Mercaptans from Aldehydes

Kipnis, Frank; Levy, Isidore.; Ornfelt, John

doi:10.1021/ja01174a533

Cited by 2 publications

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“…■ RESULTS AND DISCUSSION Chemical Synthesis. Vanillylthiol was mentioned in 1949 by Kipnis et al, 22 who studied the preparation of aromatic and heterocyclic thiols by the interactions of aldehydes with hydrogen disulfide. This was the only time when vanillylthiol was reported, and it was characterized simply by elemental analysis and refraction index, methods that are clearly insufficient for strict structural identification.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…30,31 Alternatively, thiourea can also be used as an odorless sulfur reagent to convert alcohols to the corresponding thiols via the basic hydrolysis of the unstable isothiouronium salt. 23 As a single procedure described in literature for vanillylthiol preparation cannot be considered as safe and environmentally friendly, 22 using thiourea as sulfur atom source in reaction with vanillyl alcohol 3, which was obtained by the reduction of vanillin with sodium borohydride in methanol, as previously described by Feng, 32 was chosen as the first approach (Figure 1). In our case, the target thiol vanillylthiol 2 and its corresponding disulfide 1 were obtained only at trace amounts.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

“…4-Hydroxy-3-methoxybenzenemethanthiol (Vanillylthiol) is a sulfur organic compound (2) described for the first time in 1949 by Kipnis. 22 Its structure was validated with no convincing instrumental results compared to those of the current analytical tools. Moreover, the presence of vanillylthiol in wine and in general in food and beverages has never been reported.…”

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Identification and Organoleptic Contribution of Vanillylthiol in Wines

Floch

Shinkaruk

Darriet

et al. 2016

J. Agric. Food Chem.

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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 vanillylthiol in wine was performed by nonspecific liquid/liquid extraction (CH2Cl2), separation of the volatile compounds using gas chromatography, and specific detection using tandem mass spectrometry (triple quadrupole). Vanillylthiol was found particularly in young wines aged in new oak barrels. These wines contained between a few 50 ng/L to more than 8300 ng/L. The highest levels were found in red wines aged 12 months in new oak barrels. Given its perception threshold in a wine model solution (3.8 μg/L), vanillylthiol may contribute to the spicy, clove-like flavor of red wines aged in oak barrels.

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Section: ■ Materials and Methodsmentioning

confidence: 99%