Synthesis and characterization of a novel sweetener with high sweetness strength.

摘要

A novel sweetener with extremely sweetness potency, N-[N-3-(2-hydroxy-4-methyl-phenyl) propyl- alpha -aspartyl]-l-phenylalanine-1-methylester, was synthesized through a new synthetic method. 7-methylcoumarin was used as the raw material to synthesize 2-hydroxy-7-methylchroman, an important intermediate, by reduction reaction catalyzed by palladium-carbon and dialuminum hydride. The prepared 2-hydroxy-7-methylchroman then reacted with aspartame through carbonyl-amino condensation reaction and reduction reaction. The yield was approximately 58%; results of FTIR, EI-MS, and NMR confirmed that the product was N-[N-3-(2-hydroxy-4-methylphenyl) propyl- alpha -aspartyl]-l-phenylalanine-1-methylester. The synthesized sweetener was a B₁, B₂, AH₁, XH₂, G₁, E₁, G₂, E₂, G₃, G₄-type sweetener shown by constructed multipoint attachment model, which well explained why the synthesized sweetener presented so formidable sweetness potency.