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

Tran, Thi Thu Hang; Gros, Jacques; Bailly, Sabine; Nizet, Sabrina; Collin, Sonia

doi:10.1002/jib.24

Cited by 11 publications

(15 citation statements)

References 29 publications

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“…Moreover, in Fig. (h) the significant downtrends in 3‐methylthiopropoanaldehyde and 3‐methylthiopropanol, as two effective precursors for the synthesis of DMTS during beer aging, would also imply that 3‐methylthiopropoanaldehyde and 3‐methylthiopropanol contribute to the stronger ‘caramel‐like’ aroma in aged Chinese rice wine. However, all predictions above should be verified further.…”

Section: Resultsmentioning

confidence: 99%

Characterization of volatile organic compounds as potential aging markers in Chinese rice wine using multivariable statistics

2019

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BACKGROUND There is a close relationship between certain ‘aging markers’ in wine and the wine's age. This study aimed to characterize all extracted aging markers in Chinese rice wine and distinguish the ages of Chinese rice wine using principal component analysis (PCA) and cluster analysis (CA). RESULTS A total of 49 potential aging markers (P ≤ 0.05*) were extracted from 71 volatile organic compounds (VOCs) in Chinese rice wine across a range of seven different ages. Of all 49 extracted aging markers, all furans, 2/3 aldehydes and ketones maintained significantly increasing levels with age (P ≤ 0.01**), especially sotolon (0.981**) and acetophenone (0.951**). On the other hand, all sulfides decreased significantly (P ≤ 0.01**). Changes in vanillin, guaiacol, 4‐vinylguaiacol (4‐VG) and 4‐ethylguaiacol (4‐EG) also suggested a potential synthesis during the aging process. The results of PCA and CA demonstrated that Chinese rice wines with different ages could be clearly distinguished from each other, which was consistent with the evolution of the 49 aging markers during the aging process. CONCLUSION These 49 potential ‘aging markers’ successfully distinguished ages using PCA and CA. Our results therefore throw light on the characterization of VOCs during Chinese rice wine aging, and provide a quantitative basis for discriminating the ages of Chinese rice wine. © 2019 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Characterization of volatile organic compounds as potential aging markers in Chinese rice wine using multivariable statistics

2019

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“…Values in the same row that do not share a common letter are significantly different (p > 0.05). Sensory threshold values from literature ( 21, 23, 24 ) . *Bottle refermented beers…”

Section: Resultsmentioning

confidence: 99%

“…In this case neither the cysteinylated nor the glutathionylated S-conjugate have been found in hops. This constitutes the first (21,23,24). *Bottle refermented beers Thiols from Mandarina Bavaria in late-hopped beers evidence that malt could be a significant contributor of 3S4MPol.…”

Section: Free Polyfunctional Thiols Transferred To Beer By Late Hoppingmentioning

confidence: 91%

Ability of the Mandarina Bavaria hop variety to release free odorant polyfunctional thiols in late‐hopped beers

Chenot

Collin

2021

J. Inst. Brew.

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The cysteinylated and glutathionylated precursors of 3‐sulfanylpentanol (Cys‐3SPol up to 197 μg/kg, G‐3SPol up to 14 mg/kg), recently reported in hops, were quantitated for the first time in the Mandarina Bavaria variety, along with the ubiquitous cysteinylated and glutathionylated forms of 3‐sulfanylhexanol (Cys‐3SHol up to 897 μg/kg, G‐3SHol up to 46 mg/kg). In contrast to findings with another new German cultivar, Polaris, no trace of 3‐sulfanyl‐4‐methylpentanol adducts (Cys‐ and G‐ 3S4MPol) was found. To assess the transfer rate of thiols from hops to finished beer, the same pilot Mandarina Bavaria hopped wort was fermented with two different dry yeasts, bottle refermented or not, and analysed. The data were compared with results obtained for a similarly produced commercial beer. In conclusion, despite significant variation between harvest years, Mandarina Bavaria appears not to contain outstanding amounts of free thiols or thiol S‐conjugates. Its S‐conjugate pool is sufficient, however, to bring 3SHol above its odour threshold. This work also suggests that since 3S4MPol was found near or above its threshold in most late‐hopped beers it does not originate from hops and that malt may be its main contributor. © 2021 The Institute of Brewing & Distilling

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“…3 Forty-one volatile polyfunctional thiols have been found in hop, and each cultivar exhibits a unique thiol profile. 3−5 3-Sulfanyl-4-methylpentan-1-ol (26) with grapefruit-/rhubarb-like flavors (odor perception threshold = 70 ng/L in beer) 5 was previously proposed as one of the key compounds contributing to the "Sauvignon Blanc-like" note imparted to beer by Nelson Sauvin hop. 5 Although relatively poor in other polyfunctional thiols, the Hallertau Blanc cultivar proved to be still much richer in 26, with concentrations up to 109 μg/kg, compared to 25−46 μg/kg in Nelson Sauvin, Mosaic, and Amarillo hops.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Reference Compounds Synthesized in Our Laboratory prior to This Study. 3-Sulfanyl-4-methylpentan-1-ol (26) was synthesized according to the method of Takoi et al 5 S-3-(1-Hydroxyhexyl)cysteine (Cys-23) was synthesized according to the method of Gros et al 10 Hop Samples. Amarillo and Mosaic hops bred in the United States were provided by Yakima Chief (Belgium).…”

Section: ■ Introductionmentioning

confidence: 99%

3-Sulfanyl-4-methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.)

Cibaka

Decourrière

Lorenzo-Alonso

et al. 2016

J. Agric. Food Chem.

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Monovarietal dry-hopped beers were produced with the dual-purpose hop cultivars Amarillo, Hallertau Blanc, and Mosaic. The grapefruit-like 3-sulfanyl-4-methylpentan-1-ol was found in all three beers at concentrations much higher than expected on the basis of the free thiol content in hop. Even cysteinylated precursors proved unable to explain our results. As observed in wine, the occurrence of S-glutathione precursors was therefore suspected in hop. The analytical standards of S-3-(4-methyl-1-hydroxypentyl)glutathione, never described before, and of S-3-(1-hydroxyhexyl)glutathione, previously evidenced in grapes, were chemically synthesized. An optimized extraction of glutathionylated precursors was then applied to Amarillo, Hallertau Blanc, and Mosaic hop samples. HPLC-ESI(+)MS/MS revealed, for the first time, the occurrence of S-3-(1-hydroxyhexyl)glutathione and S-3-(4-methyl-1-hydroxypentyl)glutathione in hop, at levels well above those reported for their cysteinylated counterparts. S-3-(1-Hydroxyhexyl)glutathione emerged in all cases as the major adduct in hop. Yet, although 3-sulfanylhexan-1-ol seems relatively ubiquitous in free, cysteinylated, and glutathionylated forms, the glutathione adduct of 3-sulfanyl-4-methylpentan-1-ol, never evidenced in other plants up to now, was found only in the Hallertau Blanc variety.

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

Cited by 11 publications

References 29 publications

Characterization of volatile organic compounds as potential aging markers in Chinese rice wine using multivariable statistics

Characterization of volatile organic compounds as potential aging markers in Chinese rice wine using multivariable statistics

Ability of the Mandarina Bavaria hop variety to release free odorant polyfunctional thiols in late‐hopped beers

3-Sulfanyl-4-methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.)

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