title: New Umami Amides: Structure-Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in Zanthoxylum piperitum.
abstract: A series of aromatic amides were synthesized from various acids and amines selected from naturally occurring structural frameworks. These synthetic amides were evaluated for umami taste in comparison with monosodium glutamate. The effect of the substitution pattern of both the acid and the amine parts on umami taste was investigated. The only intensely umami-tasting amides were those made from 3,4-dimethoxycinnamic acid. The amine part was more tolerant to structural changes. Amides bearing an alkyl- or alkoxy-substituted phenylethylamine residue displayed a clean umami taste as 20 ppm solutions in water. Ultraperformance liquid chromatography coupled with a high quadrupole-Orbitrap mass spectrometer (UPLC/MS) was subsequently used to show the natural occurrence of these amides. (E)-3-(3,4-Dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide was shown to occur in the roots and stems of Zanthoxylum piperitum, a plant of the family Rutaceae growing in Korea, Japan, and China.
authors.forename: Eric
authors.initials: E
authors.lastname: Frerot
authors.forename: Nathalie
authors.initials: N
authors.lastname: Neirynck
authors.forename: Isabelle
authors.initials: I
authors.lastname: Cayeux
authors.affiliation: ‡Firmenich Aromatics (China) Co., Ltd., No. 3901 JinDu Road, Xinzhuang Industry Park, Shanghai 201108, China.
authors.forename: Yoyo Hui-Juan
authors.initials: YH
authors.lastname: Yuan
authors.affiliation: ‡Firmenich Aromatics (China) Co., Ltd., No. 3901 JinDu Road, Xinzhuang Industry Park, Shanghai 201108, China.
authors.forename: Yong-Ming
authors.initials: YM
authors.lastname: Yuan
mesh_terms: D000577:Amides / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry*; D005421:Flavoring Agents / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry*; D013649:Taste; D032106:Zanthoxylum / Q000737:chemistry*
chemical_list: D000577:Amides; D002934:Cinnamates; D005421:Flavoring Agents; D010936:Plant Extracts; C029010:cinnamic acid
keywords: UPLC/MS; Zanthoxylum piperitum; aromatic amides; umami taste