一种新型纽甜类似物甜味剂的合成及表征

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  • (暨南大学 食品科学与工程系,广东 广州,510632)

网络出版日期: 2018-07-04

基金资助

广东省科技计划项目(2016B020204002)

Synthesis and characterization of a novel sweetener about neotame derivatives

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  • (Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China)

Online published: 2018-07-04

摘要

为合成新型二肽类甜味剂,以甲醇、3,3-二甲基丙烯酸为初始原料,经Fischer酯化反应得到3,3-二甲基丙烯酸甲酯,再与2,5-二甲酚、甲烷磺酸发生Friedel-Crafts烷基化反应得到4,4,5,8-四甲基-3,4-二氢香豆素,产物以LiAlH4为还原剂还原得到3-(2-羟基-3,6-二甲基苯基)-3-甲基丁醇,经2步保护反应分别保护醇羟基和酚羟基之后,用CH3COOH脱掉叔丁基二甲基硅基(TBS)得到乙酰基保护的醇,用Dess-Martin periodinane氧化醇得到纽甜类似物的中间体3-(2-乙酰基-3,6-二甲基苯基)-3-甲基丁醛,最后将中间体与阿斯巴甜在硼氢化钠(NaBH4)的还原胺化作用下合成高倍甜味剂纽甜类似物N-[N-[3-(2-乙酰基-3,6-二甲基苯基)-3-甲基丁基]-L-α-天冬氨酰]-L-苯丙氨酸1-甲酯。采用红外光谱(IR)、质谱(MS)以及核磁共振(NMR)对终产物进行结构鉴定和表征,结果确定其为目标终产物,并测得其甜度约为蔗糖的70 000倍。

本文引用格式

李艳波, 马亚茹, 胡南, 等 . 一种新型纽甜类似物甜味剂的合成及表征[J]. 食品与发酵工业, 2018 , 44(5) : 96 -103 . DOI: 10.13995/j.cnki.11-1802/ts.016661

Abstract

To synthesis of the novel dipeptide sweetener, using methanol and 3,3-dimethylanrylic acid as starting materials, concentrated sulfuric acid as a catalyst, then through Fischer-Speier esterification to synthesis 3,3-dimethylacrylate, then 2,5-dimethylphenol was treated with 3,3-dimethylacrylate in the presence of methanesulfonic acid to give 4,4,5,8-tetramethyl-3,4-dihydroguccin through Friedel-Crafts acylation.A solution of previous compound added to lithium aluminium hydride to give 3-(2-hydroxy-3,6-dimethylphenyl)-3-methylbutanol, after two steps to protected the alcoholic hydroxyl and phenolic hydroxyl, then acetic acid eliminated the tertbutyldimethylsilyl that could obtain the alcohol which protected by acetyl.The alcohol was oxidation by Dess-Martin periodinane and give the intermediate about neotame derivatives is 3-(2-acetyl-3,6-dimethylphenyl)-3-methylbutyraldehyde.Finally, the intermediate combined with aspartame though Borch reduction by sodium borohydride, the final product N-[N-[3-(2-acetyl-3,6-dimethylphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanie1-methyl ester was obtained, Using Infrared spectroscopy(IR), ESImass spectrometry(MS)and nuclear magnetic resonance spectroscopy(NMR) for structure identification and characterization, and the final product was a target compound and could reach about 70,000 times higher than sucrose.
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