Dimethyl disulphide

Manufactured by Merck Group

Sourced in United States

Dimethyl disulphide is a colorless, volatile organic compound with a characteristic garlic-like odor. It is commonly used as a laboratory reagent and in various industrial applications.

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6 protocols using dimethyl disulphide

Development and Validation of TD-GC-qMS Method

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The TD-GC-qMS method development was done using dimethyl sulphide (1, anhydrous, ≥ 99%), 2-methylbutanal (2, 95%), dimethyl disulphide (3, ≥ 98%), 2-hexanone (4, analytical standard), 1-octanol (6, anhydrous, ≥ 99%), 2-nonanone (7, ≥ 99%), 1-undecene (8, 97%), 1-decanol (9, ≥ 9 8%) and 2-aminoacetophenone (10, analytical standard) purchased from Sigma-Aldrich (Taufkirchen, Germany), and 2-heptanone (5, ≥ 98%) purchased from Merck KGaA (Darmstadt, Germany).
To verify the analysis of cyclic siloxanes by atmospheric pressure ionization (APPI), coupled with thermogravimetry (TG) and a qMS, three cyclic siloxanes were analysed as single standards. Octamethylcyclotetrasiloxane (D4, 98%, Alfa Aesar, Karlsruhe, Germany), decamethylcyclopentasiloxane (D5, 97%, Alfa Aesar, Karlsruhe, Germany) and dodecamethylcyclohexasiloxane (D6, 95%, Alfa Aesar, Karlsruhe, Germany) were used.
For all purposes, liquid chromatography-mass spectrometry (LC-MS) grade methanol from VWR (Leuven, Belgium) and ultrapure water, generated with a water purification system from Sartorius Stedim (Göttingen, Germany), were used. For cleaning purpose, Decon 90 from VWR (Leuven, Belgium) was used.

Koehler T., Ackermann I., Brecht D., Uteschil F., Wingender J., Telgheder U, & Schmitz O.J. (2020). Analysis of volatile metabolites from in vitro biofilms of Pseudomonas aeruginosa with thin-film microextraction by thermal desorption gas chromatography-mass spectrometry. Analytical and Bioanalytical Chemistry, 412(12), 2881-2892.

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Synthesis of Octadecenyl Acetates

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Dimethyl disulphide (DMDS), n-octadecyl acetate (18:Ac)and farnesals were purchased from Sigma-Aldrich. (Z)-13-Octadecenyl acetate (Z13-18:Ac) and (E)-13-octadecenyl acetate (E13-18:Ac) had been synthesized previously in our laboratory, (Z)-2-octadecenyl acetate (Z2-18:Ac) and (E)-2-octadecenyl acetate (E2-18:Ac) were obtained by stereoselective reduction of the acetylenic alcohol precursor with hydrogen/Lindlar catalyst and lithium aluminum hydride, respectively. (E)-3-Octadecenyl acetate (E3-18:Ac) was prepared by reduction of the tetrahydropyranyl ether-protected acetylenic precursor with sodium in ammonia. (Z)-9-Octadecenyl acetate (Z9-18:Ac) was obtained commercially from TCI Europe. E2,Z13-18:OH and its acetate (E2,Z13-18:Ac) were kindly provided by Sociedad Española de Desarrollos Químicos (SEDQ, Barberà del Vallès, Barcelona, Spain).

Quero C., Sarto i Monteys V., Rosell G., Puigmartí M, & Guerrero A. (2017). Sexual communication in castniid moths: Males mark their territories and appear to bear all chemical burden. PLoS ONE, 12(2), e0171166.

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Comprehensive Flavor Compound Reference Protocol

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Reference standards (+) -β-Pinene (≥98.5%), 1-Octen-3-ol, borneol (≥95%), butyric acid (≥99.5%), citral (≥95%), cis-3-hexen-1-ol (≥98%), diacetyl, dimethyl sulphide, dimethyl trisulphide (≥98.5%), 3-methylbutanal (≥97%), 2-methylbutanal (≥95%), ethyl 2-methylbutanoate (99%), ethyl 2-methylpentanoate (internal standard, ≥99%), ethyl-3-methylbutanoate (≥98%), 3-methylbutyl-2-methylpropanoate (≥98%), 2-methylbutyl-2-methylpropanoate (≥95%), and ethyl cinnamate (99%), ethyl 2-methylpropanoate (≥99%), ethyl 3-methylbutanoate (≥98%), ethyl 4-methylpentanoate (≥97%), ethyl butanoate (≥99,5%), ethyl hexanoate (≥99.5%), eugenol (99.6%), furaneol (≥99%), geraniol (≥99%), hexanol (≥99%), 3-methylbutyl acetate (≥97%), linalool (97%), menthol (99%), methyl nonanoate (≥99.8%), myrcene (≥90%), geranyl acetate (≥97%), dimethyl disulphide (≥90%), limonene (97%), hexanal (≥98%), 3-hexenol (≥95%), 2-phenyl ethanol (≥99%), β-caryophyllene (≥80%), α-humulene (≥96%), humulene oxide, S-methyl 5-methylpentanthioate S-methyl hexanthioate, S-methyl 4-methylpentanoate and theaspirane (≥90%) were purchased from Sigma Aldrich (St. Louis, MO, USA).

Machado JC J.r., Lehnhardt F., Martins Z.E., Faria M.A., Kollmannsberger H., Gastl M., Becker T, & Ferreira I.M. (2021). Sensory and Olfactometry Chemometrics as Valuable Tools for Assessing Hops’ Aroma Impact on Dry-Hopped Beers: A Study with Wild Portuguese Genotypes. Foods, 10(6), 1397.

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Synthesis and Characterization of Fatty Acid Derivatives

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Dimethyl disulphide, iodine, 9cis-hexadecenoic acid methyl ester and the other commercially available cis and trans FAMEs and CEs were commercially available (Sigma Aldrich, Milan) and used without further purification. Pure samples of 6cis-16:1 and 7cis-16:1 were also commercially available (Lipidox, Sweden). Chloroform, methanol and n-hexane (HPLC grade, Merck) were used without further purification. Non-commercially available trans isomers as standard references were prepared and analyzed as previously described [22 (link), 28 (link)–30 (link)].

Sansone A., Tolika E., Louka M., Sunda V., Deplano S., Melchiorre M., Anagnostopoulos D., Chatgilialoglu C., Formisano C., Di Micco R., Faraone Mennella M.R, & Ferreri C. (2016). Hexadecenoic Fatty Acid Isomers in Human Blood Lipids and Their Relevance for the Interpretation of Lipidomic Profiles. PLoS ONE, 11(4), e0152378.

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Measurement of Sulfur Compounds in Wine

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M ethanol, ethanol, acetonitrile, dichloromethane, riboflavin, citric acid, tartaric acid, boric acid, mercaptoethanol, o-phtaldehyde (OPA), amino acid multi standard (containing acidic, neutral, and basic amino acids), riboflavin (RF), d₆-dimethyl sulphide (d₆-DMS), isopropyl disulphide, dimethyl disulphide (DMDS), dimethyl trisulphide (DMTS), p-benzoquinone (pBQ), 3-mercaptopropanoic acid (3MPA), glutathione, trifluoroacetic acid and hydrochloric acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium metabisulfite was purchased from J.T. Baker (Deventer, The Netherlands). All the chemicals were of analytical grade, at least. HPLC grade water was obtained by a Milli-Q system (Millipore Filter Corp., Bedford, MA, USA).
Commercial hydrolysable tannins from chestnut wood intended for oenological use were provided by Dal Cin (Concorezzo, Italy).
The model wine solution (MW) was made of 5.0 g/L tartaric acid and 12% ethanol (v/v), adjusted to pH 3.2 with sodium hydroxide (Merck, Darmstadt, Germany).
The white wine (WW₀) produced with Trebbiano grape in vintage 2016 was collected at a local winery just after bottling and analyzed. The concentration of Met in WW₀ was 5.90 ± 0.35 mg/L and that of total SO₂ was 80 ± 2 mg/L, while no RF nor GSH were detected.

Fracassetti D., Limbo S., Messina N., Pellegrino L, & Tirelli A. (2021). Light-Struck Taste in White Wine: Protective Role of Glutathione, Sulfur Dioxide and Hydrolysable Tannins. Molecules, 26(17), 5297.

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Analytical Procedures for Tannin-Rich Samples

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M ethanol, ethanol, acetonitrile, riboflavin, citric acid, tartaric acid, tetrahydrofuran (THF), boric acid, mercaptoethanol, o-phtaldehyde (OPA), L-methionine, d 6 -dimethyl sulphide (d 6 -DMS), isopropyl disulphide, dimethyl disulphide (DMDS), dimethyl trisulphide (DMTS), Folin-Ciocalteu reagent, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydrochloric acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). All the chemicals were of analytical grade, at least. HPLC grade water was obtained by a Milli-Q system (Millipore Filter Corp., Bedford, MA, USA).
Commercial hydrolysable tannins from nut galls, chestnut and oak woods intended for oenological use were provided by Dal Cin (Concorezzo, Italy).
The model wine contained 5.0 g/L tartaric acid and 12% ethanol (v/v), adjusted to pH 3.2 with sodium hydroxide (Merck, Darmstadt, Germany).

Fracassetti D., Limbo S., Pellegrino L, & Tirelli A. (2019). Light-induced reactions of methionine and riboflavin in model wine: Effects of hydrolysable tannins and sulfur dioxide. Food chemistry, 298.

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