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

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 13; pp. 7756 - 7761
• Main Authors: Isogai, Atsuko, Kanda, Ryoko, Hiraga, Yoshikazu, Iwata, Hiroshi, Sudo, Shigetoshi
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 14-07-2010
• Subjects: 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one; Biological and medical sciences; Chemical Changes Induced by Processing/Storage; dimethyl trisulfide; Food Handling; Food industries; food storage; freshness; Fundamental and applied biological sciences. Psychology; off odors; palatability; Pentanones - chemical synthesis; Pentanones - chemistry; sake; storage quality; Sulfides - chemistry; Wine - analysis; wine quality; DMTS-P1; DMTS; Dimethyl trisulfide; 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one; sake; hineka; LC−MS/MS; LC-MS/MS; Warehousing; Food preservation; Liquid chromatography; Sake
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf100707a

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 MnO2 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.