title: Asymmetric synthesis and sensory evaluation of sedanenolide.
abstract: The synthesis and sensory evaluation of enantiomeric sets of sedanenolide (1) and 3-butylphthalide (3) are described. The asymmetric synthesis was achieved via the intramolecular Diels-Alder reaction of chiral propargylester (5) which was prepared from optically active propargyl alcohol (4) and 2,4-pentadienoic acid. The sensory evaluation of these enantiomers revealed that there were distinct differences between their aroma character and odor threshold.
authors.affiliation: Technical Research Institute, R&D Center, T. Hasegawa Co., Ltd, Nakahara-ku, Kawasaki, Kanagawa, Japan.
authors.forename: Daichi
authors.initials: D
authors.lastname: Oguro
authors.forename: Hidenori
authors.initials: H
authors.lastname: Watanabe
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000077102:Apium / Q000737:chemistry*; D001572:Benzofurans / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005503:Food Additives / Q000032:analysis / Q000138:chemical synthesis*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis*; D020005:Propanols / Q000737:chemistry; D012684:Sensory Thresholds / Q000502:physiology*; D013237:Stereoisomerism; D013649:Taste; D055697:Taste Perception
chemical_list: D000480:Alkynes; D001572:Benzofurans; D005503:Food Additives; D020005:Propanols; C045855:3-N-butyl-4,5-dihydrophthalide; C027125:3-n-butylphthalide; C028255:propargyl alcohol