A novel sweetener with extremely sweetness potency, N-[N-3-(2-hydroxy-4-methyl-phenyl) propyl-α-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-α-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.

European Food Research and Technology

Biotechnology; Chemistry; Analytical Chemistry; Food Science; Sweetness potency; Forestry; Agriculture; Sweetener; N -[ N -3-(2-hydroxy-4-methylphenyl) propyl-α-aspartyl]- l -phenylalanine-1-methylester; Palladium; Raw materials; Chemical properties; Phenylalanine; Analysis

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