Behaviors of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate during Brewing Processes

Kishimoto, Toru; Morimoto, Masahito; Kobayashi, Minoru; Yako, Nana; Wanikawa, Akira

doi:10.1094/asbcj-2008-0702-01

Cited by 36 publications

(71 citation statements)

References 12 publications

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“…Actually, the presence of copper in this type of treatment might oxydize a part of thiol into the corresponding disulfides or metal‐complexes. In the same time, it has been hypothesized the occurrence of thiol precursors in both malts and hops for the first time. Few years later, the S ‐cysteinylated precursor of 3MH (Cys3MH) was formally identified by High Resolution Mass Spectrometry (HRMS) in Cascade hop variety .…”

Section: Introductionmentioning

confidence: 99%

First identification and quantification of glutathionylated and cysteinylated precursors of 3‐mercaptohexan‐1‐ol and 4‐methyl‐4‐mercaptopentan‐2‐one in hops (Humulus lupulus)

Roland¹,

Viel²,

Reillon³

et al. 2016

Flavour & Fragrance J

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Since ten years, many studies conducted on beers showed an important impact of polyfunctionnal thiols of the aroma profiles. Among them, three thiols responsible for blackcurrant bud, passion fruit, citrus and rhubarb notes have been intensively studied: the 4‐methyl‐4‐mercaptopentan‐2‐one (4MMP), the 3‐mercaptohexan‐1‐ol (3MH) and its corresponding acetate. Their origin was very complex in beers since they probably came from odourless precursors present either in hops or in malts. Our work focused on the formal identification of thiol precursors in hops and on their quantification. By using pure synthetic standards and mass spectrometry characterization, we formally identified for the first time the occurrence of glutathionylated conjugates of 4MMP and 3MH and the cysteinylated conjugate of 4MMP in hops. First quantification results obtained on 10 hop varieties, showed that 3MH conjugates were more ubiquitous than 4MMP ones. Conjugates of 3MH occurred at very high level until 20 mg kg‐1 in Cascade hop, which was considerably higher than concentrations found in grapes. Then, we compared the proportion of bound and free thiol fractions and we demonstrated that more than 99 % of 3MH occurred as precursors in hops. On the contrary, free 4MMP fraction represented the most important source of 4MMP in hops. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

First identification and quantification of glutathionylated and cysteinylated precursors of 3‐mercaptohexan‐1‐ol and 4‐methyl‐4‐mercaptopentan‐2‐one in hops (Humulus lupulus)

Roland¹,

Viel²,

Reillon³

et al. 2016

Flavour & Fragrance J

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“…Hop is the main contributor of thiols to beer (21)(22)(23)(24)(25). The compounds 3-sulphanyl-4-methylpentan-1-ol, 3-sulphanyloctan-1-ol, and 3-sulphanylhexan-1-ol distinguish Nelson Sauvin-, Tomahawk-, and Cascade-hopped beers, respectively (21,25,26).…”

Section: Introductionmentioning

confidence: 99%

“…The compounds 3-sulphanyl-4-methylpentan-1-ol, 3-sulphanyloctan-1-ol, and 3-sulphanylhexan-1-ol distinguish Nelson Sauvin-, Tomahawk-, and Cascade-hopped beers, respectively (21,25,26). Although already found in hop, significant amounts of free thiols continue to be produced through wort boiling and fermentation (21,23,25).…”

Section: Introductionmentioning

confidence: 99%

Enzymatic release of odourant polyfunctional thiols from cysteine conjugates in hop

2013

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Polyfunctional thiols are contributors to the hop varietal aroma of beer. Besides free thiols, a cysteine-S-conjugate has recently been shown to be an additional component of the thiol potential of hop. Such cysteine adducts investigated here in four hop cultivars and in different hop forms. Hop hydroalcoholic extracts were purified on a cation exchanger and subjected to apotryptophanase β-lyase activity. The Cascade hop variety exhibited the highest bound 3-sulphanylhexan-1-ol (grapefruit-like) potential, while both Tomahawk and Nelson Sauvin cultivars were confirmed to be important sources of bound 3-methyl-2-butene-1-thiol (skunky-like), 3-sulphanylpentan-1-ol and 4-sulphanyl-4-methylpentan-2-one (box-tree-like). Surprisingly, hop CO 2 extracts proved to contain cysteine conjugates. Although related, the concentrations of cysteine-bound thiols in hop are not strictly correlated to the amounts of free volatiles found in the derived beers.

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“…Polyfunctional thiols exist in free form in hop pellets (9)(10)(11)(12), but are also formed during boiling and fermentation, and this suggests the presence of precursors in malt or hop (9)(10)(11). In wine, the presence of cysteinylated and glutathionylated precursors has been shown (13)(14)(15), and the same precursors are suspected in hop (16).…”

Section: Introductionmentioning

confidence: 99%

“…4‐Sulphanyl‐4‐methylpentan‐2‐one (4S4M2Pone) confers a box‐tree fruity character to lager beer . 3‐Sulphanylhexan‐1‐ol (3SHol), 3‐sulphanylhexyl acetate (3SH‐A) and 1‐sulphanylpentan‐3‐ol (1S3Pol) are also found in most lager beers . 3‐Sulphanyl‐4‐methylpentan‐1‐ol (3S4MPol) and 3‐sulphanyl‐4‐methylpentyl acetate (3S4MP‐A) have been evidenced in beer hopped with the Nelson Sauvin cultivar , while in Tomahawk‐hopped beers, Gros et al have shown that 3SHol, 3‐sulphanyloctan‐1‐ol (3SOol), 4S4M2Pone, 3S4MPol and 3‐sulphanyl‐2‐ethylpropyl acetate (3S2EPr‐A) most probably exceed their threshold values.…”

Section: Introductionmentioning

confidence: 99%

Fate of 2-sulphanylethyl acetate and 3-sulphanylpropyl acetate through beer aging

et al. 2012

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Sulphanylalkyl alcohols and their corresponding acetates were investigated in 14 commercial Belgian beers. Although it was the major peak at the pulsed-flame photometric detector, the empyreumatic 2-sulphanylethyl acetate was found at concentrations below its individual odour threshold, estimated at 40 mg/L (0-4 mg/L in most fresh beers, 5-12 mg/L in three fresh high-bitter beers). Both the Ehrlich pathway and hop constituents contribute to this content. In 11 of the investigated samples, synthesis of 2SE-A and 3-sulphanylpropyl acetate (roasted, burned) continued during the first three months of storage. Although below their individual thresholds, these compounds might interact by synergy with other aged flavours. As yeast was absent from most of the investigated bottles, chemical degradation of precursors is suspected.

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Behaviors of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate during Brewing Processes

Cited by 36 publications

References 12 publications

First identification and quantification of glutathionylated and cysteinylated precursors of 3‐mercaptohexan‐1‐ol and 4‐methyl‐4‐mercaptopentan‐2‐one in hops (Humulus lupulus)

First identification and quantification of glutathionylated and cysteinylated precursors of 3‐mercaptohexan‐1‐ol and 4‐methyl‐4‐mercaptopentan‐2‐one in hops (Humulus lupulus)

Enzymatic release of odourant polyfunctional thiols from cysteine conjugates in hop

Fate of 2-sulphanylethyl acetate and 3-sulphanylpropyl acetate through beer aging

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