title: Practical large-scale production of dihydrocapsiate, a nonpungent capsaicinoid-like substance.
abstract: Capsinoids represent a novel group of capsaicinoid-like substances found in a nonpungent cultivar, Capsicum annuum "CH-19 Sweet." They have capsaicinoid-like physiological and biological properties while lacking the harmful stimuli of capsaicinoids. A large-scale synthesis of dihydrocapsiate (DCT) is established in this work. 8-Methynonanoic acid (MNA) was synthesized by copper-catalyzed cross-coupling of ethyl 6-bromohexanoate with isobutylmagnesium bromide and subsequent hydrolysis. Lipase-catalyzed chemoselective esterification of vanillyl alcohol and MNA was performed at 50 °C under reduced pressure to remove water without solvents or drying agents. A slightly larger stoichiometric amount of MNA was used and the purification in the final stage was simplified to leave a small amount of MNA in the product, because we found that the presence of a small amount of MNA is necessary to stabilize DCT. DCT was synthesized according to the production, and stabilization methods described here has been filed as a new dietary ingredient.
authors.affiliation: a Institute for Innovation, Ajinomoto Co., Inc. , Kawasaki , Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Kurosawa
authors.affiliation: b Tokai Plant, Ajinomoto Co., Inc. , Yokkaichi , Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakano
authors.affiliation: a Institute for Innovation, Ajinomoto Co., Inc. , Kawasaki , Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Amino
mesh_terms: D001592:Benzyl Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005227:Fatty Acids / Q000138:chemical synthesis / Q000737:chemistry; D005502:Food
chemical_list: D001592:Benzyl Alcohols; D005227:Fatty Acids; C529521:isodihydrocapsiate; C008776:pelargonic acid; D002211:Capsaicin; C024078:vanillyl alcohol
keywords: 8-methynonanoic acid; capsinoid; dihydrocapsiate; lipase-catalyzed esterification; vanillyl alcohol