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Determination of the absolute configuration of a novel odour‐active lactone, cis ‐3‐methyl‐4‐decanolide, in wasabi ( Wasabia japonica Matsum.)
Author(s) -
Nakanishi Akira,
Miyazawa Norio,
Haraguchi Kenji,
Watanabe Hiroyuki,
Kurobayashi Yoshiko,
Nammoku Takashi
Publication year - 2014
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3196
Subject(s) - chemistry , aroma , isothiocyanate , allyl isothiocyanate , vanillin , absolute configuration , stereochemistry , organic chemistry , food science
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 (3 R ,4 R )‐3‐methyl‐4‐decanolide by matching the retention time and odour qualities in chiral GC‐MS. Copyright © 2014 John Wiley & Sons, Ltd.