Chapter 8B
Polyfunctional Thiol Compounds
Denis Dubourdieu and Takatoshi Tominaga
Contents
8B.1 Introduction...................... ........................................ 275
8B.2 Volatile Thiols Involved in the Varietal Aromas of Wine................... ...... 276
8B.3 StereoisomericDistributionof3-Sulfanylhexan-1-ol anditsAcetate ............... 281
8B.4 Other Volatile Thiols also Contribute a Variety of Aromatic Nuances to Wines ...... 283
8B.5 Precursors of Volatile Thiols Derived from Cysteine...................... ...... 286
References ............................................................... 290
8B.1 Introduction
Sulfur compounds, and especially volatile thiols, are extremely odoriferous
molecules, which contribute to the aromas of many fruits, plants, and foods
(Shankaranarayana et al. 1982). For example, certain thiols contribute to the char-
acteristic aroma of blackcurrant (Rigaud et al. 1986), grapefruit (Demole et al. 1982;
Buettner and Schieberle 1999), passion fruit (Engel and Tressl 1991), guava (Idstein
and Schreier 1985), and fringed rue (Ruta chalepensis) (Escher et al. 2006). The key
role played by thiols in the odor of roasted coffee (Tressl and Silwar 1981), popcorn,
and grilled meat is also well known (Gasser and Grosch 1988; Guth and Grosch 1994;
Schieberle 1991). Finally, the contribution of compounds in this family to the aroma
of beer was recently reported (Vermeulen et al. 2006; Takoi et al. 2007).
In wine, sulfur compounds (including thiols) were initially exclusively associated
with fetid, nauseating odors, mainly due to molecules such as hydrogen sulfide,
methanethiol, ethanethiol, and methionol. The involvement of sulfur compounds in
the pleasant herbaceous, fruity, mineral, smoky, and toasty aromas of wine was only
detected at a later stage, thanks to a specific method for purifying volatile thiols,
usingp-hydroxymercuribenzoic acid (p-HMB) (Tominaga et al. 1998a; Tominaga
and Dubourdieu 2006).
D. Dubourdieu (B)
Universit ́e Victor Segalen Bordeaux 2, Facult ́e d’ Œnologie, UMR, Œnologie, INRA, Institut des
Sciences de la Vigne et du Vin, 351 cours de la Lib ́eration, 33405 Talence Cedex, France
e-mail: [email protected]
M.V. Moreno-Arribas, M.C. Polo (eds.),Wine Chemistry and Biochemistry,
DOI 10.1007/978-0-387-74118-512,©CSpringer Science+Business Media, LLC 2009
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