N,N'-disubstituted guanidine high-potency sweeteners.
The role and function of the aryl group in the highly potent trisubstituted guanidine sweeteners 7a-d was investigated. Four disubstituted guanidines, lacking the aryl group, were prepared. These guanidines contain a hydrophobic substituent on one nitrogen and a carboxymethyl group substituted on one of the other nitrogens. They were found to be tasteless or to have a significantly lower sweetness potency than the corresponding trisubstituted compounds. Possible rationales for the effects of structure on the sweet taste activity are discussed.
Muller
G W
GW
Research & Development, NutraSweet Company, Mt. Prospect, Illinois 60056.
Walters
D E
DE
DuBois
G E
GE
D000813:Anilides / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D006146:Guanidines / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000737:chemistry*; D013649:Taste; D014508:Urea / Q000737:chemistry
D000813:Anilides; D000814:Aniline Compounds; D006146:Guanidines; D013549:Sweetening Agents; D014508:Urea