Category: sweetener
Aliases: E969, ANS9801, advantame acid precursor, N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-alpha-aspartyl]-L-phenylalanine 1-methyl ester
Advantame is a high-intensity, non-nutritive sweetener formed by reductive alkylation of [[aspartame]] with an isovanillin-derived (3-hydroxy-4-methoxyphenyl)propyl group, yielding a methyl-ester dipeptide derivative roughly 20,000 times sweeter than sucrose and ~110 times sweeter than aspartame. Sweetness arises from agonism at the heterodimeric T1R2/T1R3 sweet-taste GPCR on lingual taste cells, transduced via gustducin/PLCĪ²2 and TRPM5. Because it is effective at microgram-to-milligram levels, it is functionally non-caloric and does not raise [[glucose]] or [[insulin]]. It is poorly absorbed; the carboxymethyl ester is hydrolysed by intestinal esterases to advantame acid (de-esterified advantame), the principal faecal metabolite, with trace liberation of methanol and phenylalanine that is negligible at use levels.