2016
DOI: 10.1021/acs.jafc.5b05733
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Identification and Organoleptic Contribution of Vanillylthiol in Wines

Abstract: Vanillylthiol, a chemical compound reminiscent of clove and smoke, has been identified for the first time in young red and dry white wines. The chemical structure of this new aroma was confirmed by original chemical synthesis. Vanillylthiol was prepared by a two-step procedure from vanillin. The conversion of vanillin to divanillyl disulfide was easily achieved by treatment with an inorganic sulfur-donor reagent. Reduction of the disulfide gave the target thiol in good yield. The quantification of vanillylthio… Show more

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Cited by 17 publications
(15 citation statements)
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References 41 publications
(85 reference statements)
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“…2-FMT, with a very low perception threshold (0.4 ng/L) and its distinguishable odor of coffee [50], is the key aroma compound of the boisée aroma of wines. A similar biosynthetic mechanism has been hypothesized for the formation of benzenemethanethiol, characterized by subtle mineral notes, starting from benzaldehyde [51] and for vanillylthiol, a chemical compound reminiscent of cloves, and smoke originating from vanillin [52].…”
Section: Factors Affecting Xylovolatiles Compounds During Winemakingmentioning
confidence: 65%
“…2-FMT, with a very low perception threshold (0.4 ng/L) and its distinguishable odor of coffee [50], is the key aroma compound of the boisée aroma of wines. A similar biosynthetic mechanism has been hypothesized for the formation of benzenemethanethiol, characterized by subtle mineral notes, starting from benzaldehyde [51] and for vanillylthiol, a chemical compound reminiscent of cloves, and smoke originating from vanillin [52].…”
Section: Factors Affecting Xylovolatiles Compounds During Winemakingmentioning
confidence: 65%
“…The recommended identification F I G U R E 7 Illustration of (a) typical GC-EI-MS total ion chromatogram (TIC) showing baseline noise and identifiable peaks; (b) illustration of a GC-EI-MS spectra showing maximum allowed tolerance for diagnostic ions; (c) experimental SIM and SRM chromatograms showing higher selectivity of SRM than SIM. Reproduced with permission from Floch et al (2016). Copyright 2016 American Chemical Society; (d) a panel of GC-EI-MS extracted ion chromatograms (EICs) of coinjection experiment to verify identification.…”
Section: Gc-msmentioning
confidence: 99%
“…Recently reported untargeted screening protocols are able to reveal more new volatiles F I G U R E 3 Volatile constituents identified from wine: selected wine volatile compounds identified from 1967 to 2020. References: 1: (Van Wyk et al, 1967b), 2: (Dubois et al, 1971), 3: (Schreier et al, 1974), 4 and 5: (Schreier & Drawert, 1974b), 6: (Simpson et al, 1977), 7: (Simpson, 1978), 8: (Buser et al, 1982), 9: (Masuda & Yunome, 1984), 10: (Harris et al, 1987), 11: (Darriet et al, 1995), 12: (Tominaga et al, 1996), 13-16: (Guth, 1997), 17-20: (Tominaga et al, 1998), 21 and 22: (Lavigne et al, 1998), 23: (Bouchilloux, Darriet, Henry et al, 1998), 24: , 25: (Tominaga et al, 2000), 26: (Darriet et al, 2000), 27: (Aznar et al, 2001), 28: (Herve et al, 2003), 29: (Tominaga et al, 2003), 30: (Janusz et al, 2003), 31: (Simpson et al, 2004), 32-34: , 35-37: (Campo, Ferreira, López et al, 2006), 38: (Bailly et al, 2006), 39-41: (Sarrazin et al, 2007), 42: (Wood et al, 2008), 43: (Culleré et al, 2008), 44: (Pons et al, 2008), 45: , 46: (Nikolantonaki & Darriet, 2011), 47: (San-Juan et al, 2012), 48: (Falcao et al, 2012), 49: (Stamatopoulos et al, 2014), 50: (Antalick et al, 2015), 51: (Floch et al, 2016), 52 and 53: (Pavez et al, 2015), 54: (Pons et al, 2016), 55-57:…”
Section: Overview Of Wine Volatile Constituents and Associated Identi...mentioning
confidence: 99%
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“…Other than retention index, MS spectra of peaks of interest can be compared to those in commercial databases (e.g., NIST [67] or Wiley [68]), or an in-house thiol database [23]. Accordingly, identity confirmation of new thiols then necessitates the synthesis of reference standards if they are not readily available from commercial suppliers [23,64,69]. The majority of GC-based quantitative analyses are conducted with MS detectors, with electron ionisation (EI) (Table 2, multiple entries) or less frequently used chemical ionisation (CI) (Entries 3, 5, 7, 8, 12) [18,25,29,30,31] being applied for volatile thiol detection.…”
Section: Analytical Instrumentationmentioning
confidence: 99%