Determination of the absolute configuration of a novel odour-active lactone,cis-3-methyl-4-decanolide, in wasabi (Wasabia japonicaMatsum.)

Autor: Kenji Haraguchi, Takashi Nammoku, Akira Nakanishi, Norio Miyazawa, Yoshiko Kurobayashi, Hiroyuki Watanabe
Rok vydání: 2014
Předmět:
Zdroj: Flavour and Fragrance Journal. 29:220-227
ISSN: 0882-5734
Popis: The aroma of freshly grated wasabi (Wasabia japonica Matsum.) is not only pungent but also sweet, fruity, green and creamy. In this study we investigated wasabi aroma concentrate by aroma extract dilution analysis. Ten odorants were detected as odour-active compounds at the highest flavour dilution factors of 256 and 1024: 3-methyl-2-butene-1-thiol, allyl isothiocyanate, (Z)-1,5-octadien-3-one, 2-isopropyl-3-methoxypyrazine, 4-pentenyl isothiocyanate, 5-hexenyl isothiocyanate, 3-methyl-2,4-nonanedione, cis-3-methyl-4-decanolide, 6-(methylthio)hexyl isothiocyanate, and vanillin. Among them, (Z)-1,5-octadien-3-one and cis-3-methyl-4-decanolide were identified for the first time in wasabi. To determine the absolute stereochemistry of cis-3-methyl-4-decanolide in wasabi, we synthesized the stereoisomers of 3-methyl-4-decanolide from optically active γ-decalactone. Finally, the absolute configurations of cis-3-methyl-4-decanolide were determined as (3R,4R)-3-methyl-4-decanolide by matching the retention time and odour qualities in chiral GC-MS. Copyright © 2014 John Wiley & Sons, Ltd.
Databáze: OpenAIRE