Screening and identification of precursor compounds of dimethyl trisulfide (DMTS) in Japanese sake

J Agric Food Chem. 2009 Jan 14;57(1):189-95. doi: 10.1021/jf802582p.

Abstract

Dimethyl trisulfide (DMTS) is involved in the unpalatable aroma of stale sake, called "hineka"; however, the mechanism underlying the formation of DMTS during the storage of sake has not been elucidated. This paper investigates the precursors of DMTS in sake. An experiment using [methyl-d(3)]-methionine showed that Strecker degradation of methionine plays a minor role in the formation of DMTS. Separation of components in sake by cation exchange resin revealed that DMTS precursors are present in the acidic/neutral fraction rather than in the basic one. Purification of the DMTS precursor compounds was carried out through several chromatographic steps, measuring DMTS-producing potential as an index. High-resolution ESI-MS and 1D/2D NMR experiments enabled the identification of one of the precursor compounds as 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one.

MeSH terms

  • Alcoholic Beverages / analysis*
  • Japan
  • Magnetic Resonance Spectroscopy
  • Odorants / analysis*
  • Pentanones / analysis
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfides / analysis*
  • Sulfides / chemistry*

Substances

  • 1,2-dihydroxy-5-(methylsulfinyl)pentan-3-one
  • Pentanones
  • Sulfides
  • dimethyl trisulfide