基于十二碳烯醛的番茄红素全合成  

Total synthesis of lycopene based on dodecatrienal

作　　者：陈果 晏日安[1] 黎海梅 周华[1] 李存芝[1] CHEN Guo;YAN Ri-an;LI Hai-mei;ZHOU Hua;LI Chun-zhi(Department of Food Science and Engineering,Jinan University,Guangzhou,Guangdong 510632,China)

机构地区：[1]暨南大学食品科学与工程系,广东广州510632

出　　处：《食品与机械》2021年第3期162-167,共6页Food and Machinery

基　　金：广东省科技计划项目(编号:201903010070)。

摘　　要：以6,10-二甲基-3,5,9-十一烷三烯-2-酮(8)与亚甲基二磷酸四乙酯(7)经Wittig-Horner反应得到2,6,10-三甲基-1,3,5,9-四烯十一烷基膦酸二乙酯(9);以E-2-丁烯-1,4-二膦酸二乙酯(2)与4,4-二甲氧基-2-丁酮(3)通过Wittig-Horner反应和水解反应合成化合物3,8-二甲基-3,5,7-辛三烯-1,10-二醛(5),2,6,10-三甲基-1,3,5,9-四烯十一烷基膦酸二乙酯(9)与3,8-二甲基-3,5,7-辛三烯-1,10-二醛(5)通过Wittig-Horner反应得到目标产物番茄红素(10),并采用核磁共振(NMR)、质谱(HRMS/GC-MS)和红外光谱(IR)进行结构验证。结果表明,合成的番茄红素总产率为16.7%。Diethyl[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]phosphonate(9)was synthesized via a condensation between tetraethyl methylenebis(phosphonate)(7)and 6,10-dimethyl-3,5,9-undecatrien-2-one(8)by Wittig-Horner reaction,(3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial(5)was prepared from(E)-tetraethyl but-2-ene-1,4-diylbis-(phosphonate)(2)and 4,4-dimethoxy-2-butanone(3)by Wittig-Horner reaction followed by hydrogenation.Lycopene was synthesized from diethyl[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]phosphonate(9)and(3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial(5)by Wittig-Horner reaction,the structure of products was confirmed by NMR,HRMS/GC-MS and IR techniques.The total yield was 16.7%.

关 键 词：十二碳烯醛 WITTIG-HORNER反应 番茄红素 全合成 

分 类 号：TS264.4[轻工技术与工程—发酵工程]