Contribution of 1,2-Dihydroxy-5-(methylsuifinyl)pentan-3-one (DMTS-P1) to the Formation of Dimethyl Trisulfide (DMTS) during the Storage of Japanese Sake

被引:24
作者
Isogai, Atsuko [1 ]
Kanda, Ryoko [1 ]
Hiraga, Yoshikazu [2 ]
Iwata, Hiroshi [1 ]
Sudo, Shigetoshi [1 ]
机构
[1] Natl Res Inst Brewing, Higashihiroshima 7390046, Japan
[2] Hiroshima Univ, Grad Sch Sci, Dept Chem, Higashihiroshima 7398526, Japan
关键词
Dimethyl trisulfide; DMTS; 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one; DMTS-P1; sake; hineka; LC-MS/MS; IDENTIFICATION; ODORANTS; FLAVOR;
D O I
10.1021/jf100707a
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Dimethyl trisulfide (DMTS) is involved in the unpalatable aroma of stale Japanese sake, called "hineka". Recently, we isolated one of the precursor compounds of DMTS in sake and identified it as 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one (DMTS-P1), a previously unknown compound. In this work, the contribution of DMTS-P1 to the formation of DMTS was investigated. DMTS-P1 was chemically synthesized from methional in three steps, consisting of the Grignard reaction, followed by oxidation by MnO(2) and an immobilized osmium oxide catalyst. The formation of synthetic DMTS-P1 was confirmed by a comparison of the liquid chromatography mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) data to that of natural DMTS-P1. Quantitative analysis of DMTS-P1 in sake was developed using LC-MS/MS, and a positive correlation was observed between the concentration of DMTS-P1 in sake and the production of DMTS during storage. These results indicate that DMTS-P1 contributes to the formation of DMTS in sake.
引用
收藏
页码:7756 / 7761
页数:6
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