data. Standard addition revealed that 3-amino-(3-oxopropyl-phenyl)-acrylates occurred neither in fried potato nor in sweet potato, while a formation was shown in phenylacrylic acid plus acrylamide supplemented potatoes and sweet potatoes.
在油炸之前，将三种酚酸，即对香豆酸、阿魏酸、咖啡酸以及肉桂酸添加到生土豆和红薯中。未检测到丙烯酰胺有明显减少。使用液相色谱 - 质谱联用仪（LC-MS）对油炸样品中丙烯酰胺与这些酚酸直接反应的假定加合物进行了分析。在一个含有纯化合物（苯丙烯酸和丙烯酰胺）并在10%水合硅胶上加热的模型系统中，每个反应都形成了一种特定的加合物（M + H的相应质荷比）。串联质谱（MS/MS）数据表明形成了3-氨基-3-氧代丙基-苯基丙烯酸酯的氧杂迈克尔加成物，这通过3-氯丙酰胺的S2取代合成得到了证实。例如，通过核磁共振（NMR）数据确定了对香豆酸酯的结构。标准加入法表明，3-氨基-（3-氧代丙基-苯基）-丙烯酸酯既未出现在油炸土豆中，也未出现在红薯中，而在添加了苯丙烯酸和丙烯酰胺的土豆和红薯中显示有形成。
